Every Smiling Friends Episode, Ranked

TV Lists Smiling Friends
Every Smiling Friends Episode, Ranked

Every second of Adult Swim’s Smiling Friends is pure and utter glee. Created by Michael Cusack and Zach Hadel, the Adult Swim 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 beauty of Smiling Friends is in its quality of bingability. Each episode is less than 15 minutes long and designed 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. 


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

smiling-friends-episode-9.jpgLast on the list ends up being the show’s summer special, which premiered in August 2022. “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 Allan’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. 

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

smiling-friends-episode-5.pngIn 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.

15. “Brother’s Egg” (Season 2, Episode 5)

In “Brother’s Egg,” Pim and Charlie face an unusual challenge when called to assist aspiring mad scientist Daniel “Professor Psychotic” in his quest to create life by injecting his DNA into chicken eggs so he can take over the world. As Daniel is explaining his plan, his older brother Doug (Joel Haver) enters to complain about the noise and his lack of job prospects, ultimately deciding to evict Daniel from his apartment. Pim and Charlie attempt to reconcile the brothers, but their intervention goes awry when the brothers break out in a physical fight. Similar to “The Smiling Friends Go to Brazil,” “Brother’s Egg” dials back the number of jokes per minute and instead amplifies a feeling of discomfort, particularly present when watching the brothers argue. Haver’s guest animation on the episode proves to be the highlight, especially when Daniel switches into a rotoscoped version of himself while battling it out with Doug.

14. “Mr. President” (Season 2, Episode 2)

In “Mr. President,” Pim and Charlie find themselves tangled up in the messy world of politics after receiving a call from the wildly unpopular President Jimble (Mike Bocchetti). He’s desperate for the Smiling Friends’ help with his reelection bid against Mr. Frog, who is running a successful smear campaign against him. Jimble’s presidency spirals into complete madness as he struggles with embarrassing mishaps and disastrous policy decisions—from soiling himself during a speech to crashing the economy. The episode serves up political parody with a side of mixed media, animating real-life people like Jimble into the 2D Smiling Friends universe. And while it’s got the goofy return of the infamous Mr. Frog, the narrative at times feels like treading familiar ground from its Season 1 counterpart. Not a bad episode per se, but maybe not built to be repeat viewing. 

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

smiling-friends-episode-4.jpgEmbracing 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 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.

12. “Magical Red Jewel (aka Tyler Gets Fired)” (Season 2, Episode 7)

Perhaps the most exciting aspect about Season 2 has been how the show has managed to reinvent itself while still keeping the series’ core absurdity intact. In “Magical Red Jewel (aka Tyler Gets Fired),” Mr. Boss (Marc M.) asks Pim to accompany him to the foreign country of Spamtopia as his translator. Pim, having learned Spamish from his childhood pen pal Oscar, joins Mr. Boss on his quest to purchase a magical red jewel. Spamtopia bursts with vibrant, neon animation, featuring oddly-shaped buildings and surreal floating objects against a rainbow-gradient backdrop. The sole law in the country—avoid eye contact with residents under penalty of death—is broken when Pim accidentally locks eyes with “Mr. Jester,” the jewel seller who also reveals himself to be the ruler of Spamtopia. And to really highlight how wacky Spamtopia is, Mr. Jester is voiced by text-to-speech, specifically TruVoice Adult Male #1.

Back at Smiling Friends HQ, Mr. Boss leaves Charlie, Allan, and Glep to babysit his son, Jason. Unfortunately, Jason inexplicably dies soon after his dad’s departure, leaving the trio to navigate how to break the news. The episode, while somewhat lacking in terms of story, compensates with increasingly stimulating visuals, especially when Spamtopia descends into anarchy at the end, and is accompanied by chaotic static glitching and the word “goodbye” scattered across the screen.

11. “Pim Finally Turns Green” (Season 2, Episode 8)

It’s Christmas time in the Smiling Friends universe, and Charlie has built the world’s ugliest snowman. When Pim adds a daffodil to the snowman’s head, “Rotten the Snowman” inexplicably springs to life. Bewildered yet overjoyed with the revelation that he is now alive, Rotten and Pim enjoy a blissful montage frolicking around in the snow. It’s heartwarming to finally see a character finally match Pim’s boundless positivity. However, when Rotten requests to go to the beach, Pim warns him that he’ll melt in the sun—an idea that puzzles the snowman. As Pin explains the concept of mortality, Rotten goes into a state of complete panic, screaming for days on end. It’s then up to the Smiling Friends gang to try and convince Rotten that death isn’t as terrifying as it seems, and their efforts include a cameo from “Bill Nye the Science Guy” (voiced by Marc M.) who breaks out into song. And while the episode doesn’t reach the same outrageous heights as the Season 1 finale, “Pim Finally Turns Green” still manages to be a solid end to a great Season 2. 

10. “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.

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

smiling-friends-episode-3.jpgIn “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.

8. “Erm, the Boss Finds Love?” (Season 2, Episode 4)

Smiling Friends’ second take on the Halloween episode is an absolute delight, and it somehow manages to outshine its Season 1 predecessor by a landslide. In this episode, Mr. Boss marries Brittney (Erika Lindbeck), a deformed demon who rebrands the Smiling Friends office into “Brittney’s Beautiful Demonic Flowers.” Sensing something sinister going on, the gang discover that “Brittney” isn’t who she says she is, but actually Fillia Diabulus, the daughter of Satan who emerges every 100 years to kill men of great power and give their belongings to her father, and the only way to stop her is to drain her blood on a full moon. For an 11-minute runtime, “Erm, the Boss Finds Love?” is packed with so many impressive jumpscares and serves as a great parody of The Exorcist. The post-credits scene is one of the best of Season 2, but I’ll leave that for you to judge for yourself.

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

smiling-friends-episode-8.jpegOut of the entire series, the Season 1 finale has probably the most ridiculous storyline 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. 

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

smiling-friends-episode-7.jpgYou 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.

5. “Charlie, Pim, and Bill vs the Alien” (Season 2, Episode 6)

I honestly didn’t think it was possible for Smiling Friends to get any more ridiculous, and that’s a testament to the show’s writers. In this episode, Pim drags Charlie to his UFO sighting group. What starts as a dull meeting quickly spirals when Pim, Charlie, and poor Bill (Hans Van Harken) get abducted by aliens. As if that wasn’t enough, those aliens are in turn abducted by another alien race, who also happen to be throwing the ultimate cosmic party. Pim and Charlie find themselves as unwilling guests, while simultaneously seeking a way to escape and return to Earth (R.I.P to Bill, who immediately gets eaten after their initial abduction). “Charlie, Pim, and Bill vs the Alien” is truly Smiling Friends at its peak—creative concept, well-paced, and just delightfully weird. And, the payoff for the episode’s final joke is just too good to spoil.

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

smiling-friends-episode-6.jpg“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.

3. “A Allan Adventure” (Season 2, Episode 3)

Finally, an episode dedicated to Allan! Season 2 has been exciting with its blend of animation styles and exploration into characters beyond Pim and Charlie. “A Allan Adventure” takes us on the strangest journey yet: an impossible quest for paper clips. When Mr. Boss assigns Allan the seemingly simple task of buying more paper clips for the office, it turns into a series of wild escapades. From dodging thieves to helicopter chases with the Air Force, battling undead pirates, and facing off against a giant sea monster, Allan’s day gets crazier with every twist. “A Allan Adventure” not only delivers Smiling Friends’ trademark nonsense, it also gives us a deeper look into Allan’s world in the best possible way. Not to mention, watching this episode made me realize that I would love to watch a reimagining of every episode of Smiling Friends thus far, but from Allan’s perspective.

2. “Gwimbly: Definitive Remastered Enhanced Extended Edition DX 4K (Anniversary Director’s Cut)” (Season 2, Episode 1)

smiling friends

Two years between seasons is an eternity in TV land, but, luckily, Hadel and Cusack were able to make it well worth the wait. The Season 2 premiere sees the Smiling Friends back at it again, this time exploring a new partnership dynamic between Pim and Allan. Pim’s relentless optimism contrasts hilariously with Allan’s complete apathy, as the duo decide to help Gwimbly, a washed-up video game character who hasn’t been able to star in any new games because his parent company Insane Groundbreaking Games retains control over his I.P. They decide to try and crowdfund an independent Gwimbly game, only to find themselves under attack by the evil CEO and company mascot Troglor. The episode features nostalgic flashbacks to early PlayStation aesthetics, as seen in Gwimbly’s 3D character design as well as through clips of pixelated gameplay that feel as though they were taken straight out of the ‘90s. 

In another corner of the office, Charlie is left to his own devices to deal with James, a violent intruder that forces Charlie to do all kinds of degrading things to make him smile, including dressing like a ‘50s housemaid and baking him a casserole. This, of course, doesn’t work, and if the show wasn’t bizarre enough, the episode takes another turn when James casually rips Charlie’s entire nose off (the poor thing!). “Gwimbly” not only reintroduces the outlandish charm of Smiling Friends, but also sets the exciting tone for the season ahead, promising a mix of animation styles and even wilder storytelling.

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

smiling-friends-episode-1.jpegComing 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 man 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, Allan 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 show’s funniest episode as it 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.

For all the latest TV news, reviews, lists and features, follow @Paste_TV.

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