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    In General 
Our titular charity and the stars of our show. They're a 5-man organization led by an eccentric man known as "The Boss" founded for the purpose of spreading a little happiness to the world, and the other four workers of the main duo, the optimistic little critter named Pim and his friend, Charlie, as well as Glep, a mysterious little character who seems to just hang around, and the unemotive lankster Alan, the office manager who maintains the building they operate out of.
  • The Ace: The organization always makes their client smile, no matter what... even if it's not entirely through their own efforts. The fact that they manage to have such a high success rate in spite of their contrasting personalities says a lot about how capable they are.
  • Big Guy, Little Guy: Two separate duos, Charlie and Pim as well as Allan and Glep.
  • Cartoon Creature: Aside from Mr. Boss (presumably), they are clearly not human, considering that actual humans exist within this setting, but it's hard to tell what they are supposed to be.They have technicolor skin, with Charlie being yellow, Pim being pink, Alan being red, and Glep being green. With the exception of Pim, they have unusual body types, with Charlie having a semicircular head that curves into the rest of his body, Alan having abnormally long arms and legs, and Glep being incredibly small, having eyes on the sides of his head, and lips that jot out from the rest of his body. Pim also mentions that the little strand of hair on his head isn't hair at all, but rather, is an exposed nerve ending, and that he played Gwimbly's games when he was "a little tadpole".note 
  • Cynic–Idealist Duo: Pim is the idealist as he always has an upbeat attitude and tries to see the best in everyone. Charlie and Alan are the cynic, Charlie tries to be more levelheaded and realistic compared to Pim, whereas, Alan just wants to get the job done and finish it as soon as possible. This is eventually deconstructed in "Charlie Dies and Doesn't Come Back", where Charlie and Pim eventually argue with each other about how their respective attitudes affect the other; Charlie believes that Pim forces people to be happy, no matter how right they are to be upset. Whereas, Pim believes Charlie's attitude is unhelpful because they're trying to help people smile and believes that Charlie has to be motivated to do his job.
  • Does This Remind You of Anything?: Despite their job supposedly being simply just making people smile, a lot of the tasks they end up with, such as helping Desmond cheer up so that he doesn't kill himself make them similar to crisis workers.
  • Oddly Small Organization: They're a charity that's profitable enough to be able to ENDURE losing $2.4 billion, as shown in "Frowning Friends", yet there are only five of them, and their headquarters is just a homely little office building.
  • Peace & Love Incorporated: Subverted. Their leader, Mr. Boss honestly DOES want to make people smile, and Pim and Charlie are both genuine and sincere in their job as well, even if the latter is rather lazy and mildly cynical.

    Pim 

Pim Pimling

https://static.tvtropes.org/pmwiki/pub/images/2020_04_04_13_0.png
"We don't always get along, but we sure do love each other!"
Voiced by: Michael Cusack
An eager employee of the Smiling Friends.
  • Badass Adorable: The very fact that this little guy has gone through so much dangerous and scary scenarios and yet still (more often than not) keeps up his optimistic and positive attitude can have him count as such.
  • Beware the Nice Ones: Despite being legitimately nice to pretty much everyone, Pim is by no means immune to anger if provoked or agitated enough. "Enchanted Forest" is probably the most notable example.
  • Big Guy, Little Guy: The Little Guy to the taller Charlie.
  • Blind Without 'Em: Played with in that he hasn't worn glasses since he was young, but his eyesight doesn't seem to have improved; in one episode, he mistakenly eats a bowl of earthworms complete with earth instead of peanuts, and manages to confuse an 8 with a 3 at the worst moment possible.
    Charlie: You really need to get your eyes checked.
  • Body Horror: That singular strand sticking out of his head isn't hair but rather an exposed nerve ending. It’s especially more terrifying when you realize when Mr. Frog pulls his "hair", it hurts way more than you think.
  • Butt-Monkey: Despite his idealism and goal to share it with others, Pim seems to get the short end of the stick a lot. Throughout the entire pilot we see him get worn down by attempt after attempt to make Desmond smile until he's a literal husk by the end of it. Then in the series proper, he falls in love with "Shrimpina" until she falls in love with Shrimp instead, he ends up on the sidelines in the Enchanted Forest until he goes mad with jealousy seeing Charlie do all the quests he's always wanted to do, and he almost gets murdered by the Forest Demon in the Halloween Special.
  • Character Tics: Giving people affectionate little pecks; in the first season alone, he does it to Desmond, the Century Egg, his imagined future version of "Jennifer", and a random bird.
  • Charlie Brown Baldness: Subverted - Pim is just regular-style bald, and his single "hair" is a nerve ending standing straight up from the top of his head.
  • Cheery Pink: Pim is a pint-sized bundle of joy who has a pinkish skin tone.
  • Continuity Nod: Pim wore glasses when he was much younger, as shown in his Enchanted Forest flashback. However, at his current age in the show, Pim has stopped wearing glasses. This ties into the continuity established a few episodes earlier, where Charlie repeatedly insisted Pim needed to get his eyes checked.
  • The Cutie: He's a tiny little fella with a cheerful and idealistic mindset who is kind and considerate to virtually everybody he meets.
  • Deconstructed Character Archetype: Of The Idealist. Pim genuinely wants to help people with their problems, but they're often too complex or deep-seated for him to realistically fix. Especially considering his simplistic methods of trying to cheer people up, like thinking taking Desmond - a suicidally depressed man - to a party or an amusement park will immediately make him feel better. Desmond even lampshades it when Pim brings him to lunch with his breathtakingly dysfunctional family.
    Desmond: ...Is this supposed to make me not want to kill myself?
  • Everyone Has Standards: There are a few occasions where even Pim's Wide-Eyed Idealist views and enthusiasm have their limits.
    • He's clearly disturbed by Mr. Frog's violent and Ax-Crazy tendencies, and appears ready to write him off as a lost cause after Mr. Frog seemingly kills his career once and for all for his comments to Jimmy Fallon on The Tonight Show.
      Pim: (to Charlie) Um... that was, uh... That was really bad.
    • Episode 1 of Season 2 shows that even he wouldn't pay 5 dollars just for his childhood idol to do a 1-2 second dance.
  • Expressive Hair: His strand wiggles a bit when he introduces himself. Maybe Justified given that it's actually a nerve ending, and would be connected to muscle rather than a follicle.
  • Extreme Doormat: Pim is occasionally shown to be timid and unnecessarily apologetic to people, namely his sister and the frat members he attempts to make friends with.
  • Fatal Flaw:
    • Naivity. Although Pim tries to help clients smile again, clients like Desmond show that these problems are too complicated and deep-rooted for him to realistically fix. As shown by how Pim thought he could help Desmond by taking him to an amusement park, despite the latter showing that he was on the verge of shooting himself.
    • Selfishness. Although Pim is very selfless and altruistic, it is shown multiple times that Pim often tries to resolve issues by himself rather than heed warnings or accept that not everyone is as idealistic as him. In his argument with Charlie, Charlie makes a point that Pim forces people to be happy and tries to phrase his arguments as if everyone is affected by Charlie's attitude when it was just Pim affected by it. Despite Charlie telling Pim that he thinks Desmond has already chosen to kill himself, Pim still tries to help Desmond but it instead makes Pim similarly depressed.
  • Four-Temperament Ensemble: The Sanguine; an enthusiastic, optimistic fellow who takes pride in his occupation in spreading happiness to everyone around him.
  • Friend to All Children: He's eager to help children out, but he doesn't quite know how to properly phrase his enthusiasm.
    Pim: "This is gonna be great, Charlie! I love helping kids! I love kids, Charlie! I LOVE KIIIIDS!"
    Charlie: (Looks around nervously) "Uh, Pim, I—I would really not be, uh, screaming that at the top of your lungs."
  • The Fool: He always manages to help his clients, in spite of his own incompetence.
  • Genki Guy: He's enthusiastic to get the job done and put a smile on anyone's face.
  • Gleeful and Grumpy Pairing: An optimistic, eager-to-please Cheery Pink Keet compared to his co-worker, the grouchy and blunt Charlie.
  • Gosh Dang It to Heck!: Played with. He's one of the few characters that doesn't swear, even in situations where it would be deemed understandable. The closest thing he belts out to a swear is an enthusiastic "Eff, yes!" at the start of "Shrimp's Odyssey". That being said, he's perfectly fine with exclaiming blasphemies during shocking or stressful situations, and he does utter a couple of "Dammit's" in the Brazil special, but he still tries his best to keep a clean tongue.
  • Green-Eyed Monster: In "The Enchanted Forest", he gets aggressively jealous of Charlie's fun adventures with Mip, to the point where he regresses into a Gollum-like creature.
  • Hartman Hips: An unintentional example thanks to the art style since he clearly meant to drawn as chubby, but he can be viewed as having these.
  • Heroic BSoD: Implied, considering the face he makes at the end of the pilot. He gets better.
  • Idiot Hair: His exposed nerve ending replicates the look of one.
  • Keet: He's a colorful, hyperactive, and sweet little guy who's very fond of helping people in need.
  • Land Down Under: He speaks with a slight Australian accent, the natural accent of his voice actor. His parents (also voiced by Cusack) speak with much thicker accents. That coupled with flashbacks showing the young Pim living in the same town as he does in the present suggests that the family immigrated from Australia when Pim was a small child.
  • Living Mood Ring: His physical form seems to actually alter somewhat in accordance with his current mood. In both the pilot and "Enchanted Forest", his skin tone goes completely gray after he spends an extended period of time being upset. He actually becomes a Gollum-esque creature in the latter episode when his jealousy towards Charlie and Mip reaches its peak, only to immediately revert back to his normal form when his fight with Charlie accidentally gets Mip killed.
  • Manchild: While definitely more mature than most examples, he has a childlike and energetic disposition that goes hand-to-hand with an idealistic worldview.
  • Nice Guy: At the end of the day, Pim genuinely wants to help people, and he's very enthusiastic about it.
  • Not So Above It All: Pim may be an optimistic Nice Guy, but even he's not above succumbing to bitter jealousy, as seen when he and Charlie visit the Enchanted Forest and Charlie gets to go on the kinds of quests that Pim has always wanted to.
  • Older Than They Look: Despite looking and behaving like a child, he's old enough that a group of frat kids mock him over it. In the commentary for the Enchanted Forest episode, Michael Cusack states that Pim is 33 and Charlie is 27.
  • The Pollyanna: He always tries to find the silver lining in everything, no matter how dire the situation for his clients may be.
  • Repetitive Name: "The Smiling Friends Go to Brazil!" reveals that his full name is Pim Pimling.
  • Right for the Wrong Reasons: Promises Desmond that he'll have a "big smile on his handsome face" at the end of the day. Desmond DOES end up with a big smile on his face, but it came from finding a new purpose in his life, with Pim's efforts contributing nothing.
  • Screams Like a Little Girl: Pim does this in "A Silly Halloween Special" after he gets shoved away by lightning in the forest.
  • Secretly Selfish: While Pim is a genuinely good person, he does have the occasional spout of selfishness shown in "Shrimp's Odyssey" and especially in "Enchanted Forest."
  • Sensitive Guy and Manly Man: The Sensitive Guy to Charlie's Manly Man, who prefers to deal with clients in a friendly, compassionate way.
  • Sharp-Dressed Man: Wears a white button-up shirt with belted trousers.
  • Sphere Eyes: Has big, round eyes, one slightly larger than the other.
  • Yellow/Purple Contrast: The purple to Charlie's yellow.

    Charlie 

Charlie Dompler

https://static.tvtropes.org/pmwiki/pub/images/2020_04_04_13_51.png
"What's happening, big guy? What's with the gun?"
Voiced by: Zach Hadel
A more cynical and realistic employee of Smiling Friends.
  • Ambiguously Christian: He's shown wearing a cross necklace while in Mr. Frog's jacuzzi, but otherwise doesn't show any signs of being religious aside from referring to murder as violating the sixth commandment note 
    • Eventually revealed to be Catholic in the commentary for “Mr. Frog”.
  • Audience Surrogate: To a point. His reactions to the absurd and often outright insane situations the Smiling Friends get themselves in are often more realistic than his compatriots'. For example, during his foray into Hell, he is accosted by a creature that waves its fingers in his face and screeches at him; after warning him once not to do that again, he punches the creature the next time they meet and he does that despite his warning.
  • Back from the Dead: In the season finale, he dies a horrible death from getting crushed by a tree. He gets better.
  • Berserk Button:
    • Charlie's normally a very chill guy who at best gets annoyed or disturbed by things; he rarely if ever shows actual anger. But invade his personal space like Jeremy the entertainment devil does, and he will get violent for the only time in the show.
      Charlie: Dude, if you do that again I'm gonna punch you, I'm not kidding.
    • Charlie's normal composure tends to take a hit when he has to do extra, unnecessary work to get things done. When he and Pim get captured by a witch and wind up miles from the princess' castle he actually yells about the situation. And his poor mood in the Christmas Episode is because he has to work on Christmas Eve.
    • Though it's only shown once, implying he doesn't do any work appears to set him off, as Pim saying that he has to pull Charlie's weight causes Charlie to (unwittingly) kick off the plot of Charlie Dies And Doesn't Come Back by causing a tree to fall on him as he's angrily swinging at it with an axe.
      Charlie: Pim, I'm just helping out, something that I never do according to you! Does this put anyone in a- bad mood? Does this put anyone in a bad mood-?!
  • Big Guy, Little Guy: The Big Guy to the smaller Pim.
  • Black Bead Eyes: His eyes are just a pair of black dots.
  • Brutal Honesty: He's often pretty blunt when he tries to get his point across, and not always so tactful.
  • Brilliant, but Lazy: He's really not into his job, but he's still a part of the Smiling Friends for a reason; he's perfectly capable of doing what he's paid to do when the chips are down, to the point where he even cheered up Satan himself.
  • Butt-Monkey: Like his buddy Pim, Charlie has had his share of misfortune such as getting kicked in the shin in the climax of "Frowning Friends", suffering side-effects from Mip's potion in "The Enchanted Forest" and in the Season One finale, literally dying and going to hell, let alone letting himself get the crap beaten out of him by the demons there just to make Satan smile.
    • This continues into the season 2 premiere, where James forces Charlie to do things such as dress up like a French maid and bake him a casserole. And then his nose gets ripped off by James while Charlie pleads for him to smile and put him out of his suffering.
  • Crouching Moron, Hidden Badass: He's pretty capable on the rare occasions he can get motivated enough to do anything, managing feats like ending the thousand-year war between The Greys and the Giant Spiders and reaching the deepest depths of Hell on foot. In one thirty-second montage alone he kills a dragon, rescues mermaids from a trap, traverses a lava pit, and kills a medusa-esque monster.
  • The Cynic: Charlie plays this role in the show in contrast with Pim as elaborated on below. He's at the very least jaded enough that when the Frowning Friends deploy a film of humanity and the world being full of bastardry, he finds it too mild to react.
    Pim: Don't look, Charlie!
    Charlie: ...is this really supposed to be- I mean, I've seen way worse stuff than this on the internet, I don't-
  • Deadpan Snarker: With heavy emphasis on the deadpan.
  • Deconstructed Character Archetype: Just as Pim is a deconstruction of The Idealist, Charlie is a deconstruction of The Cynic. He's often the first to shoot down Pim's more whimsical approach to helping their clients, and reacts to any extra effort he suggests putting into their assignments with annoyance. Rather than making him the wiser and more effective of the duo, this attitude results in him being incredibly lazy and unhelpful, with the few times he does make an effort turning out to be just as misguided and ineffectual as Pim's, just for different reasons. Pim finally gets fed up with his attitude in the finale, pointing out his constant negativity makes him emotionally exhausting to be around since everyone else has to put in the extra effort to counteract it.
  • Delayed Reaction: It takes him until James stops talking after he rips his nose off to scream in pain.
  • Demoted to Extra: The first episode of season 2 has him relegated to the B-plot whilst Allan takes his place.
  • Don't Ask: Once he's brought back to life after going to Hell, he says a variation of this.
    Pim: Charlie! How is this possible?
    Charlie: Look. I can barely explain the nutty adventure I've just went on... So I'm not going to-I don't-I don't wanna talk about it. [beat] I've seen the Devil.
  • Early Installment Character-Design Difference: A subtle example. Throughout the pilot, whenever Charlie faced the camera straight on, his hair didn't appear to be visible. This video compilation for the first season shows how this was changed from the second episode on so that his hair is always visible from the sides of his head whenever he's directly facing the camera.
  • Everybody Has Standards:
    • Just because he hates it when fast food restaurants make healthier food he doesn't think it justified to break the Sixth Commandment over it.
    • He may have been perfectly okay mooching off Mr. Frog's fortune when they were helping him, but during "The Smiling Friends Go To Brazil" as soon as Pim suggests trying to rope Mr. Boss into covering their hotel expenses Charlie is visibly uncomfortable with the idea and immediately shoots it down.
  • Fantastically Indifferent: He has his moments. His reaction to several partygoers mistaking a demon's appearance for blackface, and ripping it to pieces and eating it alive is to nonchalantly mention that this is exactly why he doesn't bother dressing up for Halloween.
  • Fatal Flaw: Charlie's downbeat attitude makes him ill-equipped at helping to cheer people up, often relying on Pim to fo the actual work while he hangs back and enjoys the perks of the job. Whenever he's forced to do his job alone, Charlie's flaws are all the more glaring. He's unable to give Satan any guidance without making it sound judgemental and when he finds out Satan Can't Take Criticism he just doubles down and escalates the situation.
  • Four-Temperament Ensemble: The Phlegmatic; practical and cool-headed in personality, though bordering on laziness at times since he's not as passionate as Pim is at their job.
  • Gag Nose: It's quite prominent, and makes up a good portion of his head (especially apparent when seen from behind and over his shoulder.)
  • Gleeful and Grumpy Pairing: He's deadpan, cynical and less-than enthusiastic over his job, compared to his co-worker Pim.
  • The Grinch: Is described as this in the opening narration of the Christmas Episode, though his grouchy attitude was more due to having to work on Christmas Eve than a dislike of Christmas in general.
  • Hypocrite: His pep-talk about how Shrimp needs to get his life together so that women will find him attractive is interrupted midway through by him loudly coughing up phlegm hard enough for his stomach to pop out underneath his shirt.
  • Ink-Suit Actor: Caricatures of Zach Hadel made by his friends and himself often exaggerate the nose due to his nasal voice, all of which have been adapted into Charlie's character. Charlie also isn't able to handle James when he displays psychopathic tendencies and just folds to his whims without trying to quietly guide James into an acceptable compromise.
  • Jerkass Has a Point: While he's usually a lazy douche, his advice is generally more practical than Pim's on the few occasions that he does actually try to do his job. He points out that Desmond is already suicidal and is likely a lost cause to them, that Shrimp should move on from Shrimpina and focus on getting his life together, and that they should focus on their assignment in the Enchanted Forest and not get sidetracked by questing. Unfortunately, his advice is rarely heeded, and on the occasions he is able to act on it he proves to be just as out of his depth as Pim is.
    • He also points out that what they do is a Job, and can't or don't have to help unless asked for. Gwimbly was on hard times and Pim wanted to help him, but Gwimbly never actually asked for their help at any point, thereby making Gwimbly's predicament none of their business. He only really got help because Pim's loved his games and is dedicated to his work, and Allan simply wanted him gone from their lot. Charlie doesn't stop them, but he didn't help them either, following company policy, which does bite him in the ass not to long after.
    • Although slightly subverted in Desmond’s case. He does immediately recognize that they’re out of their depth in dealing with a man literally on the verge of suicide. However, rather than shifting responsibility to proper care-workers who could help him, he advises to Pim that they should just drop the job and leave Desmond to kill himself.
  • Jerk with a Heart of Gold: Cynical as he may be, he seems to genuinely value his friendship with Pim and is shown as happy whenever the Smiling Friends actually do manage to help a client.
  • Know-Nothing Know-It-All: His pointers to Shrimp for squatting at the gym are dangerously wrong. When another patron tries to give Shrimp genuinely helpful advice on how to properly position himself, Charlie shoos him away and tells Shrimp to ignore everything he said. It predictably ends with Shrimp dropping the barbell and injuring himself.
  • Know When to Fold 'Em: Quickly saw Desmond as a lost cause, and knew he couldn't be much help for him. Although, it may have been his lethargy talking.
  • The Lancer: Accompanied by Pim on their jobs, he attempts to reel in his coworker's naïveté.
  • Naked on Revival: He is nude when brought back to life in the season one finale.
  • Nominal Hero: Downplayed. He's not really a bad guy, but doesn't really care that much about helping people.
  • Not So Above It All: While he is the Only Sane Man among the more colorful personalities at work, whenever he actually tries to help others his efforts go no better than Pim's tend to.
  • Only Sane by Comparison: Downplayed. He's mostly sane, but Pim accurately points out the fact he refuses to do his job out of apathy and cynicism makes him a terrible employee, and that for as eccentric as everyone else is, they at least try to do their jobs to the best of their ability.
  • Only Sane Man: Along with being The Cynic, he often plays the straight man during the absurd situations around them, and has no issue pointing it out. And on the occasion that he isn't cynical or lazy, his advice is actually quite practical and down-to-earth as opposed to Pim's more optimistic but ultimately naïve and reactionary solutions. Though just like Pim he rarely has the expertise to successfully act on his suggestions.
  • Our Homunculi Are Different: He mentions that he's been going to Salty's ever since he was a homunculus. It's unknown if he was actually a "proper" homunculus, or it's just his way of saying that he was a child.
  • Properly Paranoid: He doesn't want to dress up for Halloween because he has seen people being cancelled for wearing offensive Halloween costumes. The death of the Forest Demon only vindicates his concern, as he nonchalantly asserts his position as Pim stares in horror at the brutal execution of his pursuer.
  • Punch-Clock Hero: It's heavily implied Charlie's Only in It for the Money, and he doesn't really care about doing his job.
  • Seen It All: At least in regards to internet videos, he's been entirely nonchalant when presented with an Atrocity Montage because he's seen way worse online. And he comments rather nervously after an encounter with a suspicious Brazilian man that he's seen some fucked up things coming specifically from Brazil that way. All in all, this paints him as someone that's browsed LiveLeak and similar sites a little too long.
  • Sensitive Guy and Manly Man: The Manly Man to Pim's Sensitive Guy, who prefers to handle clients in a blunt, matter-of-fact style.
  • Serious Business: Salty's, a fast food joint he's been eating at ever since he was a homunculus. When told that the salty burger was removed from the menu, he immediately decides to speak to the owner, Simon S. Salty, directly, a far cry from how lazy and dispassionate he usually is. And at the end, he's willing to travel all the way to China and drag everyone along for the funeral to fulfill Century Egg's last request, something that is almost unthinkable of Charlie otherwise.
  • Sincerity Mode: When he agrees to fulfill the Century Egg's inconvenient last request, the delivery is absolutely dripping with sarcasm. However, it turns out he was being completely genuine and is ultimately true to his word.
  • The Slacker: Once he let Pim take the lead, he couldn't come up with a single idea to help Desmond. Charlie also doesn't seem to be in much of a hurry to save Mr Frog's reputation once he figures out that the length of this assignment will allow him to mooch off the disgraced celebrity.
  • Small Name, Big Ego: He unironically considers himself an Alpha Male, as he tells Shrimp when he takes him to the gym (and gets him horribly injured out of sheer ignorance).
  • Straight Man/Only Sane Man: Probably the most normal employee out of the business.
  • Sudden Anatomy: He normally has Black Bead Eyes, but whenever he's sufficiently shocked or stunned enough, he gets drawn with visible sclerae to illustrate the magnitude of these feelings.
  • Yellow/Purple Contrast: The yellow to Pim's purple.

    Allan 

Allan Red

https://static.tvtropes.org/pmwiki/pub/images/2020_04_04_20_6.png
"Glep, did you take a paper clip? I counted seventy-four last time, and now there's only seventy-three."
Voiced by: Michael Cusack
Charlie's and Pim's meticulous co-worker.
  • Accent Upon The Wrong Syllable: He usually enunciates his speech very deliberately and tends to put extra emphasis on hard consonants that most other speakers would soften (Dirty brown water, spraying).
  • Accessory-Wearing Cartoon Animal: Wears nothing but a blue necktie. Word of God notes this isn't strange at all for Critters.
  • Big Guy, Little Guy: Is the tallest of his coworkers, and the stark opposite of the diminutive Glep.
  • Berserk Button: Don't startle him or he'll kick you in the face.
  • Cloudcuckoolander: Zig-zagged. He generally acts weird and is lost in his own world, but the moment he encounters an even weirder situation, he acts more normal. After he gets out of such a situation, however, he becomes weird again.
  • Cold Ham: He gives a Heroic Vow to hunt down whoever took his cheese from the fridge, in as deadpan of a tone as he always does. He barely even raises his pitch when he laments his crucifixion.
  • Color Contrast: Solid red with a blue accessory. Plus, makes a Red/Green Contrast with Glep.
  • Creepy Long Fingers: He has a good set of thin ones on him.
  • A Day in the Limelight: Leads the B-plot in "Desmond's Big Day Out". He also replaces Charlie in the A-plot with Pim in "Gwimbly: DREEEDX4K (ADC)."
  • Demoted to Extra: You'd be excused for thinking Alan might be the Deuteragonist to our two leads based on the pilot, as he leads the B-plot there. But that's the only time he does so in Season 1. This trope is heavily downplayed though as Alan's still a member of the main cast, and the only reason the trope comes into play is because his focus episode is the very first one.
  • Determinator: No one takes Allan's precious piece of cheese and gets away with it.
  • Don't Sneak Up on Me Like That!: During his visit to IGBG, he's addressed by an inches-high receptionist and his first instinct (probably thanks to residual trauma from the Bliblies) is to kick her in the face as soon as he finds where the voice is coming from, claiming she "startled" him.
  • Face–Heel Turn: Joins the Frowning Friends simply because they have a better 401K plan. He leaves later.
  • Four-Temperament Ensemble: The Melancholic; studious and analytical; would rather avoid expressing his emotions.
  • Impaled Palm: The bliblies crucify him.
  • Jerk with a Heart of Gold: Zig-zagged. He's mostly cordial with his coworkers, but comes off as rather amoral.
  • Jerkass to One: Normally he's cordial enough, but he treats Gwimbly rather dismissively, spraying him with dirty brown water to get him to leave and only stopping to help because his arm got tired of it, and constantly trying to find an easy way out of helping him smile afterwards, even to the point of asking if he can just sleep at Mr. Millipede's grave so he and Pim can leave. After everything's said and done he's more happy that he doesn't have to spray him anymore than him making a comeback.
  • Not So Above It All: Seems grumpy and uptight throughout the episode, but laughs with Charlie and even playfully gives his nose a gentle bite while making nom noises at the end. He also reacts with the same genuine fear and confusion to the 3D alien popping out of the TV as Charlie and Glep.
  • Obsessively Organized: He keeps an individual count of the paper clips in the break room.
  • Punch-Clock Hero: Whatever his job is at the office, it becomes clear with Gwimbly that he's not very excited to actually go on the field and help people smile like Pim.
  • Straight Man: To the squatter who lives in the walls. He generally has a tendency to get shoved into the role whenever someone weirder than him comes along.
  • Token Evil Teammate: Somewhat. He comes off as the most amoral and cruel of the Smiling Friends, particularly in the Season 2 premiere, where he abuses Gwimbly for being homeless and sleeping outside their office, and kicks a Secretary in the face for startling him.
  • Trademark Favorite Food: Cheese, given that the entire reason he winds up searching through the office is that his piece of cheese is missing, and given how the Boss tells him to go find some cheese when he catches him in the middle of a conversation with his hallucinations is any indication.
  • Trauma Button: Little people are implied to be this for him in the Season 2 premiere, likely as a result of his treatment at the hands of the Bliblies, as his immediate response to a small secretary startling him is to kick her in the face.
  • Vocal Dissonance: For some reason, his voice when crying out in pain or surprised fear is much deeper.
  • White Collar Worker: Seems to stay and work from the office.

    Glep 

Glep

https://static.tvtropes.org/pmwiki/pub/images/2020_04_04_3_1.png
Voiced by: Zach Hadel, Joshua Tomar (Elderly Glep)
A mysterious creature who also happens to work at Smiling Friends.
  • Accessory-Wearing Cartoon Animal: He is basically a small, seemingly lizard-like critter that wears a purple wizard hat that's two-thirds of his own height.
  • Big Guy, Little Guy: The impishly small counter to the lanky and lean Alan.
  • Button Mashing: His tactic of choice while playing fighting games, which apparently works in his favor, according to Alan.
  • Bratty Half-Pint: Glep's the smallest of the group (even smaller than Pim) but that doesn't stop him from being a feisty, back-sassing little fella.
  • Color Contrast: His design is almost entirely green and purple, and he makes a Red/Green Contrast with Alan.
  • A Day in the Limelight: Leads the B-plot in "Mr. Frog".
  • Face–Heel Turn: Joined the Frowning Friends simply because they have a better 401K plan. He leaves later.
  • Four-Temperament Ensemble: The Choleric; the most aggressive of the four employees, he's immediately willing to fight whoever opposes him.
  • Inconsistent Spelling: The official closed captions for the pilot misspell his name as "Fleb".
  • Incredibly Lame Fun: For some reason, the sight of him spitting is considered hysterical in the episode "Mr. Frog", to the point where it caused the staff behind the titular Show Within a Show to erupt in EXTREMELY violent laughter during a script reading. That said, the show consists of the exact same structure and script every episode and it rakes in millions of cheering viewers each time, to the point that the fans start booing once Rex changes the formula too much, so it clearly doesn't take much to get the show's audience howling.
  • Intelligible Unintelligible: Other characters seem to understand what he's saying despite his "speech" sounding like gibberish. Some time in the future, he gets the ability to speak actual English, though it could be just Translation Convention for the story he tells to his grandson.
  • The Napoleon: He has a few moments. He gets fairly argumentative with his gibberish, and he's not afraid to literally spit in the face of his job recruiter and potential boss for insulting him. He also eagerly took up the chance to punch Charlie in the knee when he (temporarily) quit the Smiling Friends.
  • Narrator All Along: He is revealed to be the narrator of the first season finale.
  • Not a Morning Person: Going by the opening of "Shrimp's Odyssey", Glep starts his mornings barely even able to open his eyes and needs a coffee cup bigger than himself to get started on his day.
  • Ridiculously Cute Critter: He's a cute little lizard-like character whose googly eyes make him look like a plushy brought to life that babbles like a baby.
  • Ridiculously Successful Future Self: It's shown through a Freeze-Frame Bonus in the first season finale that Glep will eventually become The President.
  • The Slacker: Spend the opening scene sleeping on his beanbag and later was seen watching a video on a tablet. Though he did later take up a mop after the Bliblies' invasion.
  • Screw This, I'm Outta Here: Immediately bolts and leaves his coworkers behind as soon as the TV screen shatters at the end of the pilot.
  • Spiteful Spit: He spits on the TV exec's face when he auditions for Mr. Frog, which somehow ends up landing him the role. However, despite his spitting being wildly popular with both his fellow cast members and with test audiences, the exec forbids him from spitting on the show, leading to Glep's debut performance being a tremendous flop.
  • Tiny Guy, Huge Girl: Word of God states the blonde human woman thrice his height he's been seen with is his wife, who is named Marge Simpson (no relation).
  • Vocal Dissonance: He's got a much deeper voice when he's yet to have his coffee.
  • What, Exactly, Is His Job?: It's unknown what his role in the Smiling Friends charity group is, as Allan seems to be in charge of maintaining the office and its supplies, doing things like washing the dishes and checking the fridge. Glep is seen mopping the floor at the end of "Desmond's Big Day Out", but he simply could have volunteered to do that in Allan's place, given that sort of task would fall under his jurisdiction, as well as Allan being injured by the Bliblies, meaning he could've required a break from his job so he could recover.
    • When pressured by a difficult client in the season 2 premiere, Charlie admits he has no idea what Glep's job is.

    The Boss 

The Boss/Mr. Boss

https://static.tvtropes.org/pmwiki/pub/images/2020_04_04_12.png
"Now get out there and make someone smile!"
Voiced by: Marc M.
An unpredictable billionaire and nurturing father who is the founder and head of the Smiling Friends office.
  • Accidental Hero: He spends most of the episode "Frowning Friends" suffering through a psychotic break, cumulating in him trying to murder Grim and Gnarly. This however ends up making the Frowning Friends fall out of favor with everyone when Grim cowers in fear when Mr. Boss holds him at gunpoint right after he said that nothing matters because everyone's going to die.
  • Ambiguously Human: While Pim, Charlie, Alan, and Glep are Critters, with the Boss it's a lot harder to tell. Presumably, he's the the Token Human just by relative comparison to his employees, but his oversized head, bizarre mannerisms, and the fact that he can breastfeed his son really make it hard to buy. On the other hand, when the puppet remake of "Shrimp's Odyssey" used puppets for "Critters" and other nonhuman characters, and live-action actors for human characters, Mr. Boss was depicted as the latter, albeit with a papier-mâché mask of his cartoon self.
  • Ambiguously Trained: The way he wields his iconic loaded M16 seems to imply that he's handled it before, when he snaps and goes to gun down Grim and Gnarly in the episode "Frowning Friends", as he runs holding it sideways against his chest, with the barrel pointing into the air, tackles a door open rather than stopping to open it with his hands and adjusting his aim so that Grim's still in his line of fire when the latter gets down on his knees and hands and begs for his life, but there's no other indication that he's served in the military, like a medal.
  • Ascended Extra: Only has two scenes in the pilot, one of them being mere seconds long. He then goes on to be the most prominent of the supporting characters in the first season.
  • Ax-Crazy: The Frowning Friends' relentless business success completely pushes him over the edge and turns him into a snarling, gun-toting maniac. This doesn't last long, thankfully.
  • Benevolent Boss: Kind and orderly with his subordinates, but can be a bit neglectful of his duties. The fact that Charlie can call him "crazy sometimes" and not get disciplined shows how relaxed his work environment is.
  • Beware the Nice Ones:
    • He participates in the brutal death of the Forest Demon in "A Silly Halloween Special" with the same equal amount of disturbing savagery that the rest of the partygoers do. He even eats the flesh from one of the arms of the fallen demon after he presumably tore it off.
    • He's so incensed by the Frowning Friends' rapid success and negative impact on his business that he actually charges into their compound and holds them both at gunpoint with an assault rifle.
  • Big Good: As the head of the Smiling Friends office, he is in charge of the rest of our protagonists.
  • Break the Cutie: He undergoes a shockingly realistic mental breakdown over the course of "Frowning Friends" due to the titular rival charity's success causing a majority of losses for the Smiling Friends goals and finances. This culminates in him becoming a furious, constantly snarling M16-wielding maniac out for the blood of Grim and Gnarly, until the sight of Grim breaking down and begging for his life makes him regain his composure, subverting it.
  • Bunny-Ears Lawyer: He's certainly a very eccentric man, but he also runs an incredibly successful charity that makes enough money to lose 2.4 billion dollars in a few days. He also responds to each client personally before sending Pim and Charlie on the job, and in "Frowning Friends" he's even the one who cheers up the episode's "client".
  • Casual Danger Dialogue: When he points his M16 at Grim and the latter breaks down begging for mercy, Mr. Boss regains his composure to say that he was just going to kill him in a rather casual tone. Somewhat justified as Grim had displayed nihilistic viewpoints up until now and, had he actually believed in what he said, wouldn't care too much about his own imminent demise.
  • Clark Kent Outfit: Downplayed. He has a lean, muscular Bruce Lee-esque build underneath his suit that you wouldn't be able to guess he has underneath his suit if it weren't for the scenes showing him with a bare chest.
  • Cloud Cuckoolander: Downplayed. He has some moments of eccentricity, such as randomly starting to speak in a southern accent and dressing bizarrely, but aside from this, he's relatively normal and down to earth.
  • Cool Old Guy: Considerate of Pim and Charlie's feelings, and isn't shy to show them his support. Also enjoys videos games despite looking like he's easily in his 60s or 70s.
  • Creator Thumbprint: The Boss' first scene has a strong resemblance to Zach's promo video for the Gremblo Art Show, down to him chastising his son for biting him.
    • The sudden drawl he adopts is fairly common in Marc M.'s work as well.
  • Creepy Good: He's undeniably off-putting and looks like he came right out of a MeatCanyon cartoon, but he still runs a company solely dedicated to making other people feel better and seems to take enthusiasm in this role.
  • The Cutie: He might be an older man, but he's a kindhearted and caring individual who comes across as being nice to virtually everybody and is generally an incredibly benevolent character who loves making the world a better place, even if it's one step at a time, to the point where he founded a charity based off of doing this.
  • A Day in the Limelight: For once he takes an active role in the story during "Frowning Friends".
  • Dark Is Not Evil: His office is a black expanse of a room that's hard to tell the actual size of but he's nothing but benevolent.
  • Dodgy Toupee: Possibly. The dark-colored hair on the top of his head appears to be a toupee that's several sizes too small for his head, but it's unknown if it is one or if it's his actual hair.
  • Elemental Motifs: A minor example, but he has some association with darkness, as his office is a vaguely shaped black expanse, he dresses in a dark suit, and some scenes with him tend to be associated with dimming lights or low light levels in one way or another, such as him talking to Pim at sunset in "A Silly Halloween Special" as an example.
  • Ensemble Dark Horse: Invoked by the Boss, who refers to himself as "your favorite character; The Boss".
  • Establishing Character Moment: His first appearance solidifies him as both equally creepy and offputting but also kind, supportive, and nurturing.
  • Fan Disservice: In "Charlie Dies and Doesn't Come Back", he is seen wearing nothing but an elf hat, vest, and speedo, exposing his gross wrinkled body for the audience to see.
  • Fiction 500: Parodied. In "Frowning Friends", he casually mentions that his company lost $2.4 billion since the Frowning Friends moved in across the street, which was only a few days prior. Keep in mind that the Smiling Friends seem to consist solely of a single small office building and less than a dozen employees.
  • Gross-Up Close-Up: Any time he's much closer to the camera than usual, he's animated with more veins and wrinkles than normal.
  • Good Parents: Zig-zagged. He seems to be very playful and certainly very nurturing to his infant son, but sets him aside on his desk instead of placing him in a crib.
  • Hidden Depths: He seems to be an avid gamer with him playing Real-Time Strategy games in the pilot and also playing a Dance Dance Revolution-esque game in "Frowning Friends" as well is any indication. He also sold his likeness to appear in a platform fighter, the same one Gwimbly and Troglore got into.
  • Nice Guy: Runs a noble cause and does so in a very polite and friendly manner. Part of the hilarity of his character is just how much his disturbing behavior contrasts with what a genuine Benevolent Boss he is.
  • Nipple and Dimed: The FCC guys mind if a guy eats without a mosaic censor.
  • No Name Given: Even he just calls himself The Boss. In his hallucinations he's called "Mr. M", but that's the most we get.
  • Not Worth Killing: Decides this about the Frowning Friends when he sees Grim begging for his life on his knees with piss streaking down his pants. He's quite satisfied with publicly destroying their reputations when their followers see what cowards they are. He even buries the hatchet with them immediately before they get killed by the Renaissance Men.
  • Office Golf: Plays Real-Time Strategy games with his guildmates during company hours. He's later seen playing Dance Dance Revolution as well.
  • O.O.C. Is Serious Business: The arrival of the Frowning Friends makes him incredibly unsettled, in contrast to his usually chill demeanor. He eventually goes fully Ax-Crazy and starts hunting them with an M16.
  • Sanity Slippage: Played for Drama. He has an agonizing emotional and mental breakdown over the course of "Frowning Friends", which starts with him simply being stressed and panicked, before he starts to hallucinate his struggles to deal with the episode's titular rival business as figures giving him useless advice, which gradually culminates in him hallucinating his reflection as a demonic, wrathful version of himself who insults him and urges him to do something that he vehemently disagrees with. It turns out that his mirror self's demands were to kill the Frowning Friends when he arms himself with an M16 to go hunt down the two so that he can gun them down in cold blood. Thankfully he regains his composure after seeing Grim beg for his life after he made a big speech about how nothing matters because everybody is going to die one day, exposing him as a hypocrite in front of a huge crowd that the Frowning Friends rallied.
  • Sharp-Dressed Man: The classic businessman attire of a black tux.
  • Token Human: He's the one and only human being (albeit a very strange human) in a core cast of critters.

    Smormu 

Smormu James Carter

https://static.tvtropes.org/pmwiki/pub/images/screenshot_2022_01_12_151026.png
"Dada dee dado, dada deedee dade do!"
Voiced by: Chris O'Neill
The fifth Smiling Friend voted into the show due to a nationwide online poll. At the end of his debut episode, the votes are counted and he is inducted as the fifth official Smiling Friends cast member. Then he dies.
  • Audience Participation: invoked Was introduced as part of one, where people would text their opinion on whether he would be in the show. The rules of the poll were comically lopsided in Smormu's favor.
  • Creator's Pet: Invoked. The poll over whether he should be added to the series was clearly designed to result in the pro-Smormu vote winning, between casting a vote for Smormu being significantly easier than casting a vote against Smormu, the poll having an Electoral College, and this Electoral College being overridden when Smormu loses it but (as a result of the easier text to vote for Smormu) gets more votes cast in his favor overall.
  • Dies Wide Open: His "in loving memory" photo is of him on a slab at the morgue, eyes and mouth wide open for reasons unknown.
  • Dropped a Bridge on Him: The after-credits gag memorial is of Smormu himself, dying in 2022. This death is permanent.
  • Early-Bird Cameo: Seen near the end of Episode 2 in a YouTube thumbnail.
  • Gory Discretion Shot: Downplayed, but going by the fact his eyes and mouth are stuck open, and his face is heavily bruised, whatever happened to him was probably pretty brutal.
  • Last Disrespects: Whoever was assigned to pick his funeral picture didn't even bother to grab one from life, they just snapped a photo of his gawking and bruised corpse on the morgue table and called it a day.
  • Mythology Gag: The little theme he sings at the end is Lyle's iconic channel intro as a snake charmer/Lets's Play-er.
    • The television poll he was part of - as well as him doing nothing but singing - resembles ringtone characters such as Wonki, which were also referenced on OneyPlays.
      Chris O'Neil: There's a version of that Smormu song with lyrics.
      Zach Hadel: Oh yeah, there is! It sounds like a little Jamster song.
  • Nothing Is Scarier: However he died, it clearly wasn't pretty, given that his eyes and mouth are wide open and his face is covered in bruises on his "in loving memory" photo of him.
  • The Scrappy: An In-Universe one. The vote for whether or not he should join the Smiling Friends is almost split right down the middle... because the text to vote against him is vastly longer and more complex than the text to vote for him. Charlie straight-up leaves once he finally shows up and starts dancing.
  • Shoo Out the New Guy: His ultimate fate. And barely a minute after his first appearance!
  • Sixth Ranger: To the main four employees.
  • Take That!: invoked To halfassed additions to a show's core cast, especially ones that get shilled to high heavens.
    Announcer: IT'S SMORMU! YOU VOTED, AND WE LISTENED! THIS CANNOT BE UNDONE! SMORMU IS HERE TO STAY!
    • His shirt also has the "I'm With Her" sticker slogan of the 2016 Hillary Clinton campaign, which fits with his voting results.
  • We Hardly Knew Ye: Only appears for the Gainax Ending, and is shown dead after the credits.

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