The BEST episodes of Smiling Friends
Every episode of Smiling Friends ever, ranked from best to worst by thousands of votes from fans of the show. The best episodes of Smiling Friends!
Smiling Friends Inc. is a small company whose main purpose is to bring happiness to its clients. The series follows the day-to-day lives and misadventures of its representatives, the lazy, cynical Charlie, and the cheerful, optimistic Pim, as they try to cheer up and comfort the troubled people who call their company's hotline and help them out with their problems.
#1 - Curse of the Green Halloween Witch
Season 3 - Episode 4 - Aired 11/2/2025
The Smiling Friends get cursed by a witch *gulp*... scawyyy!
#2 - Charlie, Pim, and Bill vs the Alien
Season 2 - Episode 6 - Aired 6/10/2024
This episode tells the story of a thirty-four year-old boy named Pim who sets out to save his mother on Mars after she is abducted by Martians.
#4 - A Allan Adventure
Season 2 - Episode 3 - Aired 5/20/2024
Allan is tasked with finding more paper clips for the office. *Spits on you*
#5 - Squim Returns
Season 3 - Episode 6 - Aired 11/16/2025
After buying a magic mirror, Pim meets Squim. Meanwhile, Charlie starts "digging deep" and gets into some reallllly bad Internet stuff...like REALLY bad stuff. Not in a good or funny way. At ALL.
#6 - Charlie Dies and Doesn't Come Back
Season 1 - Episode 8 - Aired 1/10/2022
In the season finale, Charlie actually dies for real.
#10 - Shmaloogles
Season 3 - Episode 7 - Aired 11/23/2025
Pim, Charlie, and Flint discover a new realm full of wacky characters that you're absolutely gonna love. Although, something happens, and Pim now has his own adventure...huh?
#11 - The Magical Red Jewel (aka Tyler Gets Fired)
Season 2 - Episode 7 - Aired 6/17/2024
The Boss and Pim fight for their lives in a mysterious world called Spamtopia. Meanwhile, Charlie confronts Allan over something serious.
#12 - Gwimbly: Definitive Remastered Enhanced Extended Edition DX 4k (Anniversary Director's Cut)
Season 2 - Episode 1 - Aired 4/1/2024
The classic gang help a disgusting, vile, loser they found on the streets. However, Allan sprays him with the hose.
#13 - Frowning Friends
Season 1 - Episode 7 - Aired 1/10/2022
A rival business moves across the street, much to the Boss's dismay. Nuff said.
#14 - Enchanted Forest
Season 1 - Episode 6 - Aired 1/10/2022
Pim and Charlie are beckoned into the mysterious Enchanted Forest by a princess and encounter all sorts of insane toon characters along their journey.
#15 - Friend-Bot (Version 12589218731809213528796879521)
Season 3 - Episode 9 - Aired 4/12/2026
[LOGLINE REDACTED FOR VIOLATING TERMS AND SERVICES]
#16 - Desmond's Big Day Out
Season 1 - Episode 1 - Aired 4/1/2020
A small company dedicated to bringing happiness to the world receives a simple request to help a woman’s unhappy son smile again, but the job turns out to be more complicated than it seems.
#18 - Silly Samuel
Season 3 - Episode 1 - Aired 10/5/2025
Pim and Charlie are tasked with helping a stupid ugly freak no one likes. Meanwhile, the Boss and Allan... read more.
#19 - Pim Finally Turns Green
Season 2 - Episode 8 - Aired 6/24/2024
After eating a mysterious artifact found at an ancient burial ground, Pim suddenly and mysteriously turns bright green, concerning his friends and rivals. At first, everyone is horrified, but eventually they learn to accept and love "The New Green Pim".
#20 - Brother's Egg
Season 2 - Episode 5 - Aired 6/3/2024
After some of the Boss's usual tomfoolery, Pim and Charlie are tasked with helping a mad scientist with an "egg dilemma".
#21 - A Silly Halloween Special
Season 1 - Episode 4 - Aired 1/10/2022
Pim ventures into the forest across the road to fetch firewood for the office Halloween party.
#22 - Erm, the Boss Finds Love?
Season 2 - Episode 4 - Aired 5/27/2024
DISCLAIMER: Just a heads up, this is the scariest episode of any cartoon that's ever been created, so… yeah. We're not legally allowed to tell you what happens in this episode, you just need to watch it (if you do decide to do that, which you shouldn't).
#23 - Shrimp's Odyssey
Season 1 - Episode 3 - Aired 1/10/2022
When a pathetic shrimp calls the Smiling Friends hotline after being dumped, Shrimpina, Pim and Charlie have very different ideas about how to handle the situation. The audience finally votes on the cool new fifth Smiling Friend, Smormu.
#24 - Who Violently Murdered Simon S. Salty?
Season 1 - Episode 5 - Aired 1/10/2022
Who is famous food tycoon Simon S. Salty? Why was he brutally murdered in his own restaurant? Who done did do that there murder? Huh?
#25 - Mr. Frog
Season 1 - Episode 2 - Aired 1/10/2022
After beloved frog celebrity Mr. Frog gets into hot frog water, Pim and Charlie are tasked with helping the frog get things back on frog track. Meanwhile, Glep has a crazy side adventure that has the critics going wild.