Over the course of a decade, Saturday Night Live’s Digital Shorts became a groundbreaking way to bring sketch comedy to the world in bite-size chunks. What started off as just a few of the show’s writers and cast members going off to do their own thing became the most anticipated and beloved segment of the show going into the new millennium, and is often cited as one of the primary reasons Youtube took off.
In the span of just a few minutes, the Digital Shorts could get in and get out with a strange, witty idea, without overstaying its welcome—a problem SNL has always had. By the second one, the Digital Short became a huge hit, revitalizing Saturday Night Live and bringing a fresh new style of humor that still resonates long after the show’s shorts creators have moved on.
The three primary short creators—Andy Samberg, Akiva Schaffer and Jorma Taccone—, a comedy rap group that would become almost as popular as the shorts themselves. With the first Lonely Island film Popstar: Never Stop Never Stopping on the way later this year, let’s take a look at the Digital Shorts from worst to best—all 104 of them.
The premise of “Daiquiri Girl” is that the original idea would have featured that week’s musical guest Gnarls Barkley, but when they bailed, Akiva Schaffer and Andy Samberg got drunk and made this terrible ‘90s music video, as Samberg sings a terrible song while dressed sort of like an early version of Shy Ronnie. While that is the joke, “Daiquiri Girl” is so bad, it’s hard not to imagine that this must be somewhat based in truth. The Digital Shorts have done intentionally bad before in hilarious ways, but “Daiquiri Girl” is just bad bad. Watch it here.
One of only two Digital Shorts to be written by Jorma Taccone and Akiva Schaffer without Andy Samberg, “Hey! (Murray Hill)” just really doesn’t have much going for it. As a sort of parody of CW teen dramas, James Franco plays a man who can’t quit telling a woman (Kristen Wiig) that comes up to him about his tiny ding-dong. That’s about it. Eventually Blake Lively shows up to mention she also has a tiny ding-dong as they leave together, but there’s really nothing beyond that. “Hey! (Murray Hill)” doesn’t work as a parody of the shows it’s mimicking and the one joke it has to tell never really works.
You see that title? That’s all you need to know really. “Convoluted Jerry” is a singer whose songs are convoluted. Barely over a minute, “Convoluted Jerry” easily overstays its welcome and not even a cameo by Charles Barkley singing a duet and an explanation of Inception can save “Convoluted Jerry.”
“Golden Girls Theme” starts off incredibly cheesy, as the cast of SNL sings the theme of Betty White’s show to her in a sign of appreciation, then only gets worse as the style changes abruptly. When White sings her own version, she puts on a black ski mask and sings her death-metal version of the same theme, complete with moshing and violence. But the worst part of “Golden Girls Theme” is how every aspect of it feels false, as the cast singing seems forced and awkward, while the last half’s too reliant on the idea of “isn’t it funny to watch older people to crazy things?”
After “Convoluted Jerry,” there were almost two months of no Digital Shorts—one of the biggest gaps during the show’s Digital Short period. When the shorts did come back, it did so with “Afros,” a song about a couple (Samberg & Wiig) who share one gigantic afro. Like “Convoluted Jerry,” there’s no larger idea and not really any clever twist on the idea. “Afros” is simply one joke without anything deeper to make the short worthwhile.
“Wow I did not like that,” Kenan Thompson says after hearing “Please Don’t Cut My Testicles,” a song by a C+C Music Factory/Right Said Fred pastiche Ariel (Andy Samberg) and Efrim (Tom Hanks). And who can blame Kenan? Most of the humor here comes from watching Tom Hanks singing while wearing leather pants and a bald cap and the basic joke never escalates, only repeating its idea over and over. “Please Don’t Cut My Testicles” is the first swing-and-a-miss for the Digital Shorts and is by far the worst of the short’s first season batch. Watch it here.
Andy Samberg along with The Lonely Island would eventually find success with poor fashion choices (“Turtleneck & Chain”), but their first attempt, “The Best Look in the World” (dress shirt, black socks and no pants) is pretty bad. The country song at the core of “The Best Look in the World” is borderline “Daiquiri Girl” bad, but kudos to Shia LaBeouf for going all-in and trying to sell this thing with all he’s got. Watch it here.
Whew boy, season 36 started off with a series of misfires that never quite found the ideal combination of concept and humor. “Relaxation Therapy” is the worst of season 36’s early shorts, as Jane Lynch plays a therapist using a new type of therapy on her subject that involves toplessly feeding him popsicles and kicking him in the crotch while she tries to place him in a zone of relaxation. Like many of the shorts that start off this season, there’s an interesting premise deep in there, but the result of the idea just doesn’t work. Watch it here.
After a spectacularly strong season of Digital Shorts, “Cherry Battle” is one of the final ones of season 35 and also the weakest. Andy Samberg and Gabourey Sidibe spit cherries at each other and catch them in their mouths. The end. If anything, this seems like directors Akiva Schaffer and Jorma Taccone figured out how to use slow-motion and trick photography and wanted to show it off. Watch it here.
“I Broke My Arm” is one of the rare Digital Shorts that doesn’t get funnier the weirder it gets. “I Broke My Arm” has Emma Stone as a high school student bragging about how she broke her arm after slipping on grape jelly, then continuously keeps tripping, breaking other limbs, until she’s in a wheelchair, using a computer to talk. If it stopped right there, it would’ve been fine, but then the grape jelly comes to life, not really adding anything to the short other than taking it down a strange path that isn’t even funny. Watch it here.
“Nurse Nancy” is so close to the truth, it’s almost not a joke at all. Sure, “Nurse Nancy” is a parody of Eddie Murphy films, as Andy Samberg plays every character in the fake film, including a toaster, Mayor McCheese and Sean Penn. But in hindsight, it’s also hard to not think about how close Samberg was to getting caught up in this type of film as well, since he would often collaborate with Adam Sandler, who pulled this stunt with Jack & Jill. Watch it here.
“The Mirror” takes the horror movie jump scare and surprise nightmares and runs them into the ground through repetition and random surprises. Usually the Digital Shorts can make repetition and randomness work, but “The Mirror” wears out its short running time much quicker than expected, while never getting much funnier beyond the initial joke.
It’s not very often that a Digital Short centers around a song that just does not work, but “Hero Song” is a rare example of that. Samberg plays a Bruce Wayne-type that sings about how New York needs a hero, turns into a superhero and then gets the crap kicked out of him. The initial joke comes in about halfway though, then just repeats the idea over and over and over. The audience reaction is the right one, as there’s a huge surge of laughter with the first punch, followed by a quick petering out as they realize this is all there is to this short. Watch it here.
“Wish It Would Rain” is like a slightly better “Daiquiri Girl,” as Samberg sings about being alone, but then gets angry when despite the forecast, it won’t rain for his video. Instead of building, “Wish It Would Rain” just falls flat, which leaves Samberg’s singer to insult his producer and make fun of his assistant’s butt—played by Emma Stone. “Wish It Would Rain” feels so thin and never really amounts to much beyond the concept. Watch it here.
The first of many incredibly weird shorts directed and co-written by John Solomon, “The Date” has Will Forte—who has a high-pitched voice—on a night out with Megan Fox—who is way more into the date than Forte is. Usually the shorts that center on Forte are winners, but “The Date” is little more than a funny voice and would be overshadowed by a much better short, “Megan’s Roommate,” also starring Fox, that would occur on the same episode.
After the late ‘80s-early ‘90s VHS style of “Body Fuzion,” Drew Barrymore’s next hosting episode returns to this style with “Brenda & Shaun,” about a duo of laser magicians (Barrymore and Fred Armisen) who are good for events, but then end up going bankrupt and performing on the street, since how much demand is there for laser magicians? “Brenda & Shaun” combines the talents of Barrymore and Armisen well and the devolution of their career is funny, but the best parts here come from the reactions of people who just want Brenda & Shaun to go away, rather than anything Barrymore and Armisen are doing. Watch it here.
While writing for Saturday Night Live, John Mulaney helped write only two Digital Shorts, one of which is this strange one, “The Other Man.” In the skit, Ryan Phillippe keeps going to the homes of people like his ex, his parents and his best friend, only to discover the same odd man—played by Andy Samberg—is sleeping with all of them. Samberg’s character here just isn’t as funny as he should be. Even though the concept has potential, it doesn’t quite work as well as it should. Watch it here.
In Andy Samberg’s final season of Saturday Night Live, the Digital Shorts would become less of a combination of The Lonely Island and more about the team of Samberg and writer-director John Solomon. Their first short working solely together, “V-Necks” isn’t exactly a stand out, as Samberg and host Ben Stiller have a battle to wear deeper and deeper V’s. Once it gets going, it’s pretty clear where this skit is going to end up. There’s no reason why Stiller doesn’t play Derek Zoolander in this skit, especially since he reprised in the same episode. Watch it here.
Like “Pep Talk,” the previous short that Fred Armisen had written, “Cookies” fits Armisen right into his wheelhouse, giving him a scenario, then letting him basically run it into the ground with different approaches. “Cookies” also marks the only short co-written by SNL writer James Anderson, but it largely feels like the work of Armisen. Like most shorts written by Armisen, “Cookies” seems like the type of material he’d later go on to write for Portlandia.
The majority of “Rescue Dogs 911 App” comments on the frustration of pop-up adds in various apps and isn’t particularly funny. Yet it’s when the “rescue dog” appears to help Samberg—whose house is getting broken into—that “Rescue Dogs 911 App” rescues itself, as a cute dog bites off a criminal’s arm, before giving Samberg a high-five. Like “Boogerman” before it, “Rescue Dogs 911 App” has a decent concept that doesn’t really work until the very end. Watch it here.
The SNL 40th Anniversary Special was a way for Saturday Night Live to pay homage to itself, often by cramming in various generations of jokes into one specific type of bit. Sometimes it worked, as with Celebrity Jeopardy, and sometimes it didn’t, like with this Digital Short. “That’s When You Break” barely even has any jokes, instead showing moments where people laughed during sketches without context. As Andy Samberg and Adam Sandler sing about these moments, there are aspects that work, like constantly pointing out how Horatio Sanz and Jimmy Fallon could keep a straight face together, or reminding everybody how bad That’s My Boy bombed. But really, “That’s When You Break” ends up being a self-indulgent reference-fest that feels made for coworkers and no one else.
Another dumb idea that’s too much fun to not love, Neil Patrick Harris teams up with the entire cast to perform the “Doogie Howser Theme.” Each member of the cast is dressed like Doogie Howser, M.D., as the band grows throughout the song until Harris sheds a tear in the video’s final moment. It’s always great to see Harris embrace his past and the theme is a reminder of how great ‘80s-‘90s TV themes used to be. Next, SNL needs to get Bronson Pinchot on for a Perfect Strangers theme short. Watch it here.
The second season of Digital Shorts doesn’t start out too strongly with “Cubicle Fight,” as Bill Hader and Dane Cook have—as the title implies—a cubicle fight. The first short written and directed solely by Akiva Schaffer doesn’t pay off until the fight concludes with an insane burst of violence after the mostly playful fight. “Cubicle Fight” also does have a fun little inside joke, as Jason Sudeikis’ boss character keeps stopping by, asking for the “Higgins report,” a reference to writer and The Tonight Show with Jimmy Fallon announcer Steve Higgins.
“Boogerman” is one of the grosser Digital Shorts. At an awards show Katy Perry sings the theme song to the superhero film of the same time (which may or may not be based on the ‘90s videogame character). “Boogerman” is a decent take down of the ridiculous musical interludes at award shows, but when you consider the embarrassment of riches that were the cameos in this episode (Amy Poehler & Peter Sarsgaard appear in the short, while Justin Timberlake, Jimmy Fallon, Tina Fey, Rachel Dratch and Maya Rudolph all appeared in the episode proper), “Boogerman” seems like a missed opportunity. Watch it here.
Airing on the same night as “Laser Cats 7”—one of only three times an episode featured two Digital Shorts—“Gotye Backstage” is one of the few shorts that isn’t funny if you don’t understand the cultural reference that is being made fun of. Just five years later, Gotye’s video for “Somebody That You Used to Know” feels like an ancient reference to make and Gotye might be one of the only people ever in a Digital Short to almost break.
By 2011, parodying Stomp and The Blue Man Group seemed pretty dated, but “Stomp” is a decent way to combine these two shows in an explosive way. In hindsight, it’s funny to see Samberg in a police precinct prior to his role on Brooklyn Nine-Nine, almost making one wish that they could do this exact same bit on that show instead. Also interesting is seeing Fred Armisen as a member of The Blue Man Group, which he was a part of before he joined SNL Watch it here.
The best Digital Shorts often seem like someone had a great idea, then with only a few days to air, ran out with some friends to write and direct it. “Andy Popping into Frame” however feels more like the crew under an incredibly tight deadline pulling something out at the last second. The title gives away the entire joke, with the only real surprise coming from where and when Andy will pop up. As with every short he’s in, Will Forte steals the short when he starts trying to steal Samberg’s spotlight. Watch it here.
Hey remember that awful-looking Vanessa Hudgens/Alex Pettyfer retelling of Beauty and the Beast? No? Well no one can blame you. “Beastly” is one of the shorts that hasn’t aged all that well, specifically because the film it’s parodying was a huge bomb no one remembers and Miley Cyrus is always painful whenever she’s trying to be funny. But Samberg’s “beast” does save this dated parody, by being incredibly weird—which is almost always a great way for Samberg to save a short that doesn’t entirely work.
We should all be so lucky to have Will Forte narrate our lives using song. It sounds like the type of experience that would never get old. “A Couple of Homies” has Forte doing exactly this, as Andy Samberg and Fred Armisen engage in such mundane friendship activities as looking at a magazine, drinking sodas and putting on yellow dresses while they unpeel bananas and stare at each other. The whole bit ends up being a D.A.R.E. commercial, but if having Forte sing about your life is wrong, I don’t want to be right. Watch it here.
“Harpoon Man” ends up being one of the few short songs written by The Lonely Island that doesn’t really work, likely because it relies too greatly on the visual element. John C. Reilly plays the titular Harpoon Man in a Shaft parody, narrated by a whale (Samberg) who keeps insulting him. “Harpoon Man” is one of the few shorts that is weird, but doesn’t feel quite as weird as maybe it should be. Watch it here.
One of only two shorts co-written by John Lutz, “Pep Talk” is one of the few early Digital Shorts that almost seems like it was originally planned as a skit on the actual show. At a fast food restaurant, Fred Armisen (also co-writing) plays a boss who just can’t handle any interruptions, threatening to shut up his employees by using physical violence. Armiesen excels in this type of situation where, like “The Tangent,” he’s allowed to go off in whatever direction he feels like, but it’s slightly surprising fodder for one of the shorts.
“Firelight” is one of only three shorts co-written by Seth Meyers and one of the few film parodies the Digital Shorts would ever make, this time making fun of Twilight, but with Frankenstein monsters. “Firelight” expertly matches the film’s tone, and Taylor Swift as the Bella surrogate nails the ticks of Kristen Stewart. So does Bill Hader, who captures the intensity of Edward, but as a member of the Frank family, who is known for accidentally strangling people.
The last Lonely Island video to premiere on Saturday Night Live, “Hugs” encompasses the shortcomings of their Wack Album. As the Los Angeles Times said in their review of The Wack Album, “these Saturday Night Live veterans have become better rappers than comedians,” and the album “feels awfully short on fresh ideas.” “Hugs” proves all of this correct, as it is a better song than it is at dispensing jokes. Not only that, but the idea that the song is based on—that hugs are some sensual experience that the singer is overestimating the power of—is also an idea that was used to much better results by Flight of the Conchords.
“What Was That?”’s biggest problem is that at 2 1/2 minutes, it already seems too long. As a model U.N. goes to the actual U.N., Samberg and his student band sing a song asking the United Nations what’s the deal with all the negative things that have happened in the world. Right when you think it should end though, Arcade Fire come to party at the U.N. and dance. At about half the length, “What Was That?” would’ve been far better and not dragged out the joke as long as it does. Watch it here.
“Andy Walking” flips the basic premise of Jaywalking, making host Andy Samberg ask people basic questions—which they all know the answers to—yet Andy is too dumb to realize that the answers are right. Andy being incredibly stupid is often funny, as is making fun of the idea that everyone interviewed for these types of segments are idiots, yet for some reason “Andy Walking” doesn’t pop as much as it should, ending the first season of Digital Shorts on a mediocre point. Watch it here.
On The Lonely Island’s debut album “Incredibad,” the weakest song is “Ras Trent,” a song sung by a white college Rastafarian—of course played by Samberg—about his new religion. “Ras Trent” might also be too on-the-nose, as the song points out the ridiculous idiocy that comes in this caricature of a person. Maybe the most interesting aspect of “Ras Trent” is that Samberg’s future wife Joanna Newsom does backing vocals along with Maya Rudolph for the track.
“Jizz In My Pants” is the first Digital Short that feels more like a Lonely Island music video, as it’s also the first Digital Short to prominently feature Jorma Taccone and a cameo by Akiva Schaffer. Released as the first single for The Lonely Island’s Incredibad, “Jizz In My Pants” is one of the more basic songs on their debut album, as the idea is literally everything makes Samberg and Taccone jizz in their pants. While it was a huge hit for The Lonely Island, it just doesn’t have the wit of their other songs and unfortunately relies on repeating the same joke over and over, with increasing intensity.
Very often, the Digital Short can play off the strengths of its main actor. For example, “The Tangent” focuses on Fred Armisen and very much feels like it could’ve been a Portlandia skit. “The Tangent” allows Armisen to improvise whatever comes off his head and go off on, well, any tangent he can come up with. In only its fourth Digital Short, SNL has its first celebrity cameos, showing how big this endeavor has become in just a few months, with appearances by Scarlett Johansson (also the first time a host appeared in a short, despite not airing on her episode), Brian Williams, Conan O’Brien and Gideon Yago.
The only short written by Fred Armisen and Andy Samberg, “Get Out” meets both of their comedy styles right in the middle. Both often find their humor in repetition and the build-up of expectation that grows out of that repetition. As Armisen keeps walking in on Samberg while he’s on the toilet, “Get Out” allows for the combination of strangeness and repetitive retelling of the same joke that works great for both of them. Watch it here.
So many of the Digital Shorts focus around Samberg’s ignorance and his inability to understand the obvious statements people tell him. “Threw It On the Ground” continues this trend, as he turns down people’s kindness by throwing niceties on the ground that he’s offered, that is until Ryan Reynolds and Elijah Wood end up tasering him in the butthole, a punishment he pretty much deserves.
It’s sort of surprising just how few Digital Shorts exist that centered on Bobby Moynihan, especially considering how great he is in “Megan’s Roommate.” Somehow he’s convinced Megan Fox that he’s Optimus Prime, when he’s clearly just a roommate in a bathrobe that “transforms” into a naked dude. The sequence of him and Bumblebee (Brian Austin Green) transforming into nudity at the end of a transforming montage showcases the then-featured player Moynihan as one of the funniest members of the cast and the only featured cast member from that era that remains on the show today. Watch it here.
Despite being largely a parody group, “Like A Boss” is one of the few songs The Lonely Island made that is a direct parody of a specific song, rather than just a type of song. Based on Slim Thug’s “Like A Boss,” The Lonely Island’s version is just as ridiculous, but made even more so by Samberg’s overly confident delivery of stating how every day he cuts his balls off, gets rejected by Deborah at his office and flies into the sun, amongst other eventful things. Once again, it’s the rapid-fire insanity that makes “Like A Boss” so successful, as the craziness flies by as Samberg recites his day to Seth Rogen.
The only short written solely by Kristen Wiig, “Virgania Horsen’s Pony Express” feels so much like a Tim & Eric skit. Wiig’s bland delivery as Horsen has that Adult Swim feel that rarely ever shows up in the Digital Short—strange considering how many SNL alums have ended up working with Tim & Eric. But between writing this and co-writing “Body Fuzion,” it’s too bad Wiig never wrote more shorts, rather than just appearing in them. Watch it here.
“Peyote” essentially uses the same surprise ending at the first short “Lettuce,” which makes sense since the two shorts were shot around the same time. But unlike too many SNL segments, “Peyote” knows how to get its joke out there and get out, without overstaying its welcome. At less than a minute, it remains one of the shortest of the shorts, a quick little bit that is exactly as long as it should be. Watch it here.
It’s hard to end a trilogy in a satisfying way and “Laser Cats! 3D” is no exception. While “Laser Cats! 2” pushed the idea up a notch by pushing the poorly made aspects of the short and great cameos, “Laser Cats! 3D” ends up feeling more like the first installment—not a bad thing—but just not as funny. As Mayor Top-Hat (Kenan Thompson) makes laser cats illegal and plans to use the banned cats to take over the universe, Admiral Spaceship keeps hold of their cats to take on the evil mayor. While a Christopher Walken cameo and “impressive” 3D moments attempt to make “Laser Cats! 3D” the best in the bunch, it might be the most disappointing of the series. Watch it here.
Very much like “Talking Dog,” “Andy’s Dad”’s humor comes from an unexpected kiss. When host Jonah Hill admits that he’s dating Andy’s dad (played by SNL writer Jim Downey), the short mostly questions how far these two will go. The answer: an open mouth kiss that goes on way too long. For once, Andy gets to play the straight man, while Jonah goes all in with the bit as the new lovestruck boyfriend of Andy’s dad.
The Lonely Island often finds extreme repetition to be hilarious and often they’re right. But in “The Shooting,” a parody of the second season finale of The O.C., it never quite hit me as all that funny. Maybe it’s my love for The O.C. that blinded me to the humor, or maybe it’s the fact that the Virginia Tech shooting happened only two days after the first airing of the episode. Or maybe at this point it’s just because gun violence has gotten so out of control that “The Shooting” has become less funny over time. “The Shooting” on paper is a fun idea, but it’s also one of the few shorts that hasn’t aged all that well.
“Best Friends” finds a much better usage of Katy Perry than “Boogerman” and continues the tradition of having screwed up ideas for the holiday episode short, much like “Dick in a Box” or “The Tizzle Wizzle Show.” In “Best Friends,” Perry and Samberg are two friends singing about their friend activities, to be joined by a homeless meth addict (Matt Damon), and a mad time-machine-building scientist (Val Kilmer). The beginning and end of “Best Friends” are okay, but it’s the middle that shines, as the four friends play Russian roulette and the scientist unveils his bird man creature that just wants to die. Also, how has Matt Damon only hosted SNL one time? Doesn’t that seem like a huge oversight?
While not as great as The Lonely Island’s odes to sex in “Dick in a Box” and “Motherlover,” “I Just Had Sex” does take a far less confident look at the act of getting it on. As so many Lonely Island videos do, the joke here is just how incompetent these guys are, that despite how excited they are about getting to put their “penis inside of her,” they’ve failed at pleasing the women and lasting over a minute. “I Just Had Sex” also gives us the title to the group’s second album, as Jorma brags about how she let him do it while wearing his turtleneck and chain. Also fun is how Akon is used as a confidence booster for these two, who seems even happier about these two having sex than they are.
“Laser Cats, the Musical” is the only short of the series where the funniest aspects happen before and after the video Samberg and Hader have made that Lorne Michaels will hate. While Tom Hanks introduces the video, he disappointingly doesn’t make an appearance in the short—a huge missed opportunity, considering how funny he is in his back-and-forth with Michaels. But “Laser Cats, the Musical” does give us Elton John as the villainous Droz, who uses the power of music to turn laser cats evil. Getting John into this world of laser cats is funny on its own, but “Laser Cats, the Musical” unfortunately doesn’t do anything with the format that hasn’t been done better before. Watch it here.
The early seasons of the Digital Shorts always found a way to present a weird idea, make it seem almost normal in the moment, then expand on it in hilarious ways. In “Talking Dog,” Andy meets a dog that talks to him, trying to seduce him in order to use Andy as a way to get ham. Watching an adorable dog as Jorma pretends to be his voice is great, and it only becomes better when you realize the dog’s ultimate goals and that said dog is probably smarter than Andy. “Talking Dog” builds on its idea until it goes to the only possible place it could go, as Andy makes out with the dog.
The format of “A Brief Interview With Drake” is a great idea, and if it had come up earlier in Samberg’s time on SNL, it could’ve easily come back over and over. As the title implies, Samberg interviews Drake with different segments such as “An Extremely Sarcastic Interview,” “A Racist Interview” and a “Dark Interview,” told almost completely in the dark. “A Brief Interview With Drake” is so simple in its execution, but the way it’s handled gets funnier and stranger the longer it goes on. Watch it here.
The best thing James Cameron has done in decades, “Laser Cats 5” has the director helping Samberg and Hader with their epic series, while making fun of his entire filmography in the process. “Laser Cats” is always intentionally a mess, but the way it blends elements from Alien, Terminator, Avatar and Titanic into one jumbled video is incredible. When Admiral Spaceship shows up as a Na’vi, connecting his ponytail to a laser cat, it almost makes the three hours of your life you lost watching Avatar worthwhile.
Even though many of the songs that appear in the Digital Shorts are credited as from The Lonely Island and even appear on their albums, “The Creep” is the first Digital Short to present them together as a band. While not the first short to feature Akiva, Jorma and Andy together, it is the first song of theirs to equally distribute them and present all three together as one entity. But it’s Akiva who comes off the creepiest by far in “The Creep,” talking about how he’s been a creep since he popped out his mom like kettle corn. “The Creep” also uses Nicki Minaj’s various personalities well, as you could totally imagine her being a total creep, spying on boys in the locker room.
After the slight disappointment of “Laser Cats! 3D,” making a fourth one could’ve been a…cat-astrophe. But returning with executive producer Steve Martin, “Laser Cats! 4-Ever!” brings this series right back on top where it belongs. Having to fight a half-human, half-laser cat, half-Robocop named Cyberface, Nitro and Admiral Spaceship have to cut their Mars vacation short to take on this new villain, only to discover that they are brothers and that Cyberface is their father. “Laser Cats! 4-Ever” gets back to pointing out the ridiculously low-budget aspects that made the first two “Laser Cats” so great, while Hader and Samberg bring Steve Martin down with them, to the point that Lorne Michaels even turns his back on Martin. Watch it here.
The very first Digital Short, “Lettuce” doesn’t have quite the scope of later shorts and could’ve easily been a ten-to-one sketch. But “Lettuce” does showcase the strange brand of humor that will come quickly with later shorts, likely due to the always unusual writing from Will Forte. “Lettuce” hits exactly what the Digital Shorts should be right out the gate: an insane idea that should probably only sustain itself for two or three minutes, getting in and out as quickly as possible, but still becoming a highlight of every show.
“Extreme Activities Challenge” reminds a lot of “Andy Popping Into Frame” and “People Getting Punched Just Before Eating,” in that it’s a skit where we’re supposed to watch Andy Samberg do dumb things, while Will Forte steals the show. In “Extreme Activities Challenge,” Kristen Wiig and Samberg compete in such odd competitions as “hat balancing” and “becoming a human ATM.” But as the referee, Forte is hilarious when he loses the competition “look good while wearing stripes” and winning “become a referee in a desperate bid for human interaction.” But don’t worry, Samberg won the night’s spotlight back when he impersonated Mark Wahlberg and incurred his wrath later in the episode. Watch it here.
“Party Guys” utilizes the same rapid-fire series of characters that worked in “Business Meeting,” but takes it to another level by making literal representations of everyone. For example, “look at this bunch of jokers” is literally a group of people dressed like The Joker, or a turd burglar is actually a guy stealing turds from a toilet. “Party Guys” never gets as insane as “Business Meeting,” but instead gets contemplative with the criticism of the two party guys (Hader and Samberg) and their judgmental comments by saying “look at these two douchebags,” before we see they’re looking in a mirror. If anything, it’s a solid way to end a short, considering they usually just end in the weirdest way possible.
“3-Way (The Golden Rule)” isn’t close to as good as its predecessors “Dick in a Box” and “Motherlover,” almost feeling like a necessity to get one more of these shorts in while Justin Timberlake hosts when Andy Samberg is still in the cast. “3-Way” brings in Lady Gaga and finally addresses the love between Timberlake and Samberg, but it’s all just watered down compared to what we’ve heard before. The song isn’t close to as catchy and the jokes just aren’t as strong as they once were, even though “3-Way” did also end up getting nominated for an Emmy. It lost to another Justin Timberlake song from the same episode.
A gigantic step up from the “Hero Song”—the Digital Short’s last attempt at a Batman parody—“Batman” plays off the Dark Knight’s ability to pop up and disappear from Commissioner Gordon at any time. While it is funny to see Batman pop up during Gordon’s shower, while he makes love to his wife and during his prostate exams, it’s Batman’s reasons for showing up that are the real gems here. Samberg’s excuses when he shows up are so excellent, saying things like “The Riddler’s costume is weird!” or “The Penguin got a new credit card!” that they almost outshine the concept by themselves. Watch it here.
Samberg’s first short as a host and not as a cast member, “When Will the Bass Drop?” goes back to the build-up and insane payoff of many of his past Digital Shorts. Samberg plays Davvincii, an EDM DJ who drives his audience crazy as they wait for the beat to drop, then when the beat does drop, everyone’s heads explode and murder is all over the club. In fact, “When Will the Bass Drop?” shares quite a bit in common with “Everyone’s A Critic,” as the final moments of insane violence remind us of that earlier short and even reuses the same Indiana Jones joke that short also used.
“Seducing Women Through Chess” is like the second, much more improved draft of “Brenda & Shaun,” taking that ‘80s commercial aesthetic and increasingyl horrible incidents to much funnier lengths. The first half doesn’t do much, as Samberg’s creepy instructor teaches his audience how to seduce women through chess, checkers and Jenga. But when he gets to trying to impress women by eating glass and then trying to get a prostitute—played by Jason Segel—the real sadness and darkness of the skit’s humor comes out in great ways. Watch it here.
It’s surprising that “Shy Ronnie” was nominated for an Emmy for Outstanding Music, considering it’s a duet in which one of the singers can’t even be heard. “Shy Ronnie” gives Rihanna a chance to show how funny she can be, making little comments as she gets angrier as her partner refuses to speak up. But the great payoff here is when Ronnie actually lets loose, clearly afraid to be performing in front of Rihanna, as he furiously raps when she’s not around, almost like Michigan J. Frog in a red wig.
Between “Boombox” and releasing his own version of “I Wish It Was Christmas Today,” Julian Casablancas’ love of SNL tends to make some pretty great songs. “Boombox” sounds like one of Casablancas’ better solo songs, but injected with The Lonely Island’s weirdness. It’s not the concept of a boombox and the power within that makes “Boombox” so fun, it’s the small details, like the “Spanish guy doing the Bartman and especially Samberg’s utter disgust at how apparently boiled goose is served all over New York City.
Brian Williams was one of the weirder choices to host in the 33rd season, but man is that guy funny. Almost like Jon Stewart but, you know, a reporter more than a comedian (for the most part.) With “Brian Diaries,” we get a glimpse at Williams’s daily life, which includes waiting outside 30 Rock for people to notice him, throwing pennies at Al Roker and Matt Lauer during The Today Show and meditating while thinking of Bono telling him how cool he is. Co-written by Williams, the anchor proved he’s one of the more underrated SNL hosts, one that should be invited back immediately. Watch it here.
The first short from Portlandia, Baskets and Kroll Show creator Jonathan Krisel, “Booty Call” once again embraces the humor in putting two polar opposite character together. That dichotomy made so many season 35 shorts so wonderful. This time it comes from Alicia Keys calling a creepy, diaper-wearing, chafed-nippled guy named Lionel for a booty call. Like “The Date,” but much better, Keys is great in “Booty Call” for being way into whatever odd things Lionel can come up with, before he shoots her down, since he’s in the middle of an intervention during their “sexy” talk. Watch it here.
One of the too few Digital Shorts to come from an idea by female writers, “Helen Mirren’s Magic Bosom” takes Nasim Pedrad on a wonderful journey after she touches host Helen Mirren’s breasts. The voyage into Mirren’s boobs is expressed through an incredible montage of moments, such as Brendan Fraser’s terrifying award show laugh and Teen Wolf dunking. This montage overshadows what comes before and after, but the craziness of that montage is almost as magical as Helen Mirren’s bosom. Watch it here.
“People Getting Punched Just Before Eating” takes the basic outline of “Andy Popping Into Frame” and improves it greatly by adding tension and by letting it go off-the-rails in the end. The title says it all, of course, but with slight twists, like Andy eventually killing Will Forte after he gets outsmarted and then finally having Andy punch a zombie, before getting chased around the world, followed by a zombie dance. Unlike “Andy Popping Into Frame,” though, “People Getting Punched Just Before Eating” has a continual upward momentum and expectation that makes the concept far more interesting than it should be. Watch it here.
“That’s how it began, and that’s how I’m going to finish it,” is fittingly how Samberg’s final short as a cast member on SNL ends. The last few shorts during Samberg’s tenure absolutely feel like a greatest hits reel, going back to laser cats and dicks in boxes. Of course it makes sense that “Lazy Sunday 2” would be in the works, since it is the first huge Digital Short, but “Lazy Sunday 2” doesn’t recapture the magic in quite the same way. As Chris Parnell and Samberg go to see “Sister Act: The Musical,” they rap about going to brunch and sneaking Vermouth into the theatre. But the best parts of “Lazy Sunday 2” don’t retread the same idea—it’s when Parnell and Samberg get their own verses near the end where “Lazy Sunday 2” is really at its best. Watch it here.
After about four months with no winners, the Digital Shorts came back to end their run strong with “Tennis Balls,” literally a short about Jonah Hill getting hit in the testicles by tennis balls. “Tennis Balls” works because it gets the shorts back to being more than just a dumb idea and into a dumb idea that can build and sustain for more than a few minutes. As Hill continuously gets hit by tennis balls, the reasoning keeps getting crazier, until ghosts are throwing tennis balls him and after dying, Hill is brought back to life by doing the thing that caused him to die: continuously getting hit in the nuts by tennis balls. Sometimes all it takes is going back to what always worked in the first place to get back on track. And nut shots never hurt either. Watch it here.
It shouldn’t be a surprise that the first host to star in a Digital Short would be Steve Martin, since he is one of the most consistent and frequent hosts in SNL history. “Close Talkers” is the first of only three times when SNL would air two digital shorts in one night (this along with “The Tangent”) and is the last short that Will Forte would write by himself. But like his first short “Lettuce,” Forte succeeds with a combination of awkwardness and making everything feel slightly off, as Martin and Forte have an entire conversation with their mouths less than an inch away from each other. Forte would go on to co-write a few more shorts, but it’s a shame we didn’t get to see him experiment in this format more than he did. Watch it here.
In Digital Short fashion, “Doppelganger” starts off as a simple idea, with friends Will Forte, Seth Meyers and Andy Samberg looking for each other’s doppelganger, then escalates to a ridiculous point, with Forte not being able to tell the difference between Samberg and a bum played by Horatio Sanz, determined to kill the one that isn’t his friend and shooting the wrong person. In the first Digital Short written solely by The Lonely Island crew, “Doppelganger” feels like the first time we see their non-musical humor in a similar vein to what we’ll see in Hot Rod and MacGruber, just on a much smaller (but still effective) scale. Watch it here.
Weekend at Bernie’s is an idiotic idea for a film and pretty disturbing, so thankfully the Digital Shorts decided to point out its stupidity twenty years later! “Party at Mr. Bernard’s” is the realistic version of Weekend at Bernie’s, where the party immediately realizes that Mr. Bernard is dead, then the two party bros go on trial for parading around his body. Since Mr. Bernard is played by Robert De Niro, it means that he just has to sit there and let comedy happen around him, which is probably the best way for De Niro to do any form of comedy. Watch it here.
“Stumblin’” is such an unbelievably specific joke to make an entire short about, as it’s not exactly a parody of the song “9 to 5,” but rather a joke about the first line in “9 to 5,” which talks about tumbling out of bed and stumbling to the kitchen. But “Stumblin’” has Andy Samberg and later Paul Rudd just stumblin’ through their entire day. Every time Samberg and Rudd get together for a short, it’s wonderful and “Stumblin’” is somehow the only short written by Mike O’Brien. Maybe the biggest surprise in “Stumblin’” is that this might be the only thing in history not improved by Paul McCartney, who seems like a completely superfluous addition.
The Digital Shorts often knew how to utilize musicians in a way to make them hilarious, from Justin Timberlake to Adam Levine. But one of the more underrated examples is how they use The Jonas Brothers in “Property of the Queen,” as Andy discovers they’re an ‘80s hair band that discovered eternal life through a wizard. The Jonas Brothers completely sell the bit, going all-in with insane performances and brilliantly stupid songs with lyrics that prove they’re eternal. If the Jo Bros ever get back together (and I pray that they do), they should just tour as Property of the Queen.
Reminiscent of the “Old Glory Insurance” skit from the mid ‘90s, “Grandkids in the Movies” has an older man having his grandsons (Samberg & Hader) digitally inserted into films to help ease older viewers into the experience. For example, they let their grandfather know that a phone ringing during Michael Clayton is in the film, not his own phone, or just tell him to fast-forward through the awful convenience store scene in Juno. Considering how often SNL does fake commercials, it’s surprising that it took the Digital Shorts three years to do their first one and for it to be this great. Watch it here.
One of the better ideas to come out of Michael Phelps’s SNL episode is the strange “Space Olympics,” a short about a poorly planned attempt to take the sporting event into outer space. For a short, it takes “Space Olympics” a while to get going, but once we start seeing the degradation of the space Olympics, it’s off and running. Samberg is dressed almost like a character from “The Hunger Games” (which incidentally was first published that same week) as he sings about how the event is doomed, with no sunlight or sound, no air and all events pending or cancelled before aliens attack the spaceship. All Phelps has to do is stand there, probably for the best considering how the rest of that episode went.
“Roy Rules!” is an incredible use of a straight man as SNL writer Bryan Tucker plays Roy, Andy’s brother-in-law that he is far too obsessed with. While Andy’s increasing interest in Roy gets more extreme, claiming he wants to have sex with Roy—which would be a 24/7 69—the most hilarious part of “Roy Rules!” is the deadpan reactions from Tucker, who is just not having Andy’s song, but is too nice to dissuade him. Equally great is Jorma Taccone’s directing, with quick cuts at just the right moments and on the most ridiculous aspects of Roy’s bland life. Watch it here.
It’s sad to think there was a time when we didn’t realize just how hilarious Jon Hamm could be. “The Curse (Sergio)” is pretty strange, even by Digital Shorts standards, as a sweaty saxophone player named Sergio (Hamm) curses a rude businessman, played by Samberg. “The Curse (Sergio)” also has an insane amount of scale for a short, spanning several years and pretty much tells an entire horror movie worth of story in just a few minutes.
The Digital Shorts rarely ever attempt to comment on modern issues, but “Iran So Far” matches the weirdness of the shorts with a really fun comment on Mahmoud Ahmadinejad’s visit to New York City. “Iran So Far” works because of how completely straight it’s played, as Samberg samples Aphex Twin’s “Avril 14th,” while Adam Levine comes in with a chorus of children and Armisen as Ahmadinejad seems unaware that he’s in a song about gay love. As a nice little capper, Digital Short secret weapon Jake Gyllenhaal pops up at the end after Ahmadinejad is name dropped as looking like a hairy Gyllenhaal.
“Body Fuzion” is the only Digital Short written by a group of women, but with Amy Poehler, Maya Rudolph and Kristen Wiig, it features some of the funniest women in the show’s history. “Body Fuzion” doesn’t work when it goes for huge jokes, such as Drew Barrymore showing her flexibility by doing a standing split with a fake leg, but succeeds with the smaller details that make it feel like a real ‘80s aerobics tape. The “extremes” of the different difficulties—for high impact weight lifting, life one-pound weights, for low impact, lift air—seem both silly, yet also like they could’ve really been lifted from an actual workout tape. Based on their performances, it seems like Poehler, Rudolph and Wiig have watched their fair share of the real deal, and they go all in with what they’ve learned. Watch it here.
After the runaway success of “Lazy Sunday,” it surprisingly was over a month before the follow up “Young Chuck Norris.” The video takes a wonderfully strange idea—an ‘80s-inspired music video by a Chuck Norris enthusiast (Doug Brogar) singing of the younger days of his hero—then takes into some increasingly stranger ideas—Norris can’t quit punching everyone he comes in contact with and he loves digging through trash, apparently. “Young Chuck Norris” is a classic example of the Digital Shorts taking a great idea, but building and building onto it so many different layers that it’s like adding icing to an already fantastic cake. Watch it here.
It took a while for the Digital Shorts in season 36 to take off, but “Shy Ronnie 2: Ronnie and Clyde” brought about the first worthwhile one of the season by improving on one of their most famous shorts. “Shy Ronnie 2” is better than the original in every way: it’s a funnier, catchier song that gives both Rihanna and Ronnie better parts, the bank robbery setting makes way more sense than the school from the first one and the Ronnie verse at the end is actually pretty badass. Plus Jon Hamm! What more could you ask for?
With Samberg leaving at the end of season 37, the Digital Shorts knew they’d have to go through the greatest hits, which brings us to maybe the biggest “Laser Cats” yet. With the seventh installment, “Laser Cats 7” gets Steven Spielberg to direct and allows him to reference almost all of his films, much in the way James Cameron did in “Laser Cats 5.” Spielberg’s filmography is much more enjoyable to poke fun at, as the plot largely comes from E.T., Close Encounters of the Third Kind and Jurassic Park, which of course gives us the Jurassic Cat, and Spielberg himself is way more into the bit than Cameron was. But “Laser Cats 7” even gives us a conclusion to this series, as Nitro leaves earth on a spaceship packed with the world’s laser cats, which no longer shoot lasers out of their mouths. What better way to go out than getting Spielberg to film the seventh and final installment in the laser cats series. Watch it here.
This coked-out Disney musical has that great Digital Short combination of quick-succession jokes and the ability to literally go anywhere it wants. “Great Day” has a drugged Samberg singing with strangers, animated birds, freaking out when people touch him and believing he’s in The Matrix. Some of the best Digital Shorts embrace the surprise of having no idea where it’s going to head from one second to another and “Great Day” is a fine example of that craziness working at its best.
Have you been on a boat since “I’m On a Boat” premiered? Then odds are the song’s been ruined for you by people who think it’s funny to sing all the time. I know your pain. Despite that, “I’m On a Boat” chronologically is the first song from Incredibad that works on its own without a video, proven by the fact that this song actually went platinum and was nominated at the Grammy’s for Best Rap/Sung Collaboration. But even though every Lonely Island member makes an appearance in “Jizz In My Pants,” “I’m On a Boat” is the first to present them all in a short equally, with Akiva Schaffer getting just as much time as Samberg and Jorma Taccone playing the straight man who gets left on the shore. But to be fair, if you’re gonna go on a boat, who wouldn’t take T-Pain over Jorma?
The Lonely Island’s first video in two years, “YOLO” might also be their most ambitious song, in terms of their directing and song production. “YOLO” is one of their most beautiful looking shorts and for just three minutes, there’s an insane amount of locations and various stuff going on. But also, just look at that song. They’ve got Adam Levine (whose best work of his career is in these shorts), Kendrick Lamar on a guest verse and a brilliant sample of The Joy Formidable. As The Lonely Island’s first single for The Wack Album and that album’s best track, “YOLO” is also really funny, taking the term YOLO as a way to protect your only life by any means necessary.
No short has as many jokes per second as “Flags of the World,” a minute and a half burst of fantastic jokes, one after the other in quick succession. Co-writer and director Jonathan Krisel worked on Tim & Eric and “Flags of the World” absolutely feels like a riff on the Tim & Eric style, mixed with a rapid-fire attempt to cram as many jokes into the shorts as possible. The combination works with incredible success. Watch it here.
“Japanese Office” feels less like a Digital Short and more like the pre-recorded bits that air nowadays, yet that doesn’t make “Japanese Office” any less brilliant. This is likely due to the new blood in the Digital Short, as its written by John Lutz—who would only go on to write one other short—and Marika Sawyer—who puts in her sole short effort. As it turns out, Ricky Gervais stole his idea for The Office from Japan and we get to see that version, which also happens to star Steve Carell as the Japanese version of Michael Scott. The attention to detail here is what really sells “Japanese Office,” such as how slightly the things on Michael’s desk change or the little twists on Office bits we know like the stapler in Jell-O or Michael’s awkward jokes. Also the casting couldn’t be more perfect, with Bill Hader as Dwight, Jason Sudeikis as Jim, Kristen Wiig as Pam and a silent Kenan Thompson as Stanley. If that weren’t all great enough, Darrell Hammond’s commercial in the middle for a Japanese tampon is completely out of left field, as is Gervais’s appearance at the end to let us know this was all funny because it’s racist.
“The 100th Digital Short” is every bit as insane as one would expect to be, referencing the best and worst to come from this format in just 3 1/2 minutes. Like a gigantic mashup, we get Reba with Shy Ronnie, Julian Casablancas holding his boombox up while surrounded by laser cats, and Sergio grinding all up on everything. Throughout the song, Jorma and Andy keep talking about how they’re going to celebrate by blowing themselves and this very well could’ve felt like them doing just that. But it’s not the self-referential patting their own backs that doesn’t work here, it’s the elements that don’t fit in with the Digital Short’s history, such as Justin Bieber, Usher and Will Ferrell popping in to interrupt the short’s flow. During any other short, these additions could’ve been welcome, but by showing up during a celebration of shorts they were never a part of, it distracts from all the craziness going on around them.
In recent years, Pee-Wee Herman has popped up sporadically in a variety of comedy styles, always excelling in everything from cameos on Comedy Bang! Bang!, WWE specials and late-night shows. But the combination of Pee-Wee and Digital Shorts might be his best pop up yet, as him and Andy Samberg go out for a night of shots, hit Anderson Cooper with a chair, and then both world’s friends collide for an intervention. The short is a perfect combination of these strange worlds, a style clash that works so much better than would’ve been expected.
“Everyone’s A Critic” could very well be one of the darkest things to ever appear on SNL, as Paul Rudd and Andy Samberg paint each other naked, present the painting at an auction, and somehow then make everyone bleed from their face and commit horrific suicides. But the switch in tone, from a silly Titanic parody into a violent, blood-covered, suicide circle is so huge and disturbing, the shock can’t help but make a person laugh. Watch it here.
If “Between Two Ferns” has proven anything, it’s that Zach Galifianakis can be absolutely hilarious interviewing anyone. In “Zach Looks for a New Assistant”—only one of two shorts Galifianakis ever did—he interviews children to be his new assistant and the result is brilliant. The kids tell him his fart jokes aren’t funny, are confused by him using a stapler as a cell phone and educate him on Justin Bieber. While most hosts allow themselves to just be a part of whatever Digital Short the cast can come up with, Galifianakis takes it a step further and makes them his own more so than any other host, and makes them better for it.
Digital Shorts are inherently weird, but “Business Meeting” allows the insanity to take over, throwing crazier and crazier ideas out in an almost stream of consciousness way. “Business Meeting” has Rainn Wilson as a boss looking for ideas to help save the company money by calling on various people in the office. It starts off mostly normal, until he starts asking people like “Gigantic Turkey Sub,” “Captain Pajama Shark” and “Arcade Fire” to submit their ideas, most of which involve cutting human resources. Just when the idea can’t get wilder, Wilson receives a phone call—even though his phone is his hand—and the building blows up. “Business Meeting” fills itself with such stupidity, it can’t help but just build and build until there’s nowhere to go but blowing up the building that held all this stupidity in it. Watch it here.
Besides Justin Timberlake, Zach Galifianakis might have excelled with the Digital Shorts more than any other guest. Despite only doing two, his shorts stand out from the rest, distinctly his and not just the usual Digital Short with whatever host stopping by being added on. In “Zach Drops By the Set” simply has Galifianakis popping up on various NBC shows, sneaking up on Dr. Oz, noisily eating Werther’s Originals as 30 Rock tapes, or showing up on SNL thirty years ago as a bearded child. Zach barely has to do anything at all in “Zach Drops By the Set,” but everything he does in this short is completely hilarious. Watch it here.
Take the dark depravity of “Everyone’s A Critic,” put it into a “Yo Gabba Gabba!” parody and you’ll get the horrific hell of “The Tizzle Wizzle Show.” The change from a bright, happy (supposedly) children’s program into a pill-infused knife fight in the dark is so jarring that it’s a huge shock to the system. While “Everyone’s A Critic” had Paul Rudd and Andy Samberg accepting the terror they had cause, James Franco’s fear and questioning of what the hell is going on only makes the entire experience more frightening, yet somehow even more hilarious.
In what would become the Digital Short with the most installments, for good reason, “Laser Cats!” is just as phenomenal as Andy Samberg and Bill Hader believe it to be. As Admiral Spaceship and Nitro, the two fight bad guys with cats that shoot lasers out of their mouth in the greatest low-budget sci-fi epic of all time. Lorne Michaels’ appearance in the series is likely a sign of just how important the Digital Shorts were to the show’s success at the time, and with masterpieces like “Laser Cats!,” it’s easy to understand why. “Laser Cats!” is such a dumb idea, but the opportunity to make it as crappy and odd as possible makes it brilliant in nearly every way.
Any Lonely Island song that just had Michael Bolton in the background adding little comments would’ve been great—as he does during the first verse in “Jack Sparrow”—and is still quite funny. But when Bolton goes all out, singing about Pirates of the Caribbean and his obsession with “the jester of Tortuga,” “Jack Sparrow” becomes another weird combination of ideas for the band that mesh together beautifully. It’s crazy to think that Bolton was one of many artists considered for the song, but he’s the perfect fit and made him relevant again to an entire new audience.
The second monstrous Digital Short hit—and likely the most popular one—“Dick in a Box” might be the pinnacle of the Digital Short’s success. After a big lull in the Digital Shorts, “Dick in a Box” brought the shorts back into must-watch territory and the ridiculous song would even go on to win an Emmy for Outstanding Music and Lyrics—surely the first song to win an award about putting your junk in a Christmas present.
When watching “Dick in a Box,” it’s the only time I can remember the audience being so loud during a pre-recorded segment that it’s easy to miss aspects of the song. But what’s truly fascinating about “Dick in a Box” is the many layers this song has. It’s a Christmas song, a ‘90s R&B parody and a joke about bad gift giving. It’s hilariously egotistical, yet undercut by just how genuinely excited Maya Rudolph and Kristen Wiig seem to be by this poorly thought out present. And like almost all Lonely Island songs, it even works as a damn catchy song.
While “Lazy Sunday” introduced the Digital Short to the mainstream, “Dick in a Box” made it a cultural phenomenon. Made during Justin Timberlake’s second hosting gig, it immediately turned him into one of the most reliable and game hosts in SNL history. Watch any retrospective on the past decade of SNL and there’s a 100% chance you will hear Timberlake and Samberg listing off the steps to putting your dick in a box. Between “Lazy Sunday” and “Dick in a Box,” maybe no one did more for viral videos than The Lonely Island and SNL in the 2000s. Watch it here.
Of the 104 Digital Shorts, there is no one short more underrated than “Two Worlds Collide (Ft. Reba McEntire).” In this incredibly crude duet, “two of the world’s greatest,” Andy Samberg and Reba McEntire, sing about their newfound “relationship.” Over the span of just two minutes, this short unfolds beautifully. First, it presents that we’re supposed to believe Kenan Thompson as Reba, then reveals that, yes, this is in fact a homeless man that just found a wig in a dumpster. But “Two Worlds Collide” also plays to the Samberg idiocy that is prominent in many shorts, as he literally tells Samberg that he is clearly a man, which he just ignores. Plus Reba’s verse tells us the story of a person that says “ever since I came out my momma’s butt, I knew I was destined for greatness,” not just a fantastic line, but also a reference to one of Samberg’s earliest skits, where he played a butt baby. It’s a shame “Two Worlds Collide” was never on a proper Lonely Island release, only appearing as a bonus track on Turtleneck & Chain special editions, because this is by far one of their most brilliant songs ever. Watch it here.
Like most sequels, “Laser Cats 2” attempts to be bigger and better than the original, and somehow it’s one of the few sequels that improves on the original in every way. “Laser Cats 2” doubles down on the shitty production values, with terrible special effects, idiotic ideas sprinkled through—like future table-tennis—and tiny little details that enhance everything around it, like even more people in the background that have no idea what the hell Andy Samberg and Bill Hader are doing with all these cats. But the true star of “Laser Cats! 2” is new villain Dr. Scientist, played by a tin-foil covered Jake Gyllenhaal, that is having a ridiculous amount of fun as he dances around while wearing a fake, drawn on mustache and accidentally slipping and calling Samberg’s character Andy…miral Spaceship. Watch it here.
While Steve Martin and Scarlett Johannson had appeared in Digital Shorts prior to this, the “Natalie Raps” is the first Digital Short to play with the persona of the guest in a fitting, hilarious way. Amazingly, “Natalie Raps” actually turns Natalie Portman into a complete badass, complete with an Andy Samberg hype-man dressed like Flavor Flav. But like many of the Digital Shorts that feature an original song, “Natalie Raps” is just a great song, and Portman sells every line perfectly, to the point that you almost believe she’d sit right down on your face and take a shit.
This might be a controversial opinion, but “Motherlover” is just a better written, catchier song than “Dick in a Box.” “Motherlover” goes completely in for these two guy’s delusions, while getting even creepier with their gift-giving ideas. Yet even though this should be a bad idea, the addition of Patricia Clarkson and Susan Sarandon as the mothers—who seem completely into the idea—makes the concept so much more hilarious. But “Motherlover”’s lyrics are even more imaginative and fun than “Dick in a Box,” and that chorus could’ve easily made this song a hit if it wasn’t for, you know, being about sleeping with your best friend’s mom. This isn’t actually the second best idea they’ve ever had, it’s the best one.
With only its second installment, the Digital Shorts became a monstrous hit with “Lazy Sunday,” as Chris Parnell and Andy Samberg rap about such mundane topics as cupcakes and being taken to dream worlds of magic. “Lazy Sunday” became an instant hit and one of the first viral videos—with some even crediting it for the boom in YouTube’s popularity and revitalizing Saturday Night Live for a younger audience.
“Lazy Sunday” also presents The Lonely Island for the first time on SNL, with Samberg in his first year as a performer on the show, while Akiva Schaffer and Jorma Taccone had only been on the writing staff for a few months. With “Lazy Sunday,” these three wrote, directed and edited their own material in a matter of a few days, launching them into massive success outside of the typical SNL format.
But simply put, “Lazy Sunday” is just an excellent song that immediately placed The Lonely Island in the pantheon of great comedy musicians. “Lazy Sunday” has The Lonely Island creating a fantastic song that just happens to be hilarious, working as both excellent musicians and excellent comedians. From almost the beginning, The Lonely Island perfected this new format and set the bar incredibly high for themselves going forward.
Ross Bonaime is a D.C.-based freelance writer and regular contributor to Paste. You can follow him on Twitter and you can find more of his writing at RossBonaime.com