10 Best Smiling Friends Episodes

Smiling Friends is one of the funniest, most inventive, most daring TV comedies to come along in the past decade. It’s a crying shame that creators Zach Hadel and Michael Cusack have decided to end the show after three seasons, but at least it went out on a high note. I’d rather Smiling Friends not go on for long enough than go on for too long. Every TV show eventually becomes hit-and-miss and yields diminishing returns. Smiling Friends probably had another couple of good seasons in it before that downturn, but as it stands, the series is practically perfect.

There are no bad episodes of Smiling Friends, which is not something you can say about most TV shows. There are just 27 episodes of Smiling Friends, and they’re all only 10 to 11 minutes long, so the series is a nice, breezy binge-watch. (I watched the entire thing in the space of 24 hours.) But, while there are no bad episodes, there are some standouts, like “Shrimp’s Odyssey” and “A Allan Adventure.” So, here are the greatest episodes from Smiling Friends’ criminally short run.

10

Desmond’s Big Day Out

Season 1, Episode 1

It’s extremely rare that a TV show finds its feet and settles on a voice and a tone in the very first episode; normally, it takes a few weeks to figure it out. But the pilot episode of Smiling Friends is a perfect introduction to the series. The show would go on to experiment with lots of different narrative devices, but it started off with a typical day in the lives of the Smiling Friends, with Pim and Charlie out on a typical Smiling Friends assignment.

The show nailed its pitch-perfect balance between the wonderfully zany and the unexpectedly shocking from the very beginning. The sheer shock value of having a character hold a gun to his own head for the entire episode was enough to put Smiling Friends on the map right out of the gate.

9

Gwimbly: Definitive Remastered Enhanced Extended Edition DX 4K (Anniversary Director’s Cut)

Season 2, Episode 1

Smiling Friends came back for its second season with one of its darkest (and best) episodes. The A-story of “Gwimbly” explores a new character dynamic between Pim and Allan, brilliantly juxtaposing Pim’s eternal optimism with Allan’s bitter cynicism, and the B-plot puts Charlie through a series of humiliating scenarios to put a smile on a violent intruder’s face.

The season 2 premiere reintroduced audiences to the uniquely offbeat tone of the series, but also promised an even wider and wilder range of animation styles. The show successfully avoided the sophomore slump with the meta multimedia mayhem of adding a retired video game character to the cast.

8

Frowning Friends

Season 1, Episode 7

When comedic characters are established, it can be fun to introduce their polar opposites, like Seinfeld did with the “Bizarro Jerry” episode and Futurama did with the parallel-universe episode. In Smiling Friends’ seventh episode, a rival business moves in next door, doing the exact opposite of what the Smiling Friends do.

The Frowning Friends are evil versions of Pim and Charlie and Allan, who spread hatred and negativity and pessimism. Smiling Friends promotes an optimistic outlook on life, and the power of a positive attitude, and “Frowning Friends” is a surprisingly poignant critique of overly negative people who spread hate and cynicism.

7

Mr. President

Season 2, Episode 2

It’s been tricky to do political satire in the past few years, but Smiling Friends nailed it with the season 2 episode “Mr. President.” Having a miserable, unpopular President of the United States call the Smiling Friends in distress was an ingenious setup to satirize the institution of government, and the downside of putting power in the hands of elected officials.

Jimble, played spectacularly by Mike Bocchetti, isn’t a clear avatar of either candidate. The episode walks a bipartisan line by lampooning the general ineptness and unpopularity of politicians on both sides.

6

A Silly Halloween Special

Season 1, Episode 4

The fourth episode of Smiling Friends might call itself “A Silly Halloween Special,” but it’s a darn sight more terrifying than most of the other Halloween specials that air over the holiday season. Like Shaun of the Dead, Widow’s Bay, and An American Werewolf in London, it succeeds at being both funny and frightening at the same time.

Pim’s journey “beyond the rickety bridge” is visually stunning, and the first appearance of the demon by the lake is truly unsettling (but the chase that follows is a great slapstick gag). To top it off, this episode has a hilarious live-action framing device with a Robert Stack-type host introducing the horror.

5

Silly Samuel

Season 3, Episode 1

The season 3 premiere “Silly Samuel” is bolstered by a series-best guest performance by Conner O’Malley. He’s so good at playing the comedy of rage, as we’ve seen in countless Tim Robinson sketches, and the role of the deeply insecure, deeply angry Silly Samuel gave him plenty of opportunities to play into that.

The only downside to the episode is that there isn’t much attention given to Pim and Charlie. It’s more about catching us up on where they are now than just being a typical episode.

4

Who Violently Murdered Simon S. Salty?

Season 1, Episode 5

“Who Violently Murdered Simon S. Salty?” is essentially Smiling Friends meets Knives Out. Pim and Charlie are tasked with solving the murder of Simon S. Salty, the founder of Charlie’s favorite greasy-spoon fast-food joint, Salty’s, where the staff are rude, the floors are dirty, and the food is toxic.

It’s a hilarious subversion of the usual whodunit formula, specifically flipping Murder on the Orient Express’ everyone-dunit twist on its head. The twist ending of Smiling Friends’ murder mystery episode is both delightfully absurd and genuinely surprising.

3

Erm, The Boss Finds Love?

Season 2, Episode 4

When Mr. Boss gets married, Pim and Charlie grow concerned that his wife has ulterior motives. It turns out she’s actually the daughter of Satan, who emerges from her demonic slumber every 100 years to kill men of great power and bring their belongings to her father.

“Erm, The Boss Finds Love?” starts off as a supernatural satire of the gold digger stereotype, but it morphs into one of the best Exorcist parodies ever made, and ends on a sweet note as Mr. Boss reaffirms his commitment to the Smiling Friends. It’s pretty impressive for an 11-minute episode.

2

A Allan Adventure

Season 2, Episode 3

It’s always a big risk when a TV show shifts away from its main characters and gives a spotlight to a supporting character. Sometimes, they can divide a fan base, like Ted Lasso’s “Beard After Hours” episode. Other times, they can be outright disappointing, like that one Mandalorian episode with the cloning engineer on Coruscant.

But, every now and then, an experiment like that yields one of the series’ best episodes, like The Last of Us’ “Long, Long Time” or Mythic Quest’s flashback episodes or, indeed, Smiling Friends’ Allan-centric episode. This episode has a delightfully zany sensibility, and it was fascinating to learn more about this side character.

1

Shrimp’s Odyssey

Season 1, Episode 3

This is the episode that made me fall in love with Smiling Friends. I’d really enjoyed the show from the jump, but it became one of my all-time favorites when I saw David Firth’s portrayal of a “truly pathetic” shrimp yearning to be reunited with his ex-girlfriend Shrimpina.

The episode keeps Pim and Charlie separate for the most part, so it might not be the best Smiling Friends episode to show a new viewer. But pound for pound, laugh for laugh, this is the funniest episode the series ever produced.

Smiling Friends

Release Date

2020 – 2026-00-00

Network

Adult Swim

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  Michael Cusack

  Pim Pimling / Allan Red (voice)

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  Zach Hadel

  Charlie Dompler / Glep (voice)