Every Smiling Friends Episode, Ranked

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Every <i>Smiling Friends</i> Episode, Ranked

Every second of Adult Swim’s Smiling Friends is pure and utter glee. Created by Michael Cusack and Zach Hadel, the adult animated series (mostly) follows the adventures of Smiling Friends employees Pim (Cusack) and Charlie (Hadel) as they work to make the people around them smile. It’s a gloriously simple premise, but it’s this uncomplicated nature that provides Smiling Friends with such a vast space to continuously subvert fans expectations about what unpredictable adventure will come next.

The show was renewed for a Season 2 earlier this year, though there has not yet been news about an upcoming release date. Nevertheless, the beauty of Smiling Friends is in its quality of bingability. Season 1 consists of nine short episodes, each only 13 minutes long and built to be watched over, and over, and over again. But this also raises an important question: which episode is the absolute best?

Now don’t get me wrong, I think each episode is hilarious in its own right, and writing this list genuinely felt like I was picking between my own children. Nevertheless, someone has to rise up to the responsibility, and I’ve taken it upon myself to properly rank every episode of Smiling Friends thus far.


9. “The Smiling Friends Go to Brazil!” (Season 1, Episode 9)


Last on the list ended up being the show’s most recent summer special. Released in August, “The Smiling Friends Go to Brazil!” strays from how the show is typically structured and instead spends the entire episode on an uncomfortably realistic dialogue about a proper vacation nightmare. The Smiling Friends have just landed in Brazil and are at the airport trying to figure out where their hotel is, only to find out that nobody has booked one (I don’t care what anyone says, it was definitely Alan’s fault). This episode ranks low comedically as the scenario winds up being more frustrating than entertaining. Even so, the funniest part of the special is the fact that there are virtually no jokes throughout its entirety, and it’s this complete diversion of expectations that makes Smiling Friends so masterful.

8. “Who Violently Murdered Simon S. Salty?” (Season 1, Episode 5)


In a classic whodunnit manner, Pim and Charlie visit fast food restaurant Salty’s for a bite to eat, only to discover that the founder has been killed! Finding themselves in the midst of a murder mystery, the Smiling Friends duo take it upon themselves to investigate the restaurant’s employees, which includes a variety of zany food mascots. While “Who Violently Murdered Simon S. Salty?” is chock full of funny bits and sequences, the episode doesn’t feel all that surprising or exciting, which is why it’s lower in the list.

7. “Silly Halloween Special” (Season 1, Episode 4)


Embracing the holiday special is key to a successful comedy series, and Smiling Friends clearly know the importance of leaning into the spooky spirit. During the company’s Halloween party, Mr. Boss (Marc M.) asks Pim to collect firewood for the bonfire, warning him not to go past the rickety bridge. Pim notices that there is better wood across the bridge and crosses anyways, only to find himself in an avalanche of danger as he’s chased by a 3D forest demon. “Silly Halloween Special” spends a bit too much time basking in Pim’s terror, though it makes up for the lack of plot with its distinctive animated additions. Plus, the slow build ends up being worth it, as the ending has one of the funniest jokes of the season.

6. “Mr. Frog” (Season 1, Episode 2)


After famous television star Mr. Frog is fired from his show for swallowing a TMZ reporter, Pim and Charlie set out to rehabilitate his image in hopes of saving his career. This turns out to be harder than expected, as Mr. Frog is violent and unruly. The episode takes a fairly standard approach in illustrating a typical Smiling Friends job, blending in a satire of celebrity cancel culture between the show’s silly gags. The highlight of the episode turns out to be Glep and his brief adventures as the new Mr. Frog, and since the show primarily focuses on Pim and Charlie, it’s nice to see other characters get some time in the spotlight.

5. “Shrimp’s Odyssey” (Season 1, Episode 3)


In “Shrimp’s Odyssey”, a heartbroken Shrimp (David Firth) calls the Smiling Friends for help after going through a rough breakup with his beloved Shrimpina. This time around, we see Pim and Charlie split up, as Pim is convinced he can win Shrimpina back while Charlie thinks he should move on. Of course, Pim finds himself in a doozy as he accidentally falls in love with Shrimpina, which puts him in a terribly conflicted situation. Since most of Smiling Friends sees Pim and Charlie working together, seeing the duo function in separate spaces provides deeper insight into their characters and allows them both to properly shine. Not to mention, “Shrimp’s Odyssey” sees the hilarious entrance of Smormu, the newest Smiling Friend, whose presence is absolutely necessary.

4. “Charlie Dies and Doesn’t Come Back” (Season 1, Episode 8)


Out of the entire series, this season finale is probably the most ridiculous yet (which is in itself a feat of its own). After a tree falls on him, Charlie—wait for it—dies, as per the title. He finds himself in Hell, only to find that it has (literally) frozen over because Satan is sad. Charlie, being the Smiling Friend that he is, somehow finds a way to strike up a deal with the devil, who promises that if he is able to make him smile, he can return back to his life on Earth. It’s such a goofy premise, and what makes the episode so great is the attention to such intricate details in building the atmosphere of hell. I mean, it only makes sense that hell would consist of such specific irritations such as glitchy food delivery service apps and—Ugh!—discord gaming.

3. “Frowning Friends” (Season 1, Episode 7)


You can’t have happiness without misery, and that’s just what the Frowning Friends capitalize on. In this episode, we see a new company move in right across the street from the Smiling Friends, threatening to steal all of their customers. Whereas Pim and Charlie are focused on making someone smile, their doppelgangers Grimm and Gnarly come crashing in to remind people just how miserable life is. This causes an immense amount of tension for Mr. Boss, who is driven into sheer madness by the business competition. “Frowning Friends” is a standout episode not just for its unique storyline, but also in its eclectic cast of guest characters that truly illuminate how weirdly unpredictable Smiling Friends is.

2. “Enchanted Forest” (Season 1, Episode 6)


“Enchanted Forest” is Smiling Friends at its wackiest, craziest, most glorious absurdity. The animation is stunning as it takes place in a beautifully detailed magic forest, where Pim and Charlie are tasked with helping a princess smile for her portrait. Along the way, they befriend Mip, a small Hobbit-like man who accompanies them on their travels. As the trio embark on their journey, they find themselves experiencing a series of epic quests, all of which declare Charlie as a hero while Pim’s jealousy slowly turns him into an evil madman. “Enchanted Forest” cleverly builds a conflict between the two lead characters, giving us a chance to get to know Pim and Charlie beyond their jobs. When every episode is centered around fixing the issues of others, it’s gratifying to see the Smiling Friends work out some of their own.

1. “Desmond’s Big Day Out” (Season 1, Episode 1)


Coming in first is the show’s pilot episode, which showcases Pim and Charlie out on a typical Smiling Friends job. The duo visit Desmond (Mike Stoklasa), a suicidal character who spends the entire episode holding a gun to his head. Over the course of the episode, Pim is determined to convince Desmond that life is worth living, excitedly taking him around town in hopes of finding him a reason to smile. Meanwhile, Alan is convinced there’s a mouse in the office stealing his cheese, only to discover an infestation of “bliblies” are terrorizing the space. “Desmond’s Big Day Out” is easily the season’s funniest episode as it easily captures the absurd mundanity that Smiling Friends thrives on. Moments of colorful chaos are juxtaposed with the most ordinary dialogue, making it the perfect introduction to the series.

Dianna Shen is an entertainment writer based in New York. When she’s not crying over a rom-com, she can be found on Twitter @ddiannashen.

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