Smiling Friends has really seemed like a rejuvenation of the much-criticized genre that is adult animation. In a sea of formulaic, cookie-cutter stories and character designs, Smiling Friends truly excels at standing out and bringing fresh and creative ideas to the table (in terms of both the animation and the writing).
Throughout Pim and Charlie’s many adventures, they encounter a vast audience of different characters, all of them unique in their own sort of way. Some have different designs, some have different quirks, and some have whole different art styles, which leads to a multitude of memorable characters on the screen at all times and several great Smiling Friends episodes.
The Boss
The man conceptually responsible for all of the duo’s adventures, The Boss is, as one may guess, their boss. Allegedly taking residence in the top half of the ‘Smiling Friends’ building, he is the man with the plan when it comes to finding work for Pim and Charlie.
Instead of being a completely new design, The Boss’s design hinges more on a caricature of a real person. With some dangerously stringy appendages and a larger-than-life head, The Boss’s slightly grotesque appearance and off-putting way of speaking make him play perfectly into Smiling Friends’ comedic tone.
Forest Demon
A prime example of how Smiling Friends excels at using different styles of animation to create one, cohesive, show, the Forest Demon appears in “A Silly Halloween Special” as a Claymation demon.
As well as being legitimately a bit scary, the demon’s unorthodox appearance truly makes it seem like an otherworldly creature, from some dimension where all characters are horrifying creations of clay. On top of his dimension skipping abnormalities, the demon’s appearance also really bolsters the payoff of the episode when the partygoers rip him apart and eat his insides for dinner. He certainly could have been one of Adult Swim’s most iconic villains if they stuck around for longer.
Simon S. Salty
While it may seem like a bit of a copout to include a literal person who has been green-screened into the cartoon as a “creative” character design, it still stands out as a unique choice and honestly works really well in terms of world-building.
While Smiling Friends may not get a lot of world-building, it’s inclusions like Simon S. Salty’s that really add a bit of depth to the world around Pim and Charlie. Aside from being a funny sight to see a real person existing in a cartoon world, it’s also just a cool concept that a real person would be able to live and coexist with the other wackiness that goes on in the world of Smiling Friends. Yes, even if he is brutally and repeatedly murdered.
Mip
Mip is a great example of a fun character done in a really cool way. Deep in the enchanted forest, the two heroes meet Mip, a traveling bard of sorts who joins the duo on their adventure to save the princess.
Taking a large amount of inspiration from the character of Bilbo Baggins in the 1977 Rankin/Bass animated film of ‘The Hobbit’, a clear link to the character can be seen in his hands, facial features, and especially in his eyes. In a field of wild creativity, it’s also really cool to see real-world inspiration shine through in some of the characters.
The Devil
It may seem difficult to put a creative spin on a figure who has appeared in so many instances of storytelling and media, but the Smiling Friends team does this by reworking his inner character while not necessarily overhauling his outer character.
He still looks like many artistic renderings of the devil, but the difference is in his personality – that of a teenage boy. Sitting in his room down in Hell, it seems like all the Devil does is hit his vape and play Rust while on Discord with his buddies. In fact, he wasn’t even able to go outside and get food himself, instead opting to get the Smiling Friends equivalent of ‘Uber Eats.’ And yes, they forgot the straw.
Jennifer
In attempt to win back their client, Shrimp’s, ex-girlfriend Shrimpina, Pim finds himself falling in love with the woman he thinks is Shrimpina. Fortunately for him, he doesn’t have to betray poor Shrimp, as who he thinks is Shrimpina is actually Jennifer.
In a world of complexity, sometimes simplicity is key. When the viewer is constantly bombarded with oddball characters and never-seen-before designs, it’s quite refreshing to see someone who is simply a human, no if-ands-or-buts. Although she may seem simple to the viewer, the funniest thing is that she’s probably the odd one out in the Smiling Friends’ world.
Wall Guy
Perhaps the most unreasonable character in all of Smiling Friends, the Wall Guy is, as his name would suggest, a guy who lives in the Smiling Friends’ wall. Fun fact, he’s also voiced by Finn Wolfhard.
Not only does he sport an all white, sort of obtuse design, but the unapologetic way in which he confronts Alan as if he’s in the wrong instantly subverts the scene, making a once bizarre character a straight man (and pulling off one of Smiling Friends’s many joke twists with flawless execution). The viewer still never finds out what’s on his computer, though.
Gym Guy
When Charlie and Shrimp head to the gym to look to start improving, the Gym Guy has some choice words about Shrimp’s squat form. When a show is as bizarre as Smiling Friends is, it may seem like they need to include a character that truly feels real to the audience. However, the Gym Guy does just that.
Gym Guy’s design provides a perfect juxtaposition between the know-it-all knowledge he’s pushing onto Charlie and Shrimp and his actual physique (which implies that he’s never done a squat in his life). It’s also an interesting choice to give him a completely normal voice despite the fact that he looks seventy, completely attributing his less than ideal appearance to his assumed health habits.
3D Squelton
When the Smiling Friends are put under some real competition by their rivals, the Frowning Friends, they begin to have to look anywhere and everywhere for someone they can make smile. And, after a bit of looking, who else would appear in a sandbox near them but 3D Squelton?
Probably the most bizarre looking character in Smiling Friends, the animators use the unconventional method of 3D stop motion to bring him to life. Aside from simply being fun to look at, 3D Squelton is the only character in Smiling Friends whose name is a homage to the way their character is shown on the screen.