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Season 1

    Pim's Family 

Pim's Family

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"I have no love for you in any shape or form. Right, babe?"
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"STEVEN! GET IN HERE AND SIT AT THE DINNER TABLE!"
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"OH WOULD YOU SHUT THE [bleep] UP, WOMAN?! I WAS DOWN IN THE BLOODY MINES FOR FOURTEEN HOURS TODAY!"
Voiced by: Michael Cusack (Pim's Sister, Mother and Father), Nick Wolfhard (Graham Nelly), Tom Fulp (Amy's Boyfriend)
Pim's Dysfunctional Family whom he hasn't visited since Christmas.
  • Abusive Parents: The neglectful type. The youngest kids are wild cards roaming across the background of the scene while the elder siblings are having dinner. They still provide some parental guidance, at least back when Pim was still a child.
  • Alcoholic Parent: Both parents, the mother moreso. She holds a glass of wine in her hand while keeping the bottle(.png) to her right.
    • Might be even. As a flashback in "Enchanted Forest" shows that Pim's father, Steven, would hold a beer bottle while walking down the sidewalk with his son.
  • Ambiguously Trained: According to one of the picture frames that Zach elaborates on in an interview, Pim has a brother that served in Afghanistan. It's unknown if he returned.
  • Awful Wedded Life: It would seem that its nothing but Dead Sparks between the parents.
  • Big Brother Bully: A gender-flipped example; Pim's sister Amy flat-out tells him that she lacks any positive feelings toward her younger brother.
  • Big SHUTUP: "AW, WOULD YOU SHUT THE ~BLEEP~ UP, WOMAN?! I WAS DOWN IN THE BLOODY MINES FOR FOURTEEN HOURS TODAY!"
  • The Bogan: Angry Australian blue collar slobs, the lot of them.
  • Character Tic: Amy provides her boyfriend with several pecks on the bicep whenever she asks him something.
  • Cool Board: Averted. The only skateboard Graham Nelly owns is a Tech Deck.
  • Creator Thumbprint: Most of co-creator Michael Cusack's other works satirize Australian culture and society, and Pim's family allows him to do this in Smiling Friends despite the show being set in Eagleland.
  • The Ditz: Graham Nelly doesn't seem to be quite there.
  • Face of a Thug: Amy's boyfriend looks like a stereotypical Jerk Jock, but is implied to be a polite and nice person, given that he insists that he ruined the dinner and apologizes profusely when he vomits.
  • Fantasy-Forbidding Father: Justified. When Pim was a child and expressed a desire to embark on a magical quest in the Enchanted Forest, his father forbade him. Steven didn't do this for petty grievances, as he clearly reasoned to his son that he was just a child who didn't have the unrelenting dedication, bravery, and wisdom needed of a more mature hero to survive the Forest, and still went to reassure him that he might become that one day.
  • Five-Second Foreshadowing: Graham's supposed skateboarding ability is immediately cast into doubt when you see his pot belly and man-boobs.
  • Free-Range Children: There's one writing on the wall, another climbing through the insulation in the walls, and at least two more running around the house.
  • Gentle Giant: Amy's boyfriend is a gigantic, muscular man who is also incredibly polite and patient, given how he doesn't mind the constant racket going on from his in-law's arguing and when he vomits, he apologizes profusely and insists that he ruined the entire family dinner.
  • Gonk: The rest of Pim's family at least somewhat resembles him, but Cousin Graham has a weirdly realistic face and head.
  • Hair Today, Gone Tomorrow: Steven had a brunette upward fringe, a clean-cut face, and hairy arms when Pim was a little boy, but in the present he only has a combover and a shaved stubble on his arms and chin.
  • Huge Guy, Tiny Girl: Amy is about a third of the size of her muscular boyfriend.
  • Implausible Boarding Skills: Averted. Despite Pim's high praises for his cousin, Graham can barely keep a hold on his Tech Deck.
  • Jerkass: Pim's family are all shown to be downright abhorrent self-centered jerks, with the exception of Graham, who seems to be on good terms with Pim, and Amy's Boyfriend, who apologizes politely after barfing.
  • Lady Drunk: The mother is of the wine-addicted white trash variety.
  • Lovable Jock: Amy's boyfriend, he's a ripped dude who definitely spends a lot of time at the gym, and he's shown to be a soft-spoken and patient person who has good manners, as he doesn't make any complaints about how noisy and dysfunctional his in-law's home is, and apologizes profusely and insists he ruined the dinner when he abruptly vomits.
  • Nice Guy: Averted hard for most of the family itself, but Implied with Amy's boyfriend, who seems genuinely apologetic for vomiting at the dinner table. Graham is a lesser example, in that, while he's a bit off, he certainly is far more polite and accommodating to Pim and his friends compared to his blood relatives, even showing off his mini-skateboard trick.
  • No Indoor Voice: The parents scream at each other due to Steven refusing to be in the same room as the rest of his family.
  • No-Neck Chump: Amy's boyfriend.
  • No Name Given: Pim's mother, Amy's boyfriend, and the kids running around in the background are never mentioned by name.
  • Parents as People: Steven forbids Pim from entering the Enchanted Forest, but he also makes it clear that he simply lacked the bravery, wisdom and strength to enter, and also that he could one day be worthy. Completely averted by his appearance in the present, in which he takes his time off his 14 hours of work a day to watch TV, not giving any attention to his kids or even noticing Pim's appearance.
  • Pet the Dog: A mild example with Pim's mother. While she's clearly a drunk, she does scold Pim's father for not sitting at the dinner table with the rest of the family when their son is home, implying that she does love him somewhat, at least compared to his far worse sister and father.
    • A flashback in Enchanted Forest also shows that Steven also does love him somewhat, sharing a Tom Brady-style kiss with him.
    • Amy showed slight concern of her boyfriend when he vommited on the dinner table.
  • Phoneaholic Teenager: Amy holding her phone over her dinner.
  • Psycho Pink: Downplayed. They have pink skin just like Pim does, and are all highly unpleasant individuals, with the exception of Graham, who's a lot more polite and on good terms with Pim. Amy's boyfriend is a straight up aversion, due to having a natural skintone as well as being implied to be a very pleasant person, if his tolerance of the constant racket in Pim's family home and good manners when apologizing are any indication.
  • Shared Family Quirks: Pim, his dad, and his sister have all demonstrated a willingness to give random, pecking kisses to people with no warning. It's implied that his dad regularly kissed his children on the mouth.
  • The Short Guy with Glasses: The kid drawing a Cool S on the wall.
  • Shout-Out: Steven (Pim's father) dresses like a cross between Hank Hill and Peter Griffin in Pim's flashback in "Enchanted Forest", having a hairstyle and glasses that invoke the former while wearing a shirt and pants that are similar to the latters. In the present day he resembles Homer Simpson.
  • Smart People Wear Glasses: Steven wore glasses in a time back when Pim was bespectacled kid and he gave his son reasonable advice on fantasy quests.
  • Smarter Than You Look: Amy seems to be surprisingly well-spoken and eloquent in spite of her Valley Girl appearance and voice, as she tells her brother Pim "I have no love for you in any shape or form." when insulting him.
  • Smoking Is Not Cool: Pim's dad, Steven, is sitting with a cigarette in his right hand.
  • Stress Vomit: Implied, despite how big and chill Amy's boyfriend appears he suddenly vomits, likely from the chaos in his girlfriend's household.
  • The Stoic: Amy's boyfriend doesn't say anything until he vomits over his plate and profusely apologizes, insisting that he ruined the family dinner.
  • Took a Level in Jerkass: Pim's dad, Steven. In a flashback it's shown that he was a more decent person aside from his bizarre Tom Brady-style habit of kissing his kids on the mouth, as his response to Pim telling him he wants to go on an adventure in the enchanted forest is to encourage him that he needs to be a hero with unrelenting dedication, bravery, and wisdom, which is jarring compared to the present version of himself, where he's an overstressed, constantly angry schlub who hates his wife as much as she hates him.
  • Too Many Babies: Pim's parents appear to have had somewhere between four to six children.
  • Valley Girl: Amy is a generic example of the Stock Parody.
  • Vocal Dissonance: Amy's boyfriend has a soft and gentle voice, unfitting of his huge muscular build and impressive height.
  • Younger Than They Look: Pim's mother has at least three young children, so she can't be much older than her early fifties. In spite of this she's got excessive wrinkles on her face, neck and arms, likely a result of the stress of raising too many kids in a loveless marriage.

    The Squatter 

The Squatter

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"By the way, for the record, you should probably knock or make yourself known before you enter someone's place."
Voiced by: Finn Wolfhard
A squatter with a computer set up in the walls of the break room.
  • Basement-Dweller: Not even in the basement, he just loiters in the oddly spacious walls.
  • Embarrassing Browser History: Frantically tries to close his browser window and then physically moves to cover his computer screen with his hands once Alan tries to get his attention.
  • Jerkass: He's pretty damn rude when it comes to his privacy, which is made worse given he's a huge hypocrite.
  • Straw Hypocrite: Preaches privacy étiquette to the office worker that finds him hiding on their property.

    TV Alien 

TV Alien

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"Blek. Bog bek. Abya, ga giliclub."
Voiced by: Zach Hadel
Modeled by: Chris O'Neill
A 3D model of a dancing alien humanoid, and the entire focus of a television program watched by Pim and his father.

  • Accent Upon The Wrong Syllable: His Motor Mouth turns "Hello, thank you for watching!" into "HEL-LO thankyouforwatching!"
  • Black Bead Eyes: It appears to be entirely pupils, but as Chris O'Neill shows in this tweet, that's not the case.
  • Breaking the Fourth Wall: Physically breaks through its fourth wall to verbally break the show's by thanking the viewer.
  • Dark Is Not Evil: Looks creepy, but is clearly a well-liked entertainer and even thanks the viewing public at the end of his episode (though Charlie and Alan are still very creeped out by his appearance).
  • Incredibly Lame Fun: It's just a dancing alien, which somehow has it's own show. Pim even remarks that the spin it did when Charlie wasn't looking as being "cool" which was the entire reason why he was showing it to Charlie.
  • Leitmotif: Dances to electronic music.
  • Motor Mouth: When he speaks at the end of the pilot, he repeatedly states five words in the space of two seconds.
  • Running Gag: Shows up three times throughout the cartoon, paying off with its third appearance.
  • Suddenly Speaking: Is largely The Unintelligible until just before the credits. "hello thank you for watching :-)"
  • Television Portal: It erupts from the break room's TV, sending a shower of broken glass across the floor and horrifying everyone.
  • Visual Pun: It breaks out of the wall of the TV to thank the viewer, therefore breaking the fourth wall.

    Party Bro 

Party Bro

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"Dude, what the [bleep]? Why are you [bleep]ing here man?"
Voiced by: David Dore
A rotoscoped guy who enjoys parties.
  • Art Shift: He is animated using rotoscoping.
  • Berserk Button: Whatever you do, don't wear blackface around him, or he'll kill you.
  • Everyone Has Standards: He's a huge dick to Pim for no reason, but he takes issue with someone crashing his Halloween party while wearing blackface (or so he thinks).
  • Hypocrite: He makes fun of Pim for looking old and ugly, while he himself looks like a humanized version of Watto.
  • Life of the Party: He's called Party Bro for a reason.
  • Jerkass: Zig-Zagged. He bullies Pim in the pilot, but afterwards he appears to have become an acquaintance to the Smiling Friends, implying that he is on better terms with him.
  • Younger Than They Look: He looks like an old man, but is apparently college-aged.

    Dave 

Dave

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Dave himself.
The creator of Daveland.
  • The Cameo: Shows up in the Season 1 Finale at Charlie's funeral.
  • The Generic Guy: An ordinary looking white dude with a completely blank expression on his face, who nonetheless has an entire theme park devoted to himself.
  • Inexplicably Awesome: For some reason he made a theme park all about himself despite seemingly being an average human.
  • Ridiculously Average Guy: He's so completely unremarkable, that paradoxically the only thing remarkable about him is how unremarkable he is. Nevertheless, he somehow has his own theme park named and themed after himself.
  • Rule of Funny: The entire reason for his existence, given that he's a completely unremarkable human who has an entire theme park themed after and devoted to himself.
  • Nice Guy: Implied. Given that he takes his time out of running his theme park to show up to Charlie's funeral in person in spite of having no apparent reason to do so outside of being company.
  • Special Person, Normal Name: Parodied. Pim outright admits that he doesn't know who Dave is when Desmond questions him on the identity of the latter, despite being a regular at Daveland.
  • The Voiceless: He is not seen speaking.

    Bug 

Bug

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"You know, I knew Mr. Frog had problems. I just never knew they went that deep."
Voiced by: Mick Lauer
Mr. Frog's co-star on The Mr. Frog Show.
  • A Dog Named "Dog": He's a bug, and his name is Bug.
  • Corpsing: In-Universe, he noticeably cracks a smile when Glep does his spit routine during rehearsal.
  • The Danza: invoked He is credited on the Mr. Frog Show by his real name.
  • Eaten Alive: Happens to him in every episode of The Mr. Frog Show.
  • Getting Eaten Is Harmless: It's safe to assume that him being eaten by Mr. Frog does him no harm, as he is still around and has been in every episode of The Mr. Frog Show.
  • Small Name, Big Ego: He tells Glep that he was the one who carried The Mr. Frog Show in spite of Mr. Frog's demons.
  • Vocal Dissonance: He has a deep, but natural sounding voice in spite of being a tiny, cartoony looking insect.

    Shrimpina/Jennifer 

Shrimpina/Jennifer

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"What can I get for ya?"
Voiced by: Erica Lindbeck
Portrayed by: Laina Martinez (live action)
Shrimpy's ex, a strangely human character in a world of beautiful little characters. Her actual name is Jennifer, and Pim inexplicably mistakes her for Shrimpina.
  • A Dog Named "Cat": A beautiful human woman named "Shrimpina". Except no, her name is Jennifer, and as Charlie points out, the fact that she isn't a shrimp should have been Pim's first clue that he was talking to the wrong girl.
  • Mistaken Identity: She isn't Shrimpina, her name is Jennifer, and she has never met Shrimp in her life. Pim went to the wrong place.
  • The Mourning After: She mentions trying to move on from her last boyfriend when Pim meets her. Pim thinks she's talking about breaking up with Shrimp, but she was actually talking about recovering from her previous boyfriend Jason dying in a motorcycle accident several months before.
  • Nice Girl: She really is a sweetheart, enough so that Pim falls for her immediately (and dreams of starting a relationship and building a romantic life with her complete with kids), and even when Pim introduces her to Shrimp and it looks like she's getting annoyed by the misunderstanding and insulting Shrimp over his unattractiveness and gamer lifestyle, she actually reveals he's her ideal man and they immediately start making-out.
  • Non-Indicative Name: Her name is "Shrimpina" but she's a human woman. It's actually a subversion, as it later turns out that her name is actually Jennifer and Pim had gone to the wrong place looking for the real Shrimpina. This is lampshaded when Charlie asks Pim how he could have possibly thought she was Shrimpina, and Pim replies that he just assumed it was a standard Bait-and-Switch gag..
    Charlie: Pim, her name is Shrimpina...she'd be a shrimp.
    Pim: I did think that for a moment, I just thought it was gonna be a quirky "you didn't expect she was gonna be a human" thing.
  • Non-Standard Character Design: Even compared to other human characters that aren't live-action actors, she has more realistic features that resemble stock vector art.
  • Ooh, Me Accent's Slipping: Loses her southern accent halfway through the episode without explanation.
  • "Shaggy Dog" Story: Wasn't actually Shrimpy's ex, she was completely unrelated to Shrimpy's story. Pim really needs to get his eyes checked. Subverted in that they do get together.
  • Southern Belle: She's pretty and has a southern accent (sometimes).
  • Strangely Arousing: Apparently, a 4'6" shrimp with a receding hairline and likes playing Mouse Quest is literally everything she has ever dreamed about.
  • Trademark Favorite Food: Loves spaghetti, specially from Spaghetti Disco.
  • Ugly Guy, Hot Wife: Was this to Shrimp, as she turns out to be a very attractive human woman, despite the former not only being a talking shrimp, but an overweight, partially-bald, geeky one at that. Double Subverted, as she turns out to actually be a complete stranger that Pim had mistaken for Shrimpina, but still hooks up with Shrimp in the end as she still finds him attractive.
  • Walking Spoiler: In case it wasn't obvious.

    Simon S. Salty 

Simon S. Salty

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"I'm Simon S. Salty and I built this very restaurant with my own two hands!"
Played by: Perry Caravello
The CEO of Salty's. Was just killed.
  • Asshole Victim: He's not a nice or empathetic guy, given that he doesn't care at all about the 15 people his restaurants menu has killed, and makes fun of the FDA for declaring his food a public health hazard. The victim part is subverted when it turns out that none of the mascots killed him and he wound up dying of a heart attack from eating what is presumably one of his own restaurants burgers.
  • Alliterative Name: Simon S. Salty.
  • Bad Boss: One could think how good of a person was he to his workers to instigate murder. Played With. While he himself dies of a heart attack, every single one of the mascots still attempted to kill him while he's dead, for reasons such as....being not allowed to kiss while at work...? There's also him chaining Century Egg up in a hidden room in his restaurant just because the menu item corresponding to him didn't sell very well.
  • Corrupt Corporate Executive: Downplayed. He doesn't give a damn that his food has killed 15 people and makes fun of the FDA for declaring it a public health hazard, but is clearly afraid enough of legal action to change it to a healthier menu.
  • Greasy Spoon: His restaurant puts extra emphasis on greasy.
  • Heel–Face Door-Slam: Was planning to start eating healthy, but ends up dying of a heart attack when eating what was supposed to be his last burger.
  • Hollywood Heart Attack: He died from a fatal heart attack after taking one bite of a burger before eating healthy.
  • Karma Houdini: Subverted. At first it seems that with his death and his mascots running amok in the world of Smiling Friends, it seems that he's gotten his posthumous retribution for his restaurant's menu items killing over 15 people over the course of 4 months, but "Charlie Dies and Doesn't Come Back" reveals that not only is his restaurant somehow back in business, but it also returned to its iconic dangerously-unhealthy-yet-delicious menu.
  • Karmic Death: It's revealed that he died from a heart attack after eating what is presumably one of his own burgers, after mocking the FDA for taking action against his restaurant due to his burgers causing fifteen deaths over the course of four months.
  • Lack of Empathy: Played With. He doesn't care at all for the fact that his restaurants menu has killed 15 people over the course of 4 months, and even makes fun of the FDA for declaring his food a public health hazard, but changes the menu to unappetizing, but healthy food anyways, likely because of threats of legal action.
  • Mysterious Middle Initial: What the "S" stands for is never mentioned.
  • Non-Standard Character Design: He stands out among even among the other characters that this trope applies to by the virtue of being played by a live-action actor superimposed into a 2D Cartoon world.
  • Nutritional Nightmare: The food he normally serves has been deemed hazardous by the FDA, and linked to fifteen deaths over the course of four months. This forced him to completely revamp the menu with items that are healthier, but completely unappetizing, which pisses Charlie off.
  • Older Than They Look: Was apparently 77 when he died according to the In Memoriam gag, 18 years older than his actor.
  • Plot-Triggering Death: Charlie, Pim, and Ketchup find him dead on the couch in his office, and the Boss of the Smiling Friends orders them to solve his death.
  • Stylistic Suck: The body language of his actor, Perry Caravello, is deliberately as unnatural and unconvincing as possible for comedic effect. An example of this is him sticking out his arm when Ketchup shoves him to brace his fall and moving at a slow enough speed to not accidentally injure himself in an incredibly obvious fashion.

    Inhabitants of the Enchanted Forest 
Voiced by: Michael Cusack (Witch, Goblin, fairies), Joshua Tomar (Centaur), Mick Lauer (Elf), David Dore (King Alien)
The many wonderful beautiful little characters native to the enchanted forest. Includes goblins, centaurs, witches, and even aliens.

    DJ Spit 

DJ Spit

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"I always wanted to be a SoundCloud artist, man."
Voiced By: Zach Hadel

An aspiring SoundCloud rapper living in the streets. Like many others, his dreams were squandered by the Frowning Friends.


    Mr. Man 

Mr. Man

Voiced by: Lyle Rath
Another unfortunate critter who's been visited by the Frowning Friends.
  • Deadpan Snarker: Delivered in Lyle's iconic monotone, save for his brief breakdown.
  • The Grotesque: Implied, as the shape of his head was what the Frowning Friends focused on to keep him frowning.
  • Hulking Out: A REALLY bizarre example. When he freaks out and starts panicking when he thinks the Smiling Friends are messing with him, his head morphs into that of DJ Spit's.
  • Madness Mantra: Much like DJ Spit, demands the Smiling Friends to get out of his head as he thinks they're deceiving him. Taken to the extreme with his head and voice morphing into DJ Spit's as it gets worse.
  • Mind Screw: When he gets angry at Pim and Charlie, his head suddenly morphs into that of DJ Spit of all people, he repeats DJ Spit's Madness Mantra, and he even pulls out a gun and threatens them in a similar manner. Why exactly is anyone's guess, as both characters' have wildly different personalities and interests (Mr. Man wants to eliminate Puerto Ricans while DJ Spit is himself Hispanic) and it is confirmed that they can't be the same person, as we see both of them in the crowd of the Frowning Friends' event, which means a Jekyll & Hyde dynamic isn't really possible. Rule of Funny is most certainly in play here.
  • Politically Incorrect Villain: Outright admits that he wanted to kill the Puerto Ricans as well after the Frowning Friends are revealed to be hypocrites.

     3 D Squelton 

3D Squelton

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"Boo hoo!"
Voiced by: Harry Partridge
A large-headed... man whose dreams of becoming a balloon maker were dashed by the Frowning Friends.
  • Berserk Button: Lying, if him angrily yelling "3D Squelton hates lies! Boo-hoo!" when Grim breaks down crying out of fear for his life when the Boss aims an assault rifle at him, exposing him as a hypocrite directly after he makes a large speech about nihilism and misery in front of a huge crowd that he was in is any indication.
  • Character Catchphrase: "Boo-hoo!"
  • Dub Name Change: He's named Bébé 3D in the French dub.
  • The Eeyore: Sits and shouts "boo hoo" whenever things go pear-shaped.
  • Gonk: Hoo boy... The design team really pounced on the chance to use a 3D model to make him look awful.
  • Meaningful Name: 3D Squelton is indeed 3D.
  • Non-Standard Character Design: Rendered in 3D with very few frames of animation.
  • Third-Person Person: You're gonna remember his name. It's 3D Squelton.
  • Vague Age: Pim calls him "little guy" and he's first seen moping in a sandbox at a playground, plus his habit of referring to himself in third person is quite childish, as well as his interest in balloons, yet at the same time, his rant about the state of the world is quite eloquent and well-spoken, not to mention that no ordinary child would have such a pessimistic view of the world as he does, plus, he has an elderly looking appearance due to his wrinkly face.

    The Renaissance Men 
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FIRE!
A mysterious group of men who Charlie offhandedly mentions are coming to town.
  • Art Shift: One of them appears to be rotoscoped.
  • Asshole Victim: Narrowly averted. They kill Grim and Gnarly seconds after they make their Heel–Face Turn.
  • Ax-Crazy: Considering that they open fire on Grim and Gnarly with a hail of arrows, killing them instantly, without any motive or reason to do so, it's safe to say that they are a bunch of violent thugs.
  • Brick Joke: Charlie mentions at the start of the episode that the Renaissance Men are coming to town and says that "it's probably important". Lo and behold, at the end of the episode they do come to town and murder Grim and Gnarly.
  • Diabolus ex Nihilo: Ironically, they are this to yet another Diabolus ex Nihilo.
  • Non-Indicative Name: Lampshaded by Pim. Despite being known as "the Renaissance Men", he points out that they look more like they're from the High Middle Ages than from the Renaissance.
    Pim: That's like a completely different era!
  • The Spook: Played for Laughs. They are Medieval knights known as the "Renaissance Men" who randomly come to town and kill Grim and Gnarly without any seeable motive or cause. Charlie claims that "The Renaissance Men are coming to town" is the extent of his knowledge when Pim points out the absurdity of the whole thing.

    The Boss' Financial Advisors 
Voiced by: Lyle Rath (Warren Buffett), Zach Hadel (Mr. Peanut, Ronald Reagan)
The Boss's hallucinatory advisors, consisting of Warren Buffet, Mr. Peanut, and Ronald Reagan.
  • The Cast Show Off: The reason for one of them being Ronald Reagan is likely so Zach can show off his Reagan impression.
  • Corrupt Corporate Executive: Mr. Peanut got in hot water with the American public for filling his peanuts with toxic pesticides and decided the best way to apologize was by going on the Dick Cavett show to do a "peanut jig."
  • Hallucinations: Revealed to be so when Alan calls out his name.
  • Helpful Hallucination: Subverted, as they represent Boss struggling to find a non-violent way to compete with the Frowning Friends. Their advice consists of feeble marketing stunts, vague restructuring suggestions, and a flailing push to have the Boss buy more stocks of his failing business.
  • Only Sane Man: Downplayed. Ronald Reagan is the only one whose advice comes even close to being helpful, and even then, it's too vague to be of any actual help, as he quite literally suggests that he "try a more competetive business model" without explaining how to properly do so.
  • Shout-Out: Although the basic concept of Mr. Peanut is based on the Planter's Peanuts mascot of the same name, his skin tone, nose, voice, posture, and utter disregard for customers' well-being all clearly resemble Mr. Burns from The Simpsons.
  • Token Evil Teammate: Mr. Peanut is the most blatantly corrupt of the three, having filled his products with toxic pesticides, and presumably getting away with it by distracting the public with his "peanut jig."

    Jeremy 
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"BALALALALALALALALA-"
Voiced by: Michael Cusack
Charlie's only form of hellish entertainment when he is sent to Hell.
  • Animation Bump: Gets suddenly smoothly animated when Charlie does punch him for getting in his way.
  • Brick Joke: Charlie threatens to punch him if he "entertains" him again, and sure enough, he pops out of nowhere to "entertain" Charlie halfway through the episode, causing the latter to follow through with his threat to punch Jeremy. He also appears yet again to pay Charlie back for punching him earlier by clocking him in the face.
  • The Dog Bites Back: Returns Charlie punching him back when Satan puts him through proper torture.
  • Even Evil Has Loved Ones: He comforts the imp who introduces Charlie to hell when the latter makes him cry while glaring angrily at the newly arrived critter, and overall seems to be on good terms with him.
  • Limited Animation: He's animated in an extremely fast fashion with only two frames of animation for him "entertaining" Charlie, aside from him flailing his tounge. Subverted when he gets punched by Charlie, as he suddenly becomes both smoothly and realistically animated, as he slumps to his knees while trying to hold himself up with a hand.
  • Incredibly Lame Fun: He's supposed to entertain Charlie by repeatedly flailing his hands in his face while making rapid, high-pitched babbling noises which Charlie reasonably treats as being more annoying than anything. The nature of the "entertainment" he provides is somewhat justifiable, considering that he's an inhabitant of Hell and presumably meant to torment Charlie instead of providing him with any actual fun.
  • Poke the Poodle: For Hell standards, having a demon just flailing his arms in front of your face while yelling is more petty than anything.
  • Rule of Three: He makes a total of three appearances in "Charlie Dies and Doesn't Come Back", the first one when he's introduced to Charlie by the imp, the second to appear out of nowhere to "entertain" Charlie and getting punched by him for his troubles, and then making his third and final appearance to punch Charlie as payback.
  • The Speechless: He never says a word, and only makes a rapid, high-pitched babbling noise, as well as groaning in pain when Charlie punches him.
  • Sudden Anatomy: He gains another finger when he returns to punch Charlie as payback for getting punched by him before.
  • Too Dumb to Live: Downplayed. He continues to "entertain" Charlie yet again despite Charlie warning him that he's gonna punch him if he does it again, and winds up getting punched for his troubles, indicating he isn't particularly intelligent.
  • Torment by Annoyance: All he does is annoy Charlie.

    Charlie's Grandma 
https://static.tvtropes.org/pmwiki/pub/images/screenshot_2022_01_14_123618.png
"MORE FOR ME! AH-HAHAHA!"
Voiced by: Zach Hadel
Charlie's deceased grandmother, who currently resides in Hell.
  • Cool Old Lady: From what little we see of her, she seems to be one. She seems to have a good relationship with Charlie and she is the one who helps him find Satan.
  • Easy Road to Hell: If her reason for being in Hell is commonplace, there's not going to be a lot of people in Heaven.
    Charlie: Grandma? What are you doing here?
    Grandma: Oh, I cursed and said DAMN in 1958 when I saw your grandfather getting shot in the head by that ROTTEN burglar.
    Charlie: That seems a little bit unreasonable, I don't think you should be in Hell for that.
  • Gag Nose: With her long nose and wrinkly face, she looks like a worm.
  • Jabba Table Manners: The way she eats the lollipop she offered defies any description other than "aggressive fellating". Even Charlie can only back away slowly.
  • Large Ham: To say that she talks in a dramatic and over the top fashion would be an understatement.
  • Loon with a Heart of Gold: She's certainly a space case, but she has an incredibly sweet personality, given that she's overjoyed to see Charlie and immediately helps her grandson out when he asks her for directions.
  • Mythology Gag: Elements of her appearance, such as her Gag Nose and her milky eyes, as well as her habit of doing an occassional Wild Take with her eyes as she speaks, are similar to the titular character from "Father's Jewel", an animated short made by Zach before he made Smiling Friends.
  • The Pollyanna: For someone trapped in Hell, she seems pretty chipper.
  • Posthumous Character: Died before the start of the show, apparently due to peanuts.
  • Suddenly Shouting: Has a habit of shouting certain words, accompanied by a little Wild Take every time she does it.
  • Sweet Tooth: Offers Charlie a scrrrrumptious lollipop before he descends further into Hell. When he refuses it, she goes to town on it.
  • Verbal Tic: She begins almost every sentence with "Oh!"

    God 
https://static.tvtropes.org/pmwiki/pub/images/godsmilingfriends.png
"A deal's a deal!"
The Christian god Himself, and the arch enemy of Satan. He doesn't appear until the end of "Charlie Dies and Doesn't Come Back" to not only rescue Charlie from being tortured by Satan, but also brings him back to life after Charlie apparently learns his lesson by making Satan smile.
  • Actor Allusion: This isn't the first time that Gilbert Gottfried has voiced an all-powerful being, although he's voicing a much nicer one this time.
  • Deus ex Machina: He rescues Charlie from Satan's grasp.
  • The Faceless: His face is obscured by a blinding light. Assuming that isn't His face, anyway.
  • God Is Good: He rescues Charlie from Hell after he's learned his lesson.
  • Heroic Build: He's built like a Greek god and swiftly rescues Charlie from Hell after he learns his lesson while praising him for doing so on the way out.
  • Large Ham: Take Gilbert Gottfried's usual hamminess and cast him in the role of God, and this is what you get.
  • Light Is Good: His head is obscured by a blinding globe of light and He also dresses in a gold colored toga, and is overall shown to be a benevolent and fair god, rescuing Charlie merely seconds after He deems the critter has learned his lesson as he's being tortured by Satan, and also resurrects him as well.
  • Nice Guy: Saves and resurrects Charlie, and overall comes across as being pretty friendly in the short amount of time He does so.
  • Vocal Dissonance: Gilbert Gottfried's infamous voice coming out of God would already count, but as if that wasn't enough it's also coming out of a version of God who's absolutely ripped.

    Brazilian Man 
https://static.tvtropes.org/pmwiki/pub/images/brazilian_man.png
"But are you a-you are a tourist?"
Voiced by: Marc M.
A man encountered by the Smiling Friends at the airport on their vacation to Brazil. Really interested in whether or not they're tourists for some reason.
  • Ambiguously Evil: While he doesn't do or say anything overtly threatening, there's something decidedly off about him that unnerves the Smiling Friends, mainly his rather creepy interest in whether or not that the Smiling Friends are tourists. Charlie in particular flinches when the man points at him because he thinks the man is going to hit him or pull out a weapon.
  • Ambiguous Situation: It's unknown whether or not he's some sort of gangster in a scheme to rob tourists of their money, a lone wolf con-man, or simply in dire need of cash and coming across as being socially awkward and creepy.
  • Con Man: Seems to be a very poor one. His idea of a con appears to be awkwardly approaching people and asking them for cash.
  • Funny Foreigner: Downplayed. He isn't an outwardly comedic character, but he's still a source of comedy due to the extreme awkwardness of his interaction between the Smiling Friends.
  • Giving Someone the Pointer Finger: Does this repeatedly when speaking to Charlie.
  • No Sense of Personal Space: Doesn't think twice about invading people's personal space by repeatedly pointing in their faces.
  • Shout-Out: His fixation on the Smiling Friends giving him cash might be a reference towards an old webcomic that made fun of annoying Brazilian players on online games, especially ones that go on servers for other regions.

Season 2

    Count Groxia 
Voiced by: Joshua Tomar
Formerly the main villain of the Gwimbly games, Count Groxia now lives a normal life with a wife and children. Gwimbly, Pim and Allan try to get him to reprise his role for a new game, but he rejects the offer.
  • Accessory-Wearing Cartoon Animal: In his boss fight in Gwimbly, Count Groxia appears to only wear a cape, gloves and boots. Averted in the modern day, where he's dressed like a typical white-collar worker.
  • Animated Actors: Like Gwimbly, he's a video game character who lives in the real world, and has since moved on and gotten a normal job.
  • Attack Its Weak Point: His stomach is completely green while the rest of his body is purple, and Gwimbly punches it during his boss fight, which ends up dealing damage.
  • Cartoon Creature: Like Gwimbly, it's not clear what he is.
  • Fat Bastard: Count Groxia is the main villain of the Gwimbly games who is also rotund and heavy enough that he has a Shockwave Stomp attack. Of course, that's just his character in the games.
  • Mean Character, Nice Actor: He might have played the villain the Gwimbly games, but he's a perfectly normal guy in real life with a wife and children. Even though he rejects the offer to be in the next Gwimbly game, he's polite about it, and at least considers letting Gwimbly crash on his couch before his wife shoots down the idea. He also has a son and daughter that he dotes on.
  • Non-Standard Character Design: Like Gwimbly, he's animated as a low-poly 3D character from a 90's platformer.
  • Shockwave Stomp: He did this in his boss fight. Gwimbly would avoid it by grabbing onto Mr. Millipede.
  • White Collar Worker: He's shown wearing a white collared shirt and tie, implying he has this sort of job.

    Mr. Millipede 
Gwimbly's trusty sidekick who would always help him fight Count Groxia. In the present day, he's died of a fentanyl overdose.
  • Dead Sidekick: He was Gwimbly's partner, but is now deceased.
  • Elephant in the Living Room: Apparently, no one was willing to speak up about America's fentanyl crisis during his funeral.
  • Four-Legged Insect: At first glance, he doesn't seem to to have the wrong amount of limbs, in his case he six like most bugs. The only problem is that millipedes have more then just six limbs.
  • Funny Animal: Unlike Gwimbly and Count Groxia, whose species are both hard to decipher, Mr. Millipede was an anthropomorphic millipede.
  • Hover Board: He used one to fly around and help Gwimbly out.
  • Posthumous Character: Is already gone by the time the episode starts.

    Bill 
Voiced by: Hans van Harken
One of Pim's UFO hunting buddies.
  • Conspiracy Theorist: In comparison to Filmore, he's considerably more sane when it comes to his beliefs.
  • Shout-Out: His voice and inflection is a direct reference to Peter Griffin's from Family Guy.
  • They Would Cut You Up: When Pim and Charlie wake up, Bill's stomach is cut open and his innards are visible.
  • Token Human: The sole human in Pim's UFO hunting group.

    Filmore and Duncan 
Filmore voiced by: David Firth
Duncan voiced by:
Two of Pim's UFO hunting buddies. Filmore is a lanky bug-eyed critter with frazzled hair who has a penchant for conspiracies whereas Duncan is a chubby critter with blonde hair.
  • Big Eater: When Pim is introducing his friends to Charlie, Duncan's shown eating all the snacks they brought.
  • Conspiracy Theorist: And how. Filmore believes the Earth is flat and protected by a glass dome.
  • Early-Bird Cameo: They both appear in "A Silly Halloween Special" attending the costume party, they later makes a cameo in "Gwimbly" on the thumbnail of a video.
  • Horror Struck: Upon Charlie's successful summoning of the UFO, Filmore genuinely freaks out as he was just rambling beforehand and didn't believe the aliens were real.
  • Pyromaniac: Filmore can be seen excitedly lighting a piece of paper on fire during his introduction shot.
  • The Voiceless: Duncan doesn't speak at all during his time on screen.
  • Vomit Indiscretion Shot: When asked what he thinks about aliens, Duncan throws up the animal cookies he ate earlier.

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