--> ''When I started S*P, all the characters were meant to represent a friend everyone had. Davan's the hard-to-like friend who, while trying, WILL be there for you. Aubrey's the friend who tests your limits. [=PeeJee=] is the friend who acts tougher than she probably is and cares a little too much. Scotty's the friend you lose and you never understand why.''
--> Randy Milholland

!!Davan [=MacIntire=]

-->The main character and AuthorAvatar, representing Milholland when he was a younger man. Davan is snide, sarcastic and takes most of life with an uncaring, unsympathetic nature, which often gets him into trouble. Still, he cares deeply for his friends and family, despite his cynical nature.
--> Randy's own words on the subject: "Near the end of the first year. I realized quickly I didn't want this comic to be autobiography. Even when it started, Davan wasn't who I was then - he was who I'd been a few years before and, I should add, someone I didn't like (I find it funny when detractors claim Davan is who I think people should be and is "cool" - it proves they've never spoken to me or done a bit of research. Davan's an asshole and a lot of the misery he's gone through, he brought on himself)."

* AffectionateNickname: "Monkey Butter", for Aubrey.
* AuthorAvatar: From a time in Randy's life when he was especially cynical and dreary.
* BerserkButton: Never sass Mister Peppermint around Davan.
* BetterAsFriends: Decided this about himself and [=PeeJee=] and reveals it to her long after the fact.
* ComedicSociopathy: He makes fun of all his closest friends. Notably, when Mike is surprised that Davan is acting friendly instead of "making fun of me like you usually do", Davan points out that if he and the others ''wouldn't'' make fun of him if they didn't like him.
* DeadpanSnarker: His chronic, over-arching trait, and one that bothered many people, including then-girlfriends Eva and Celie.
* TheEeyore: [[DeconstructedTrope Deconstructed.]] The constant negativity he gives off has had a ''very'' bad affect on his life, often in his relationships with women. It's also shown that he doesn't handle positive behavior from others well, either annoying him or leaving him confused.
* FatalFlaw: His negativity. Davan embraces the inherent cynicism of the world he lives a little ''too'' much for even his own friends, notorious cynics in their own right, to be comfortable with and he can barely function when met with genuine positivity.
** This is actually the biggest problem he has in his relationships with other women as the ones that are willing to give him a chance are ultimately driven off by his pessimistic behavior. The only working relationships he has had have been with women that are a bit off in their own ways.
* FreudianExcuse: [[PlayingWithATrope Played with.]] The large amount of misfortune that has happened to his family definitely feeds into Davan's cynical outlook on life, but isn't clearly defined as the cause of it.
* GenreSavvy: While others are worried about Ollie once he comes into a substantial inheritance, since he has a ''very'' large enmity towards Davan, Davan isn't as he has witnessed how incompetent Ollie actually is.
* HappilyMarried: [[spoiler: With Vanessa.]]
* [[HardDrinkingPartyGirl Hard Drinking Party Guy]]: Back in the early days of the strip, he was much worse. He has stated that his combined German, Irish and Native America heritage makes it literally impossible for him to allow alcohol to be wasted.
* IgnoredEnemy: Ollie Pompey, the badly abused nephew of the late (and horrifyingly nasty) theatre director Avogadro Pompey, really, ''really'' hates Davan, to the point of wanting to destroy him. Davan hadn't realized this, and mostly found it pathetic when he found out.
* InformedDeformity: Women in the strip used to react as if he was the ugliest human being alive, despite him being drawn in a rather ordinary fashion. This plays into his status as the AuthorAvatar--Randy himself doesn't like his appearance.
* IWantMyBelovedToBeHappy: When perfect-girlfriend Branwen gets a dream job offer, Davan tells her to take it.
* {{Jerkass}}: Randy specifically calls him out on a lot of it. Eventually evolves into a JerkWithAHeartOfGold.
* KavorkaMan: For an ugly dude, Davan has slept with upwards of six or seven hot women since the strip began in 2001.
* LawOfInversePaternity: Played with; Davan didn't want to be Rory's father, but was at least willing to step up if he was, unlike the other candidate. Davan wound up becoming his ParentalSubstitute even after finding out he wasn't the dad, and admits that in retrospect he wishes he had been the father after all.
* LikeBrotherAndSister: With Aubrey.
* LimitedWardrobe: He can wear various things, but he generally wears work shirts from his father's old job in a helicopter factory.
* LookingForLoveInAllTheWrongPlaces: A recurring trend is for Davan to meet up with women who inevitably turn out insane. At least Branwen and Vanessa are ''comedically'' nuts.
%% * NoGoodDeedGoesUnpunished
* ParentalSubstitute: To Rory, to the point where Rory actually considers Davan his dad.
* PlatonicLifePartners: With [=PeeJee=].
* StrongFamilyResemblance: Davan clearly takes after his dad.
* TheyDo: [[spoiler:With Vanessa, at the end of 2013.]]
* {{Troll}}: Especially when working together with Jason.
* VitriolicBestBuds: Pretty much the nature of the comic. They all prank and tease each other mercilessly.
* WriteWhatYouKnow: Davan used to work for [=MedicAid=], doing the same work Randy did before his webcomic really took off- billing poor people for ambulance fees.

!!Penelope Jennifer "[=PeeJee=]" Shou

--> A Canadian girl who moved down to Boston to meet up with some online friends, [=PeeJee=] is a devoted pal to the others. She's much like Aubrey, but far more emotional and liable to feel sympathy, or the need to cry. Randy has stated that she represents "those friends who aren't quite as tough as they seem". One of her key early traits was a huge crush on gay cast member Jhim. Despite the vitriolic nature of most of the characters, they openly felt sorry for her.

* CollectorOfTheStrange: Her new hobby is looking for the most fucked up sites possible, having filled up four external hard drives worth of 'em.
-->Vanessa: I have seen suicidal notes less depressing than this.
-->[=PeeJee=]: Oh, really? Are there any suicide notes that mention cool sites involving Russian amputee mail order brides?
-->Vanessa: I dunno. Are there?
-->[=PeeJee=]: ...Yes. Sixty-three. They're on hard drive two.
%%* GenreSavvy
* KaleidoscopeHair: For a long time, [=PeeJee=] would have constantly changing hair, until Randy got tired of changing it.
%%* KnightInSourArmor
* TheNotLoveInterest: To Davan, something he decided long after the fact, and to Mike, on the grounds that it was a one-sided infatuation and Mike had blown any chance at something deeper.
* PlatonicLifePartners: With Davan, and...
* VitriolicBestBuds: With Aubrey. Everyone else is [[ComedicSociopathy fair game]], though largely in the earlier days.
* WhyDidItHaveToBeSnakes: [=PeeJee=] has a fear of puppets, and breaks Aubrey's hand with a hammer when Aubrey sneaks up behind her with a handpuppet.
* YaoiFangirl: Obsessed with gay men to the point of it being a large running gag.
* YouGottaHaveBlueHair: Or purple, or pink, or...

!!Aubrey Chorde

--> Davan's best friend from childhood, and completely platonic. She's the devious schemer of the group, and rarely gets overly-sympathetic or mushy. She's based off of Randy's own best friend from childhood, anime voice actress Clarine Harp.

* AffectionateNickname: "Woogie", for Davan.
* DoubleStandardAbuseFemaleOnMale: She & [=PeeJee=] got away with this ''a lot'' in the early days, often as the [[ComedicSociopathy punchline]] to a comic strip.
* HappilyMarried: To Jason.
* {{Jerkass}}: One of the most malicious cast members.
* LikeBrotherAndSister: With Davan, whom she grew up with.
* MamaBear: Brutally crushes the hand of a MonsterClown who attempts to threaten [=Pamjee=].
--> '''Aubrey:''' Touch my child again and you will learn that eating solid food is a privilege I can and ''WILL'' revoke.
* NightmareFetishist: Do not share disturbing ideas with Aubrey, unless you are actively looking to provide her with potential business endeavors.
* ReasonableAuthorityFigure: Curiously enough, she runs a tight ship over at Nerdrotica, her combination tech support/phone sex company. Her early sadistic antics do not translate over to her employees, who at worst suffer harmless pranks or demeaning (but necessary) job details.
* RelationshipUpgrade: Eventually marries (and adopts a child with) Jason.
* VitriolicBestBuds: Possibly the nastiest of the whole crew.
* WriteWhoYouKnow: Anime voiceover actress Clarine Harp, herself one of Randy's friends from childhood in Texas.

!!Jason Chorde (né Pratchett)
--> A jovial fat guy who was an early acting friend of the gang, and stuck around in all later arcs. Probably the smartest of the gang, and most manipulative. He's the most committed to his schemes (such as the catgirl webcomic).

* BiggusDickus: Women have recoiled in fear of it.
* BigScrewedUpFamily: Setting aside his horrible relationship with his father, Jason also has circus workers (clowns, specifically) in his family tree. When his daugher [=PamGee=] discovered this, [[TroublingUnchildlikeBehavior she was positively]] ''[[TroublingUnchildlikeBehavior giddy]]''.
* GirlOnGirlIsHot: At one point Aubrey and [=PeeJee=] tease him with the possibility of a threesome, though only to mess with him.
* HappilyMarried: To Aubrey.
* KavorkaMan: Despite his obesity, he has a mathematical program designed for easy short-term dating success (ie. hook-ups).
* TheMaidenNameDebate: He changed his name when he married Aubrey because of his hatred of his father.
* RelationshipUpgrade: Eventually marries (and adopts a child with) Aubrey.
* {{Troll}}: Especially when working together with Davan.
** And given his delight at being given their own parking space for parent-teacher conferences, this appears to be his approach to parenting.
* WriteWhoYouKnow: Jason is based off of one of Randy's friends from his acting days in Boston, who still runs part of his website.

!!Kharisma Valetti
--> An early recurring antagonist, Kharisma was a high-and-mighty actress with a love for money, and a hatred for the ugly little people (like Davan). After doing many horrible things to many people, she met with a few PetTheDog moments by giving Davan some much needed advice about quitting his job. Then she got into a murder pact with Avagodro Pompey, got arrested, got broken out of jail, and now she's on the run with a possibly-real psychic manifestation of annoyance called Fluffmodeus.

* ActionSurvivor: Extremely bad, typically illegal, and occasionally lethal things end up happening around Kharisma, with or without her knowledge. A large part of her CharacterDevelopment is evolving from a [[AlphaBitch repulsive]], flighty, [[GoldDigger gold-digging]] brat into a scarred, street-tough, half-mad ex-con.
* AssholeVictim: Horrible things happening to a horrible person.
* TheBrainlessBeauty: Pre-CharacterDevelopment, Kharisma was by her own admission "a cheerleader in high school who specialized in seducing nerds", a mindset that carried into her adult life.
* CharacterDevelopment: Went from a stupid RichBitch to a more sympathetic (but possibly insane) fugitive, and has settled into a life doing sketchy odd jobs under the name Nancy in a vague rural location.
* TheChewToy: Said sketchy odd jobs include freelance collections agent/legbreaker and babysitter for stupid druggies. This is after getting framed for a murder she was going to commit anyway but didn't have a chance to, scorching her own face with an AerosolFlamethrower, spending time in jail, and finding out that the benefactor that helped her out of prison was an anti-stuffed-animal-cruelty vigilante.
* ImaginaryFriend: Fluffmodeus, aka "The Little Blue Thing". Whether it is just a manifestation of Kharisma's fear and woefully underdeveloped survival instincts, or a separate and ill-meaning entity who only shows itself to Kharisma has been a matter left deliberately ambiguous.
* InsistentTerminology: No, Kharisma, the police aren't going to lift the murder charges just because at the time Avogadro died you were merely ''"trying"'' to kill him "with his blessing". Enjoy prison.
** Fluffmodeus meanwhile has a somewhat sinister habit of always calling Kharisma "''New'' Friend".
* LaserGuidedKarma: ''Look up''. Nearly every bad thing that has happened to Kharisma has been a direct result of her own poor judgement, before prison anyway.
* PetTheDog: A rare few times: Notably, she gave Aubrey the idea for Nerdrotica, her combination tech support/phone sex company, and beseeched Davan to quit his horribly medical billing job, telling him "I wouldn't wish it on the worst person in the world. Or you, either."
* RichBitch: Though only due to aggressive [[GoldDigger gold-digging]]. Prior to her stint in prison, Kharisma's only marketable skill was identifying the most successful (and receptive) man in the room and bedding him.
* SleepingWithTheBoss: Kharisma makes no secret that she'll sleep with anyone for advancement (and is later fired without ceremony when the boss' fetish goes from redheads to blondes).
* TookALevelInBadass: Kharisma's skill at seduction and gold-digging didn't translate very well to life in prison, forcing her to drop the spoiled brat routine and [[HADToBeSharp sharpen up lest she get killed]]. Now that she's on the run and doing various extra-legal things to provide for herself (including leg-breaking and drug-running), "Nancy" is almost a [[DiscardAndDraw completely different character]].
* WriteWhoYouKnow: Early Kharisma material was derived from a woman who was friends with Randy until she saw a picture of him and declared him not attractive enough to stay her friend.

!!Monette [=MacIntire=] (formerly Donnelly)

--> Initially a recurring annoyance, the idiotic Monette would foolishly attempt to become a lesbian, despite her sucking "a whole mess of dick", according to Davan. Eventually, she randomly moved to Texas to hang out with Davan's parents, and ended up getting ''adopted'' by them, becoming a family member. She eventually realized she was bisexual and hooked up with her girlfriend Lisa, and moved to West Hollywood to appear in a bad UPN sitcom.

%%* BiTheWay: Sorry, fellow tropers, but I just don't know how not to make this a zero-context example
* CharacterDevelopment: From comedic ButtMonkey slut character to a worthy cast member with her own foibles and rare instances of insight.
* DeadpanSnarker: Develops shades of this as time goes on, possibly from exposure to Davan's parents. In fact, one of her first reveals of this side causes Dahlia to respond "Welcome to the family."
* TheDitz: Especially at first.
* HilariouslyAbusiveChildhood: While the consequences of her terribly neglectful father have been played a bit more seriously, the exaggerated level of this neglect has been used for BlackComedy.
* ObfuscatingStupidity: PlayedForLaughs.
* SincerestFormOfFlattery: When Monette gets the chance to write for her TV show, she [[{{WriteWhoYouKnow}} creates a character that is a clear Expy of Davan]]- to the point of using some lines that Davan's previously said.
* WhatHappenedToTheMouse: Infamously miscarried off-panel, leaving fans going nutty.

!!Mike Dowden
--> An antagonistic, whiny nerd, Mike was and whiny, always insisted on being right, and made "friends" with girls in hopes of seducing them. Basically, he was Randy's version of a lot of needy, misogynistic geeks who chase after women. Eventually he made real efforts to change, found a girl, had a baby... and then broke down again, chasing some friends off. Usually, if the plot requires some regular character to [[StrawCharacter be wrong]], it'll be Mike. He's still sometimes sympathetic, but he's usually the universe's ButtMonkey.

* ButtMonkey: The strip's biggest recurring example. He gets a ''lot'' of beatings.
* CharacterDevelopment: Has gotten much better over the years, to the point where he could currently be considered one of the ''nicest'' characters in the strip. Is now a legitimate superhero (of the "real superheroes" variety).
** In a realistic inversion/back to straight playing of this trope, Mike briefly regressed to his original jerkish persona (due to being under a great deal of stress) before recovering and getting back on track.
* TheChewToy: ...Let's say his first day as Pythagorean was ''not'' kind to him.
* CosmicPlaything: A couple of strips have shown God actively plotting to fuck with him.
* TheFriendNobodyLikes: How he's introduced; it's not clear at first why anyone would hang out with a {{Jerkass}} like him, though he eventually grows out of it.
* HeroWithBadPublicity: [[AvertedTrope Averted]]. Turns out there's a whole bunch of folks in town doing the "dress in a superhero costume and do community service" gig, but Pythagorean is one of the first to gain ''positive'' recognition as something other than "some geek in a cape"...
** HumbleHero: ...Which makes Pythagorean something of a minor celebrity, a fact Mike was completely unaware of until a group of other "capes" help him escape a shady blogger bent on publicly unmasking him.
* JerkassHasAPoint: One of the major signs of Mike's improvement involved this - [=PeeJee=] was becoming increasingly angry at work because her boss' new girlfriend was blatantly and unapologetically racist (particularly towards Asians like [=PeeJee=]). Aubrey called a meeting to reveal a plan to mollify [=PeeJee=], and Mike objected due to it not solving the underlying problem. For one, it showed Mike showing genuine concern for another person with no angle towards himself. For another, it showed that everyone else agreed with him, only disagreeing as the distraction was useful as a stopgap measure - they were treating him as an equal and friend.
* MistakenForGay: His Pythagorean costume is an all-purple affair with a large rainbow triangle on the forehead. Mike insists it's a mathematical reference, but his friends are understandably concerned other people might not get it, with his wife likening it to a giant "I cordially invite you to fuck with me" sign.
* {{Munchkin}}: A bad habit that makes playing with him almost untenable; If he can't play his ridiculously overpowered amalgamation of stats, feats, and equipment that almost resembles a character if you squint a bit, he'll pout and complain the whole time.
* NiceGuy[=/=]NiceGuysFinishLast: Subverted heavily a major point of Milholland's (and Davan's) is that a lot of supposed "Nice Guys" are actually self-involved, self-pitying jerks like Mike, who are actually quite selfish, and only after most girls because of their looks (something they hypocritically accuse the girls of doing with the "jerks" they go out with). And that said "Nice Guys" often pretend to be girls' friends just to potentially seduce them later, while pining over them like stalkers, none of which is "nice" behavior at all.
** However, after his CharacterDevelopment he now has a girlfriend, a baby, and the respect of his friends (well, as close to respect as Davan, Aubrey, ''et al'' can actually express) for his superhero career.
* NonPoweredCostumedHero: One day he decided he wanted to affect a positive change on his community, specifically by becoming a superhero. His daily heroics as Pythagorean include helping people with their groceries, finding lost pets and generally just being a nice guy and he is well loved by the community at large for it.
* ObliviousToLove: His total lack of self esteem and inexperience with any kind of flirting, despite being ''married'' makes him unable to tell the multiple women (and at least one man) giving him their phone numbers were flirting with him.
%%* StrawLoser
* TookALevelInBadass: The eventual result of his superhero career, much to everyone's astonishment (particularly his own).
* WriteWhoYouKnow: Mike is an amalgamation of two people Randy knew -- both misogynistic whiny geeks. One person got better from that phase, while another got worse. Luckily for Mike, he seems to be following the example of the one who got better.

!!Jhim Midgett

--> Ironically, Jhim, the only recurring gay male character, is the Straight Man of the group, often rejecting the bizarre habits and statements of the others. He tended to get dragged into whatever crazy thing the rest of the gang was doing. He left Boston after a couple years of the strip after several failed relationships (one to a heavily-closeted man with a wife and son), and only returned when Davan left, making him a ''very'' rarely-recurring character. He's proven to be a bit of an EnsembleDarkhorse, being one of the most-requested characters for the "Old Familiar Faces" arcs.

* OutOfFocus: He used to be one of the main cast, and now more than a year often goes by between appearances.
* ShipperOnDeck: For Davan/[=PeeJee=].
* StraightGay: Despite joining a dance troupe and being into theatre.
%%* StraightMan
* WriteWhoYouKnow: Based off of a real-life person of the same name, and a friend of Randy's.

!!Fred [=MacIntire=]
--> Davan's cranky, sarcastic father. It's fairly clear which parent Davan takes after.

* CoolOldGuy
* DisabilityAsAnExcuseForJerkassery:
** As a young boy, he was admitted to a hospital for an ear infection, where he was antagonized at every turn by a boy in a wheelchair. Eventually, Fred and his friends team up to scare him and teach him a lesson... [[spoiler: whereupon it is revealed that the boy is in the hospital for a heart condition, and the shock of the scare ends up killing him.]]
** Not that he feels the need to make excuses, but Fred ''relishes'' being diagnosed with Alzheimer's because of the opportunities it allows him to fuck with people.
* GrumpyOldMan: Must be where Davan gets it, 'cuz the boy ''damn'' sure didn't get it from Faye.
%%* KnightInSourArmor
* ScrewPolitenessImASenior: Quite a few examples, but this one stands out; His response to a "Hell House"[[note]]a fundamentalist soapboxing masquerading as a haunted house [[/note]] telling him he has to "choose Jesus" if he wants to leave is to sit down in the middle of the floor.
* SecondLove: Faye was his. We don't know much about his first wife.

!!Dahlia [=MacIntire=]

-->Davan's older sister. She was partially paralyzed in a car accident about 10 years before the start of the series (she uses either a walker or a wheelchair, depending on the situation).

* ActionGirl: She was very athletic before the crash.
* BerserkButton: Being treated as InspirationallyDisadvantaged.
%%* DeadpanSnarker / DisabledSnarker
* DisabilityAsAnExcuseForJerkassery: This is her on a bad day. It's only exacerbated by the people who think that [[DisabledMeansHelpless "disabled" = "incapable"]].
* {{Meganekko}}
* StrongFamilyResemblance: Looks pretty much like a female Davan.
* SuperWheelchair: She attaches a cowcatcher for shopping during the Christmas rush.

!!Vanessa Cubbins
--> Davan's girlfriend upon his move back to Texas. She's a quirky, short bisexual girl who is a lot more innocent than the usual S*P character, making her quite unique to this world.

* BiTheWay: She's a bigger fan of strip clubs than Davan, no less.
* BunnyEarsLawyer: Once she got a taste of that kaiju power, there was no going back; there'll be days where she just walks around in a kaiju outfit like someone wearing a t-shirt and jeans.
* {{CloudCuckoolander}}: Her mind goes to weird places sometimes, which she is self-conscious of: She ends her first date with Davan by telling him she's going to go inside to "unleash all the clumsy and crazy I've been holding in all evening", and after prefacing it by making sure she won't "scare [him] away with [her] crazy", she likens her love for Davan to a small lizard that has found the perfect sunning rock; He makes her "lizard-happy".
* CovertPervert: She's bisexual, and just as dirty-minded as everyone else; This tends to be easily forgotten due to just how damn cute she is.
* TheCutie: Endearingly awkward, petite, nerdy, and cute as a button; Occasionally dresses up as a giant monster... Which is to say she's exactly the same size, but now wearing an adorable monster costume.
* FlirtyStepsiblings: Inverted; her first heterosexual romance was with an acquaintance who would later become her stepbrother. Awkwardness ensued.
* HappilyMarried: [[spoiler: With Davan.]]
* TheyDo: [[spoiler:At the end of 2013, wearing matching kaiju costumes, no less.]]

!!Mr. Sanderson
--> Davan's Boss. He's rich, snide, an enthusiast of drugs and alcohol, and generally a decent fellow.
* TheAlcoholic: His primary hobby besides "produce plays of dubious quality" seems to be "drinking expensive alcohol".
* BenevolentBoss: Treats Davan more like a colleague than an employee and goes out of his way to ''try'' and help Davan have some fun in his life. Davan actually dislikes this, partly due to not handling positivity in any form well and partly because Sanderson's good intentions have a way of backfiring on Davan.
* EccentricMillionaire: Rarely if ever are profits or losses mentioned in conjunction with the plays he produces, and yet his fortune endures, so either the plays are successful or he's got money to burn.
%%* DeadpanSnarker
* HappilyMarried: To his wife, in an [[{{Polyamory}} open marriage]] that seems to also involve prostitutes who sometimes break his heart by having affairs with his wife's boyfriends.
* ReasonableAuthorityFigure: He's willing to listen to Davan's advice and shows him a fair deal of respect and leeway; A far cry from [[BadBoss Davan's boss at his Medicaid job]].
* UnclePennybags: Very wealthy, and very generous with that wealth.