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The main character and Author Avatar, 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)."
- Author Avatar: From a time in Randy's life when he was especially cynical and dreary.
- Bottle Fairy: 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.
- Comedic Sociopathy: He makes fun of all his closest friends.
- Deadpan Snarker: His chronic, over-arching trait, and one that bothered many people, including then-girlfriends Eva and Celie.
- Informed Deformity: 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 Author Avatar- Randy himself doesn't like his appearance.
- I Want My Beloved to Be Happy: 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.
- Kavorka Man: For an ugly dude, Davan has slept with upwards of six or seven hot women since the strip began ten years ago.
- Law of Inverse Paternity: 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 Parental Substitute even after finding out he wasn't the dad, and admits that in retrospect he wishes he had been the father after all.
- Like Brother and Sister: With Aubrey.
- Limited Wardrobe: He can wear various things, but he generally wears work shirts from his father's old job in a helicopter factory.
- Looking for Love In All the Wrong Places: A recurring trend is for Davan to meet up with women who inevitably turn out insane. At least Branwen and Vanessa are comedically nuts.
- No Good Deed Goes Unpunished
- Platonic Life Partners: With PeeJee.
- Vitriolic Best Buds: Pretty much the nature of the comic. They all prank and tease each other mercilessly.
- Write What You Know: 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.
- Collector of the Strange: Her new hobby is looking for the most fucked up sites possible, having filled up four external hard drives worth of 'em.
- Knight in Sour Armor
- Platonic Life Partners: With Davan.
- Vitriolic Best Buds: With everyone.
- Yaoi Fangirl: Obsessed with gay men to the point of it being a large running gag.
- You Gotta Have Blue Hair: Or purple, or pink, or...
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.
- Abuse Is Okay When Its Female On Male: She & PeeJee got away with this a lot.
- Jerkass: One of the most malicious cast members.
- Like Brother and Sister: With Davan.
- Relationship Upgrade: With Jason.
- Vitriolic Best Buds: Possibly the nastiest of the whole crew.
- Write Who You Know: Anime voiceover actress Clarine Harp, herself one of Randy's friends from childhood in Texas.
Jason Chorde (nee 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).
- Biggus Dickus: Women have retracted in fear from it.
- Kavorka Man: Despite his obesity, he has a mathematical program designed for easy short-term dating success (ie. hook-ups).
- Relationship Upgrade: With Aubrey.
- Write Who You Know: Jason is based off of one of Randy's friends from his acting days in Boston, who still runs part of his website.
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 Pet the Dog 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 physic manifestation of annoyance called Fluffmodeus.
- Action Survivor
- Asshole Victim: Horrible things happening to a horrible person.
- Character Development: Went from a Rich Bitch to a more sympathetic (but still stupid) survivalist.
- Laser-Guided Karma
- Pet the Dog: She did this a few times, mainly to Davan.
- Rich Bitch
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 became a real lesbian after hooking up with girlfriend Lisa, and moved to West Hollywood to appear in a bad UPN sitcom.
- Bi the Way
- Character Development: From comedic Butt Monkey slut character to a worthy cast member with her own foibles and rare instances of insight.
- What Happened to the Mouse??: Infamously miscarried off-panel, leaving fans going nutty.
An antagonistic, whiny nerd, Mike was obsessive 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 be wrong, it'll be Mike. He's still sometimes sympathetic, but he's usually the universe's Butt Monkey.
- Butt Monkey: The strip's biggest recurring example. He gets a lot of beatings.
- Character Development: Has gotten much better over the years.
- Nice Guy and Nice Guys Finish Last: 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.
- Straw Loser
- Write Who You Know: Mike is an amalgamation of two people Randy knew -- both misogynistic whiny geeks. One person got better from that phase, while another got worse.
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 Ensemble Darkhorse, being one of the most-requested characters for the "Old Familiar Faces" arcs.
- Out of Focus: He used to be one of the main cast, and now more than a year often goes by between appearances.
- Shipper on Deck: For Davan/PeeJee.
- Straight Gay: Despite joining a dance troupe and being into theatre.
- Straight Man
- Write Who You Know: Based off of a real-life person of the same name, and a friend of Randy's.
Davan's cranky, sarcastic father. It's fairly clear which parent Davan takes after.
- Cool Old Guy
- Disability as an Excuse For Jerkassery: 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 wheel-chair. Eventually, Fred and his friends team up to scare him and teach him a lesson... 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.
- Grumpy Old Man
- Knight in Sour Armor
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.