Smiling Friends is the newest animated comedy from Adult Swim. Created by Michael Cusack and Zach Hadel, Smiling Friends follows Charlie and Pim, employees at Smiling Friends Inc., as they work to spread happiness to the world. The pilot episode aired on April 1, 2020, and after nearly two years of anticipation, the first season has finally been released. With all eight episodes of Season 1 available on Adult Swim’s website, it’s time to count down the best of the Smiling Friend’s adventures so far.

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8. Silly Halloween Special (Season 1, Episode 4)

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It’s Halloween time, and everyone at Smiling Friends Inc. is dressed up and ready to celebrate. Well… almost everyone. Charlie (Zach Hadel) refuses to dress up for the company Halloween party out of fear that any costume he wears may one day be considered offensive. On the other hand, the cheerful and optimistic Pim (Michael Cusack) can’t wait to begin the celebration. Mr. Boss notes Pim’s enthusiasm and asks him to collect firewood for the bonfire but warns of danger past the rickety bridge. Pim sets out to collect the wood but crosses the bridge despite Mr. Boss’ warning. Suddenly, he finds himself lost and hunted by a forest demon. Pim desperately makes his way back into the office, but the demon is still in pursuit. After bursting into the Halloween party after Pim, the demon is met with some extremely offended guests who believe he’s dressed up in blackface. A mob forms and the forest demon is ripped apart, eaten, and burned for the Halloween bonfire. All’s well that ends well.

This episode sticks to the typical Smiling Friends format of satirizing modern culture with bizarre and over-the-top scenarios. In this case, they satirize “cancel culture” and the debate over what Halloween costumes are acceptable to wear. “Silly Halloween Special” also highlights the show’s iconic blend of artistic mediums. The forest demon is a 3D model in the otherwise 2D animated world. This gives the demon a distinct and otherworldly appearance that adds to the horror theme of the episode. Live-action footage is also used, as a strange old man introduces the audience to the story and reflects on it afterward. “Silly Halloween Special” is fun overall, but the episode’s focus on Pim being chased doesn’t leave as much room for comedic moments. For that reason, it’s placed last.

7. Who Violently Murdered Simon S. Salty? (Season 1, Episode 5)

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Charlie and Pim are looking for a quick meal at Salty’s but find that the restaurant’s founder, Simon S. Salty, has been murdered. Now it’s up to the Smiling Friends to find out which of the Salty’s mascots is the killer. After interrogating all the suspects, Charlie and Pim find a secret room where an old rejected mascot is chained up. He gives the pair security camera footage to aid in their investigation and then passes away in Pim’s arms. After reviewing the tape, it turns out all the mascots tried to kill Salty, but not before he died of a heart attack. Believing they’ve been acquitted of any wrongdoing the mascots flee the scene and begin terrorizing the town.

In this episode, Charlie and Pim’s interactions with the mascots provide plenty of laughs, and the murder mystery makes for a unique Smiling Friend’s story. Perceptive fans can also find some small easter eggs hidden in this episode. Drawings from Cusack and Hadel’s The Very Positive Stream are used for movie posters in the background.

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

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It’s Christmas and like all good friends, Charlie and Pim are spending the holidays arguing. The pair get in a fight about Charlie’s apathetic attitude while searching for a Christmas tree in the woods. Charlie insists on cutting down the tree as a sarcastic response to Pim’s comments but ends up dying as the tree falls on him. Charlie wakes up in Hell only to find that it has literally frozen over because Satan is down in the dumps. That sounds like a job for a Smiling Friend! After venturing through Hell, Charlie finds that Satan has become a vaping, junk food-addicted gamer. The two strike a deal for Charlie to get his life back if he can cheer Satan up. But after criticizing Satan’s poor lifestyle, Charlie ends up getting tortured, much to Satan’s enjoyment. With Satan cheered up, Charlie upheld his part of the deal, and God (Gilbert Gottfried) sends him back to Earth.

“Charlie Dies and Doesn’t Come Back” has perhaps the funniest premise of the episodes in Season 1. Satan’s 3D model looks amazing, Gilbert Gottfried’s performance as God is hysterical, and the satire of lazy, dopamine-addicted people is spot on. Overall, this episode was a great conclusion to Smiling Friends’ first season.

5. Enchanted Forest (Season 1, Episode 6)

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In this episode, Charlie and Pim are tasked with making the Princess of the Enchanted Forest smile. On the way, they meet Mip, a forest folk who looks suspiciously like Bilbo Baggins from the 1977 animated adaptation of The Hobbit. Mip is on a quest to deliver a present to the Princess, so the trio agrees to travel together. During their travels, Charlie finds himself declared a hero and Pim’s jealousy gets out of control. The two fight and Mip is accidentally killed in the process. With his dying breath, Mip asks Pim to finish his quest and deliver the gift to the princess. However, when the princess hears about Mip, she tells the Smiling Friends that he is a stalker. Mip’s present is revealed to be a bomb that nearly kills the princess when she opens it. Charlie and Pim assure the Princess that Mip is dead, and she can finally relax and smile. Another job well done!

Successfully blending the Björk stalker and The Hobbit into a hilarious episode is a great example of how talented, creative, and off-the-wall the Smiling Friend’s team is.

4. Mr. Frog (Season 1, Episode 2)

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After beloved TV icon Mr. Frog is canceled, Charlie and Pim set out to save his career. Meanwhile, their coworker Glep is hired as Mr. Frog’s replacement. All attempts at rebuilding Mr. Frog’s public image go disastrously. He strangles fans, maims charity workers, and botches an appearance on The Tonight Show so badly he gets completely de-platformed. Things aren’t going well for Glep either. The executive producer for The Mr. Frog Show insists on sanitizing Glep’s personality into something bland, safe, and “un-toxic”. The episode concludes with Mr. Frog storming onto the show’s set, apologizing on live TV, and eating the executive producer. This clip goes viral, and Mr. Frog becomes richer and more famous than ever before.

“Mr. Frog” is a fairly standard episode of Smiling Friends, narratively, but it’s one of the funniest. Glep getting some attention was also appreciated, as most episodes of Season 1 focus solely on Charlie and Pim.

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

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In “Shrimp’s Odyssey”, the Smiling Friends get a call from a depressed shrimp who’s going through a rough breakup. Charlie thinks Shrimp should move on and focus on improving himself before finding another woman. But Pim wants to set Shrimp and his ex up on a blind date to get them back together. The two agree to split up and try both plans. Charlie takes Shrimp around town to get new clothes, a tan, and hit the gym. While this is happening, we get potentially the most hilarious scene in the entire show. After coming out of a dressing room, Shrimp is illustrated in a hyper-realistic art style wearing what Charlie describes as a “don’t come to school tomorrow” outfit. While this is going on, Pim finds Shrimp’s ex-girlfriend Shrimpina but falls in love with her himself. In the end, Pim decides to do the right thing and sets Shrimpina and Shrimp up for dinner. But Pim got the wrong girl! “Shrimpina” turns out to be a woman named Jennifer. Shrimp and Jennifer really hit it off though, and the job is a success after all.

“Shrimp’s Odyssey” is full of hilarious scenes and easter eggs for fans, like the voice cameo by Youtuber “Chills”. The episode also introduces Smormu, the newest Smiling Friend, who becomes a very important character..

2. Frowning Friends (Season 1, Episode 7)

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A rival company just opened across the street from Smiling Friends and is threatening to put them out of business. The new company, Frowning Friends, works to spread misery to anyone trying to improve their lives, and they’re shockingly good at it. No matter what the Smiling Friends try, the Frowning Friends have them beaten. The stress of business competition makes Mr. Boss go insane and try to kill the Frowning Friends while they’re giving a speech about how nothing matters. When confronted with the assassination attempt, the Frowning Friends drop their nihilism and one of them begs for his life. Mr. Boss calms down and comforts them, but they end up getting killed by angry “Renaissance Men” anyway.

“Frowning Friends” is a great satire of people who try to tear down anyone attempting to improve themselves, and guest appearances by Warren Buffet, Mr. Peanut, and Ronald Reagan make this episode unforgettable.

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

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We end our list where the season started, episode 1, “Desmond’s Big Day Out”. This episode proves that they hit a homerun on their first try. The Smiling Friends get a call from a concerned mother who needs someone to help her son, Desmond. Turns out, her son is dangerously suicidal and constantly holds a gun against his head. Pim does everything he can to bring happiness to Desmond but fails and falls into depression himself. While Charlie and Pim are out on the job, their coworker Alan is trying to deal with a severe infestation of “bliblies”. Desmond and the Smiling Friends return to the office and find Alan being crucified by the bliblies. Desmond shoots one of the creatures in self-defense and realizes that pest control is his passion. His depression is cured, but Pim’s isn’t.

This episode is hysterical and has countless moments that have already become iconic, like the rotoscoped man and Pim’s depression face. “Desmond’s Day Out” is what first captivated audiences and it’s easy to see why. It’s the funniest episode of the show yet. Overall, Smiling Friends had a great first season, and it’s definitely worth a watch for fans of irreverent and bizarre cartoons. Here’s hoping Season 2 is on its way!