The 15 Worst Things the Always Sunny Gang Has Ever Done

Comedy Lists It's Always Sunny in Philadelphia
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The 15 Worst Things the <i>Always Sunny</i> Gang Has Ever Done

Tonight marks the the debut of It’s Always Sunny in Philadelphia season 15, and we can expect even more darkly comedic hijinks, shouting matches, and, perhaps, schemes and deeds that go a bit too far. The Gang is no stranger to the latter, so to mark 15 seasons of chaos, I am here to look back on 15 instances of them at some of their absolute worst.

This list touches on almost every season of the show’s record-breaking run. Some of these awful (but funny) acts were carried out by the Gang as a whole, some as individuals, and even with some teaming up against each other. At the end of the day, all five of them have done enough awful things to make them the worst people you love to love. Without further ado, prepare to visit the Gang at their most hilarious lows, just in time for season 15.

1. Terrorizing an Isreali Immigrant


Season 2, “The Gang Goes Jihad”

Every so often the Gang gets themselves into a position where they are doing something so sketchy it puts them in a position to question whether or not they’re being totally racist. In this early episode, they are told from a man recently immigrated from Israel that their bar is on his newly-bought property, and is making them move. Of course their response is to retaliate, but of course that takes them to horrible places, like dressing up as like Middle Eastern terrorists and making a threatening video, and eventually (if somewhat accidentally) burning down his whole building.


2. Getting Matthew Mara to Give Up the Priesthood


Season 2, “The Gang Exploits a Miracle”

While this season two episode may not ring the loudest bell off the cathedral that is your brain, it no doubt contains one of the worst things the Gang has certainly ever done, the effects of which reverberate across the series to this day. While exploiting a water stain in the Paddy’s Pub office that looks like the Virgin Mary they attempt to bring in one Father Matthew Mara (David Hornsby), a.k.a. Rickety Cricket, for a blessing. A devout priest who admittedly still has romantic feelings for Dee, the Gang makes the latter exploit those feelings to win him over. This includes making him believe she will be with him if he decides to leave the priesthood, which the poor man does at the end of the episode. Dee, of course, totally shuts him down, thus starting the odyssey of poverty and depravity of one Rickety Cricket.


3. Setting Dee on Fire…Twice


Season 3, “Frank Sets Sweet Dee on Fire”

In this episode, Frank, Charlie, and Mac are driven by their quest to become viral news sensations before the word “viral” was much of this thing. After missing Mac’s heroic moment saving a choking man, they look to re-create “heroic” moments by endangering the lives of others, namely Dee and some poor kittens. In not one, but two scenarios, the three of them decide to get Dee to try and save some cats, only to light her on fire in the process. Luckily they didn’t get to using their “cat chopping” apparatus, but still, setting cats on fire (and Dee, I guess) definitely ranks up there as some of their nastier ideas.


4. Kidnapping a Bar Critic


Season 4, “Paddy’s Pub: The Worst Bar in Philadelphia”

As entertainment writers know, it’s easy to ruffle some feathers. But it’s not often we are kidnapped and forced to write a new review. That’s exactly what the Gang did to a local critic (Fisher Stevens) who named their bar the “Worst in Philadelphia.” Across the episode they dive deeper into chaos in trying to figure out how to release him without him blabbing to the police, piling on one offense after another, including stealing his cat. It’s the Gang at some of their undoubtable worst, but fully illustrating how even when they’re being bad it’s okay because they’re also hilariously messy bitches.


5. Burning Down a Mexican Immigrant Family’s Home


Season 4, “The Gang Gets Extreme: Home Makeover”

Even when the Gang is trying to be at their best they’re likely to do some of their worst, and trying to do a real Home Makeover (if mostly to give themselves good karma) resulted in one of their worst acts of them all. Busting into the home of the Juarez family while playing death metal like lunatics, holding them prisoner and trying to make them “American”, and doing such a bad job actually renovating their home that they end up burning the whole thing to the ground. They ended up having to give the Juarez family their own family mansion in exchange, so I guess that counts as doing something good? Not really, but at least we know karma works.


6. The Whole D.E.N.N.I.S. System


Season 5, “The D.E.N.N.I.S. System”

Dennis is the one among the Gang who fits most neatly into textbook sociopathy – sort of a Patrick Bateman if he were white trash. So of course he would have a system for mentally manipulating women into sleeping with him, and thus he unveils The D.E.N.N.I.S. System to the group. Bad in that Dennis routinely deploys this on poor women, but made hysterical by the rest of the gang failing so bad at trying to do it themselves, this long-con kind of bad offers a glimpse into the Gang’s most twisted, even pathetic mind.


7. The (Fake) Baby Funeral


Season 7, “Sweet Dee Gets Audited”

Dee trying to scam the government for tax breaks by claiming the surrogate child she had as a dependant is pretty bad in of itself, but it’s the finale that really shows how far the Gang will go to cover their own asses. In order to get the IRS off Dee’s back the Gang holds a fake funeral for little Barnabus Reynolds, which even in the words of Dennis, is “the darkest thing they’ve ever done.” It’s grim and brilliant, and Frank going even further for the sake of realism by tossing a dead dog from the alley into the coffin is black comedy genius.


8. Pushing the Waitress to Her Breaking Point


Season 8, “Charlie and Dee Find Love”

Sure, Charlie getting a woman like Alexandra Daddario’s Rose is a stretch of the imagination, but sometimes you have to hope for the best. Dennis does not do this, in his twisted rationale believes the best way to “save” Charlie is to make the Waitress (Elizabeth Ellis) let him back into his life. Thus, he and Frank break into her house, poison her shampoo, and the latter even runs her down in his car, accidentally. Bloodied and in the hospital, she caves, and begs Charlie to come back (at a distance) to assist her. A cruel act on both Waitress and Charlie, but it does have a sweet ending.


9. Making Dee Hit Rock(ier) Bottom


Season 9, “The Gang Broke Dee”

When the Gang may have gone as far as they could to get back at one another, this episode pushed them to their most diabolical peak. Dee, having given up after years of verbal abuse and career failure, soon becomes a comedy superstar and finally is put on the path to success. But, in a tremendous twist, it’s unveiled it was all a ruse put on by Frank, Mac, and Charlie just to prove that Dee could, in fact, sink lower. Not as destructive or bluntly dark as some of their other worst moments, but as far as emotional destruction goes, that Gang has never reached a higher peak before or since.


10. Trapping People Inside A Burning Apartment


Season 9, “The Gang Squashes Their Beef”

In trying to move past some of their most classic beefs with recurring characters, the Gang goes and makes it all worse. In this Thanksgiving episode, the gang brings in contentious figures to try and make a fresh start, but because destruction often follows their best intentions, a fire breaks out in Mac and Dennis’ apartment. Instead of doing anything logical, the Gang barricades them all inside to get a “head start”. Maybe it would’ve been fine if everyone got out okay…but poor Cricket…


11. Taking All of Frank’s Blood


Season 10, “Frank Retires”

In this Game of Thrones-style episode, the Gang attempts to gain complete control of the bar. How they go about it is a mixture of classic Sunny hijinks, and partly horribly dangerous, at least when it comes to the Gang taking so much of Frank’s blood while he’s asleep that it nearly kills him. Rolling in on a scooter as pale as a ghost, it’s the closest we’ve gotten to DeVito returning as The Penguin from Batman Returns, but that’s not quite cool enough to justify the Gang nearly draining him of all life just to prove why they should get the office chair that smells like a thousand butts.


12. Starting a Cult


Season 10, “Ass Kickers United: Mac and Charlie Join a Cult”

Dennis starting a fake cult just to get Mac to stop eating his Thin Mints is, for this group, innocent enough to be charming, but what makes this among the worst they’ve ever been is in how far into it they go. Trying to be the best cult leader, it’s a battle between Frank, Dee, and Dennis for total mental control of Mac, Charlie, and supporting players, their methods ranging from disgusting to plain dangerous. Resulting in yet another fire and yet another death, it ranks near the top of the Gang’s most absurd, devious mental mind games.


13. Stealing Everyone’s Stuff/Torturing a Little Person


Season 11, “Charlie Catches a Leprechaun”

In a rather smart move to try and bring Paddy’s into the future, the Gang finds themselves digging themselves seven deeper into criminal territory. When Dennis’ plan for a bar-centric food truck experience goes wrong, he ends up stealing the wallets and phones of virtually every passenger, with he, Frank, and Dee leaving them all in the woods to walk back home. Oh, and then there’s Charlie going all Reservoir Dogs on a little person he believes to be a leprechaun. So, yeah, not their best St. Patrick’s Day. But at least Mac had fun.


14. Getting a Stripper to Grind in His Daughter’s Face


Season 12, “PTSDee”

In a previous entry I got into how the Gang got Dee to hit a true “rock bottom”, and here she gets a sort of revenge on the world by making one man hit his own in disgusting fashion. After being told by a male stripper that sleeping with her was his “rock bottom”, she pulls out the stops for a diabolical plan that ends with him unknowingly, heavily grinding his junk in the face of his already estranged daughter. All to prove she wasn’t his “rock bottom,” Dee effectively ruined two lives, and gave us all nightmares in the process.


15. Letting Frank Choke


Season 14, “The Gang Chokes”

The bond between the Gang isn’t exactly pure, but it speaks a lot about how they feel about each other-or at least just Frank-when they watch the man nearly choke to death in front of their eyes and do absolutely nothing. Perhaps as the title suggests, it was just a matter of shock, but the look on their faces definitely hints they simply didn’t care, and were maybe even a bit excited. Poor Frank; the man just wanted blue food!



Matt Rooney is an entertainment writer whose work has appeared in Collider, IGN, JoBlo, ScreenRant, and more. If you want to read more of his writing and musings, follow him@MrMattRooney on Twitter.

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