All Smiling Friends Episodes Ranked Worst To Best

It turns out making people happy isn’t always easy, as Charlie and Pim and the rest of the Smiling Friends often discover at their mortal peril. Their efforts always make me crack a grin though! Here are all episodes ranked worst to best.

17. Who Violently Murdered Simon S. Salty

This episode is the Smiling Friends take on the whodunit caper. Poor Simon S Salty was murdered most foul, and the gang has to figure out the identity of the culprit and bring a smile to the face of justice. While the interrogation sequences with fast food mascots are pretty clever, the gags in this episode don’t quite measure up to some of the more sophisticated entries on this list.

16. The Smiling Friends Go to Brazil

The Smiling Friends Go to Brazil is by far the most uncomfortable, squirm inducing episode of the series. Pleasant as a root canal. The Smiling Friends just landed in Brazil for vacation, but find themselves stranded in the airport after discovering no one booked a hotel. Despite the funny premise, it’s just a series of painfully real sounding arguments between co-workers. This episode is saved from the lowest slot on the list only by virtue of its sheer ballsiness – a comedy show episode where no jokes are told.

15. Mr. President

Smiling Friends had the chance to go for the political commentary gold but somehow missed the mark. The gang are recruited by the universally hated President Jimble, whose election opponent Mr. Frog is annihilating him in the polls. Rather than serving up savvy political satire, Smiling Friends resorts to whacky bathroom humor. It’s a fun episode for sure, but could have been far better.

14. Brother’s Egg

Another deeply uncomfortable episode, Brother’s Egg centers around the Smiling Friend’s newest client Daniel aka Professor Psychotic, whose master plan is to inject his DNA into chicken eggs and take over the world. The mad Professor’s older brother Doug comes home to find Daniel explaining his plan, which causes Doug to tear into him for being a failure. The eerily realistic dialogue makes this episode feel like a particularly tragic Jerry Springer clip. It’s just kind of a bummer.

13. Silly Halloween Special

Everyone loves a Halloween story! Except this episode doesn’t really have one. At the company Halloween party, Mr. Boss asks Pim to fetch some firewood but avoid going near the creepy bridge in the woods. Pim ignores Mr. Boss, and comes face to face with the freaky 3D animated forest demon. The rest of the episode is devoted to Pim being chased by the monster, which, while not serving up much in terms of plot, is easily one of the best animated sequences in the entire series.

12. Pim Finally Turns Green

Another holiday special! This Smiling Friends episode features the gang pulling a Frozen and building a snowman. But this particular snowman, christened as Rotten, doesn’t wanna sing. He wants to know why he’s alive and why he has to someday melt and die. The gang spend the rest of the episode trying to help the poor little guy manage his existential dread. A solid episode, featuring Bill Nye the Science Guy (along with his untimely death)

11. Magical Red Jewel (aka Tyler Gets Fired)

Magical Red Jewel is Smiling Friends in top form. Mr. Boss asks Pim to accompany him to the surreal neon world of Spamtopia to serve as his Spamish translator. There’s only one important law in the country, don’t look anyone in the eyes on penalty of death. Naturally, Pim breaks the rule in the first five minutes after crossing the border. The creative Spamtopian animation and the text-to-speech voice acting of its inhabitants make this episode one of the most creatively hilarious.

10. Shrimp’s Odyssey

Shrimp’s Odyssey is about a heartbroken shrimp (named Shrimp) who just broke up with his beloved Shrimpina. The Smiling Friends are gonna get her back for him! Well, half of them. Pim thinks that their romance can be salvaged, while Charlie advises the crustacean to move on with his love life. While seeing Pim and Charlie each get their own separate character arcs is a treat, the crown jewel of the episode is the introduction of Smormu, the newest (and best) Smiling Friend of all.

9. Mr. Frog

Mr. Frog is the latest victim of cancel culture… specifically for eating a TMZ reporter alive. The freaky man-frog hires the Smiling Friends as his PR managers to help him get back into the public’s good graces. The only problem is, Mr. Frog has no good graces himself. He’s combative, violent, and voraciously hungry. This episode is a hilarious critique of celebrity culture, and proof that you should never, ever meet your heroes.

8. Charlie Dies and Doesn’t Come Back

Spoiler alert: Charlie only does one of those things. After being fatally crushed by a fallen tree, Charlie awakens in Hell, which, as the adage goes, has indeed frozen over. Why? Satan is depressed, and doesn’t feel like feeding the fires of the inferno. If Charlie can make Lucifer crack a smile, he’ll bring the critter back to life. This season 1 finale is infernally fun.

7. Erm, the Boss Finds Love?

While Smiling Friend‘s first Halloween episode left more to be desired, they nailed it the second time around. Charlie and Pim’s beloved company is rebranded as Brittney’s Beautiful Demonic Flowers by Mr. Boss’s new demon girlfriend. Sensing that she’s in it for lesser reasons than love, the Smiling Friends discover that the demoness intends to drain Mr. Boss of his financial and bodily assets as a gift to Satan. Be warned, this episode is packed to the brim with brilliant jumpscares.

6. Charlie, Pim, and Bill vs the Alien

Poor Bill, we hardly knew ya. Introduced and later eviscerated in this episode, Bill is a flat-earther conspiracy theorist who thinks that he’s seen aliens. It turns out he’s right. The trio are abducted by aliens, and then those aliens are abducted by other aliens who bring the gang to an amazing space party. Bill has his guts eaten, but Charlie and Pim have an amazing time… until they find out the earth actually IS flat. Bill really was right all along.

5. Enchanted Forest

Unfolding with 1970s Lord of the Rings style animation, Enchanted Forest features Pim and Charlie accompanying a hobbit-like creature named Mip on a quest to make a princess smile. Pim is praised by the forest’s denizens for his epic deeds, while Charlie is totally ignored, twisting the critter into a Gollumesque villain consumed by envy.

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

If the number one slot on this list was reserved for the episode with the best title, Gwimbly: Definitive Remastered Enhanced Extended Edition DX 4K (Anniversary Director’s Cut) would surely win. Despite not being the greatest of all Smiling Friends adventures, it’s still comic gold. This bonkers episode centers around Pim and his new slacker partner Allen and their attempt to restore a down and out videogame character to its former glory. Gwimby hasn’t been able to star in any new video games due to a greedy company owning his I.P., so the pair decide to turn to crowdfunding, only to be set upon by the company’s CEO. Meanwhile, Charlie is tortured by a deranged creature named James, who forces the poor critter to dress up as a maid and bake him casseroles. It’s a stellar episode featuring the madcap plots and incongruous animation that makes the show so addictive.

3. Frowning Friends

There’s a new company in town… and its business model is spreading misery. Charlie and Pim meet their Frowning Friends doppelgängers Gnarly and Grimm, who have come to spread sorrow and woe and turn a profit in the process. Charlie and Pim have to remind the world that it is better to spread good will than ill. It’s the ultimate pessimist vs optimist showdown, and a surprisingly emotional reminder to always look on the bright side, even when it’s easier not to.

2. A Allan Adventure

A Allan Adventure is the first Smiling Friends episode dedicated to the company’s best worst employee. Mr. Boss gives Allan the simplest of assignments, something even the most uncaring slacker can handle: go to the store and get paperclips. Easier said than done. Allan ends up on an odyssey that includes but is not limited to helicopter chases and battles with undead pirates. It’s peak Smiling Friends ridiculousness from a fresh character perspective.

1. Desmond’s Big Day Out

Smiling Friends inaugural episode is still the greatest. Pim and Charlie and tasked with proving to the suicidal Desmond that life is indeed worth living, it just takes one fun day to prove it. Pim and Charlie bring Desmond out in town, and the depressed man keeps a loaded revolver pressed to his temple the whole time. Meanwhile back at the office, Allan is driven to the brink of insanity by an infestation bliblies. It’s hilarious, macabre, and even a little touching. Smiling Friends at its absolute best.

(Featured Image: Adult Swim )