The 10 Best Smiling Friends Episodes, Ranked

by

Animated television has thrived in the 2020s, particularly with more adult-oriented shows on Adult Swim. Leading the way has been Smiling Friends, a Cartoon Network series that recently concluded its three-season run. Created by Zach Hadel and Michael Cusack, the show centers around the Smiling Friends organization – Mr. Boss, Charlie, Pim, Allan, and Glep – and their endless efforts to bring happiness to others.

The show’s core idea became bigger than just Smiling Friends itself, as the audience grew with each new episode. Over its 27 episodes, the show delivers an incredible number of hilarious, wild, and memorable adventures. Episodes like “The Mole Man” and “Erm, the Boss Finds Love?” highlight the show’s remarkably creative and unpredictable nature.

10. “Mr. Frog”

(Season 1, Episode 2)

Mr. Frog has quickly become a fan favorite character on Smiling Friends, and it’s easy to see why. This former TV and presidential candidate brings a surprisingly insightful commentary on today’s world. The Smiling Friends attempting to help him represents a significant challenge for the duo, marking the first major test of their abilities throughout the series.

The challenges of trying to help Mr. Frog, who constantly causes trouble by eating and attacking people, really established the incredibly high comedic standard for Smiling Friends. The phrase “Hello, I’m Mr. Frog” has become so iconic that fans instantly think of it whenever they see this clumsy character.

9. “Charlie Dies and Doesn’t Come Back”

(Season 1, Episode 8)

This episode really showed how unpredictable and off-the-wall Smiling Friends could be. After Charlie unexpectedly dies, he finds himself in hell, needing to strike a deal with Satan. Surprisingly, the journey is easier – and just as funny – as you might imagine. Charlie often walks a fine line between being endearing and a downer, especially when contrasted with Pim’s cheerful personality.

Charlie’s descent into hell is filled with unforgettable scenes. Highlights include a surprisingly relatable encounter with Satan – portrayed as a tired, gaming enthusiast – and a humorous funeral eulogy delivered by Mr. Boss, which quickly became popular online.

8. “Charlie, Pim, and Bill vs. The Alien”

(Season 2, Episode 5)

In this episode, Pim tries to connect with his best friend and coworker, Charlie, by introducing him to his group of friends—who are obsessed with UFOs. Charlie is a skeptic, but his views change drastically when he and Pim are unexpectedly abducted by aliens. The episode then becomes a fast-paced and exciting tribute to classic science fiction horror, as the two friends struggle to avoid an unwanted examination.

The humor in Smiling Friends really shines when paired with this over-the-top storyline. Just like the strongest episodes, the surprise twist is made even better by its funny reveal. There’s a hidden layer to who’s taken Pim and Charlie, and their reaction to the truth is hilarious—especially when they learn the Earth is flat!

7. “The Curse of the Green Halloween Witch”

(Season 3, Episode 4)

The latest episode of Smiling Friends, “The Curse of the Green Halloween Witch,” is easily its most wild and over-the-top yet. It’s a clear tribute to the horror genre, building on creepy themes and references the show has used before, but taking things to a whole new level. When the Smile Friends refuse to give money to a Green Witch, she curses them, leading to unsettling body horror, nods to classic franchises like Silent Hill, and a visually chaotic experience.

Even for those who love horror, this episode is genuinely frightening. Hadel and Cusack really went above and beyond, creating something intensely unsettling yet still distinctly Smiling Friends. It’s a very serious ten minutes, but it never loses the core appeal of the show. The ending offers a surprisingly lighthearted, *Wizard of Ozesque explanation that provides relief and even some laughter. Despite this, the episode leaves a lasting impact, uniquely disturbing its audience.

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

(Season 2, Episode 1)

This episode lives up to its lengthy title – it’s delightfully bizarre. The season 2 premiere is both a loving tribute and a funny look back at the video game industry, from its golden age to its current challenges. The story revolves around Gwimbly, a forgotten platforming hero reminiscent of Mario and Rayman. He’s an outdated, awkward, and often inappropriate character, making him an ideal ‘patient’ for the helpful, yet eccentric, Smiling Friends.

Gwimbly stood out because his art style was different from the other main characters. Smiling Friends really shines when it mixes animation styles in inventive ways. Gwimbly’s unusual 3D, pixelated look is central to this wild episode, and moments like Allen spraying him with “Dirty Brown Water” are particularly memorable.

5. “An Allan Adventure”

(Season 2, Episode 3)

Allan from Smiling Friends is a fan favorite, and often the highlight of the show. Bill Cunningham’s voice work as Allan is consistently hilarious. Many viewers find Allan incredibly relatable – he’s been compared to Squidward from SpongeBob SquarePants. That’s why his standalone episode, where he searches for paper clips, is so memorable – it’s a surprisingly grand adventure.

“An Allan Adventure” is a funny episode where Allan faces a series of mishaps, from a comical encounter with a spider to being stranded on a deserted island. It highlights how often Allan feels like an outsider with his friends and colleagues. The surprising ending, and Mr. Boss’s ‘gift’ to Allan – a mini-figure of himself – are particularly amusing, especially Allan’s blunt response: “Um… I don’t really want this.”

4. “Silly Samuel”

(Season 3, Episode 1)

While the season opener kicked off the show’s last season, it wasn’t the main plot that made this episode stand out. Instead, the hilarious subplot with Mr. Boss and Allan trying to avoid the building inspector is what immediately put it among the best Smiling Friends episodes. Mr. Boss is always a fan favorite and a bit of an enigma, and this episode finally revealed some of his backstory – including the fact that he didn’t exactly follow the rules when building the Smiling Friends headquarters.

Some of the most memorable moments from Mr. Boss include his lines, “Allan, we are so screwed” and the repeated question, “Do you realize, do you realize?” These quickly became popular internet memes. The ending is also hilarious – the building inspector becomes friends with the group only to then vanish into dust. The line, “Yo guys, it’s me Charlie… Hey, did that guy just turn into sand?” is sure to remain a classic quote.

3. “Pim and Charlie Save Mother Nature”

(Season 3, Episode 5)

This episode, like the earlier “Silly Samuel,” focuses on Mr. Boss and Allan. Allan, the stressed-out office manager, is still working even on a company retreat at Mr. Boss’s cabin. The Smiling Friends are finally getting a vacation after a previous attempt didn’t work out, but they can’t seem to reach Allan. While Pim and Charlie embark on their own funny adventure, Mr. Boss tries to cheer Allan up with cookies and get him to relax.

The episode takes a truly bizarre turn when Allan develops an intense obsession with cookies, even to the point of eating them off of Boss’s chest. It’s one of the most unexpectedly funny and strangely intimate moments in Smiling Friends, and the sheer randomness makes it even funnier. Despite this, Allan never displays any romantic feelings for Boss before or after this scene. However, the episode unexpectedly portrays them as a surprisingly endearing couple.

2. “Enchanted Forest”

(Season 1, Episode 6)

“The Enchanted Forest” shares similarities with the “Pim and Charlie Save Mother Nature” episode in its playful approach. It begins as a funny take on fantasy adventures, poking fun at movies like Lord of the Rings and video games such as Super Mario and Skyrim, and is filled with amusing side missions. Pim and Charlie embark on a quest to cheer up a princess who’s being bothered by a stalker, and they quickly find help from a local named Mip.

This episode stands out because of the unexpectedly hilarious banter between Charlie and Mip. The contrast between their playful interaction and Pim’s growing frustration with the adventure’s lack of progress makes it even funnier. And the surprise reveal about Mip adds another layer of humor to the whole thing.

1. “The Smiling Friends Go to Brazil”

(Season 1, Episode 9)

The Season 1 finale, “Smiling Friends Go to Brazil,” might be overlooked, but it’s a brilliant example of subtle, passive-aggressive comedy. The episode follows Pim, Charlie, Allan, and Glep on a trip to Brazil that immediately hits a snag – nobody booked a hotel! They’re left stranded at the airport, and even Mr. Boss can’t fix it. The next ten minutes are filled with awkward politeness as the group tries to maintain a friendly facade while clearly being frustrated and annoyed.

If you have a lot of friends, you’ll understand this situation: when someone you care about does something silly, but you don’t want to get mad at them. In this episode of Smiling Friends, the characters never raise their voices – instead, they deal with awkward silences, chaotic travel, and go out of their way to be polite, all while showing their unique chemistry. This understated humor isn’t for everyone, but it makes this episode the strongest of the series so far.

Read More

2026-05-04 01:09