The 2020s has been another golden age for animated TV. Especially where more mature programming on Adult Swim is concerned. The crown jew of Cartoon Network’s late night adult time slot this decade has been Smiling Friends. Created by Zach Hadel and Michael Cusack, the wacky series just ended its three-season run earlier this month. The show itself follows the Smiling Friends organization run by Mr. Boss, and his employees Charlie, Pim, Allan and Glep, on a never-ending quest to make people smile.
That premise ends up transcending Smiling Friends as its audience rapidly grew from episode-to-episode. In its 27 episodes, there are too many masterfully funny, insane and great adventures to count. Creepy tales like “The Mole Man” and “Erm, the Boss Finds Love?” are just a few examples of Smiling Friends’ ungodly creative whim.
Scariest Analog Horror Series
These analog horror series are the most frightening shows the genre has to offer.
10
“Mr. Frog”
(Season 1, Episode 2)
Mr. Frog has undoubtedly become the most beloved guest character on Smiling Friends. For good reason too. This failed TV star turned failed US President came with a lot of clever community for our insane modern world. The Smiling Friends trying to help this deeply flawed and controversial figure is the first major test for our duo in the series.
Their trials and tribulations trying to reform Mr. Frog as he actively eats and assaults people set Smiling Friends’ comedy bar so high. “Hello, I’m Mr. Frog” is a line that fans subconsciously hear every time they see an image of this bumbling amphibian.
9
“Charlie Dies and Doesn’t Come Back”
(Season 1, Episode 8)
This episode was an early example of just how random Smiling Friends was willing to go. After Charlie dies, he’s sworn to hell. He has to make his journey to Satan to make a bargain. That’s easier than it sounds and just as humorous as it sounds. Charlie always threaded the line between a lovable guy and a miserable friend to Pim’s optimistic joy.
Charlie’s journey to hell gives us all that with some of the character’s most memorable moments. This includes his interaction with Satan himself, who turns out to be a burnt out gaming bro. We also get a funny moment from Mr. Boss, who does Charlie’s eulogy at his funeral. Of course, that quickly became a meme.
8
“Charlie, Pim, and Bill vs. The Alien”
(Season 2, Episode 5)
This Season 2 episode takes Pim and Charlie out of the office in an effort for the former to bond more with his best friend/co-worker. This leads them to Pim’s friend group, who are avid UFO watchers. Charlie doesn’t believe in that extraterrestrial mumbo jumbo. That is until they get abducted by aliens themselves. What follows is a thrilling homage to the sci-fi horror genre as Charlie and Pim try their best not to get probed.
Smiling Friends‘ wacky humor style blends so well with this larger-than-life genre. Like the best episodes on the list, the icing on the twist is the punchline of the twist. There’s more to Pim and Charlie’s abductors than meets the eye. Their reaction to what they discover is simply comedy gold. Particularly when they find out the Earth is actually flat.
7
“The Curse of the Green Halloween Witch”
(Season 3, Episode 4)
This is by far Smiling Friends‘ craziest episode. “The Curse of the Green Halloween Witch” is a complete love-letter to the horror genre. The show has had many plotlines and Easter eggs tied to this blood-soaked genre throughout its run, but this pulls the entire rug out from under our favorite Smile Friends. A Green Witch puts a curse on the company after they didn’t give her money. Body horror, homages to franchises like Silent Hill and visual insanity ensue.
It’s scary for even the most seasoned horror fan. Hadel and Cusack pushed the envelope, burnt it and resurrected it in killer fashion. There’s very little humor in these 10 minutes, but it never lost what made Smiling Friends a household name in the first place. The ending does give this Wizard of Oz dream-like explanation that’ll make you release all your sweat-filled tension and have you giggling like an idiot. However, that doesn’t change the unique scars this episode left on its viewers.
6
“Gwimbly: Definitive Remastered Enhanced Extended Edition DX 4K (Anniversary Director’s Cut)”
(Season 2, Episode 1)
This episode is just as absurd as its extremely long title sounds. The Season 2 premiere is a love-letter and humorous retrospective of the rise and current fall of the video game industry. At the center of that is Gwimbly who’s our Super Mario and Rayman-like platforming mascot who was lost to time. He’s outdated, curd and very inappropriate at times, which made him the perfect person for the Smiling Friends to help.
Gwimbly was also unique given the fact that he was in a different art style from the rest of our main characters. Smiling Friends is at its best when it creatively blends together different animation techniques. Gwimbly being this 3D pixelated design monstrosity drives this crazy episode, and moments like Allen hosing him down with “Dirty Brown Water” are memorable to say the least.
5
“An Allan Adventure”
(Season 2, Episode 3)
Allan is arguably the best/most beloved character on Smiling Friends. He’s always a part of the best moments, Cusack’s voice is just laugh-out-loud funny. He’s the most relatable character since Squidward on SpongeBob SquarePants. That’s part of the reason why Allan’s only solo episode is on this list. His quest to find paper clips is an epic odyssey.
From getting into a fight with a spider in an office supply store to Allan crash landing on a deserted island, “An Allan Adventure” shows how desiccated this often third-wheel is to his friends and co-workers. The ending twist and Allan’s “reward” from Mr. Boss is the snickering icing on this episode. Especially when considering Allan’s brutally honest reaction to his employer giving him a mini-figure of Mr. Boss. “Um… I don’t really want this.”
4
“Silly Samuel”
(Season 3, Episode 1)
The season premiere of what would become the final season, “Silly Samuel” main storyline isn’t the reason it’s on this list. The sub-plot featuring Mr. Boss and Allan dodging the building inspector is why this instantly became one of Smiling Friends‘ top tier episodes. Mr. Boss has always been a beloved and mysterious character, but this episode gave us a rare glimpse into the head-honcho’s origins. Of course, he didn’t construct the Smiling Friends building legally.
That provides some of Mr. Boss’ best lines. “Allan, we are so f***ed” and “Do you realize, do you realize” became memes quickly. Also, the ending, which features the building inspector befriending them before disintegrating into thin air, is just too funny to put into writing. “Yo guys, it’s me Charlie… Hey did that guy just turn into sand?” will forever be iconic.
3
“Pim and Charlie Save Mother Nature”
(Season 3, Episode 5)
Similar to “Silly Samuel”, this middle episode of the third season is all about Mr. Boss and Allan. The latter overworked office manager is still doing his job on a company retreat at Mr. Boss’ cabin in the woods. The Smiling Friends finally have a vacation after a failed attempt a couple of seasons ago (more on that later), but no one can get through to Allan. Pim and Charlie go off on their own hilarious adventure, so Mr. Boss tries to get Allan in the vacation mood with some cookies.
This is where the episode completely goes off the rails. Allan loves the cookies so much. This is to the point that he’s eating them off Boss’ chest. It’s one of Smiling Friends’ most explicitly charged scenes and the randomness of it all makes it all the more gut-busting. Allan never showed any romantic interest in his employer before or after this episode. Yet, “Pim and Charlie Save Mother Nature” shows us a power couple fans never knew they needed.
2
“Enchanted Forest”
(Season 1, Episode 6)
The “Enchanted Forest” is on this list for a similar reason to “Pim and Charlie Save Mother Nature”. This episode starts off as a fantasy adventure parody of films like Lord of the Rings and games like Super Mario and Skyrim, with a bunch of hilarious side quests to boot. Pim and Charlie have to help a local princess smile as she has a stalker problem. They thus go on an epic quest for her. That leads them to Mip, a local eager to aid them.
The reason this episode is so high on this list is because the foreplay between Charlie and Mip is so out of left field. It’ll make anyone die of laughter. That’s especially true when you compare it to the mental breakdown Pim is currently going through due to their lack of progress in the adventure. It’s made all the more funny once the twist involving Mip in the episode is revealed.
1
“The Smiling Friends Go to Brazil”
(Season 1, Episode 9)
The Season 1 finale might go under the radar for most fans of the show. Yet, “Smiling Friends Go to Brazil” is a master class in a different kind of humor style. One of a very passive-aggressive nature. The plot sees Pim, Charlie, Allan and Glep go on vacation to Brazil. The only problem was that no one remembered to book the hotel. That means they’re stuck at the airport. Not even Mr. Boss can help them. What follows is 10 hilarious minutes of the group being cordial, but everyone is clearly upset.
Anyone who has a big friend group can relate to this. When your friend does something stupid, but you love them too much to blow up at them. The Smiling Friends never yell at each other once in this episode. It’s just awkward dead air, airport shenanigans, clear extra effort to be nice and the zany chemistry of our main leads this ship as they wait for a plan back home. That subtle comedy might not be everyone’s cup of tea, but it does make this Smiling Friends‘ best episode.
- Release Date
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2020 – 2026-00-00
- Network
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Adult Swim
- Directors
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Zach Hadel, Michael Cusack, Jeff Liu
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Michael Cusack
Pim Pimling / Allan Red (voice)
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Zach Hadel
Charlie Dompler / Glep (voice)
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Joshua Tomar
Armless Boss (voice)