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The Main Group
Drew Allison Carey (Drew Carey)
''I always get screwed by the system. That's my place in the universe. I'm the system's bitch."The title character is the Assistant Director of Personnel at Winifred-Louder, a department store. Much like Dilbert (and just to hammer the point home, Drew is a Dilbert fan) he must constantly contend with nutty bosses, strange friends, and unsuccesful romances.
- Big Eater: Uh-huh. You can count the episodes that don't mention his eating habits on one hand. It's mentioned that he orders so much pizza that he's gotten multiple delivery boys through college!
- The Chew Toy: Where to begin? He's overworked and unappreciated at a dead end job. His parents openly prefer his brother to him. Two women he dated ended up getting married mere months after breaking up with him. He's even resorted to marrying his boss, Mr. Wick, in order to get his job back in season six.
- Embarrassing Middle Name: Drew Allison Carey.
- Extreme Doormat: He has trouble standing up for himself. Even as an adult he still gets pushed around by his older brother and can only respond with a wimpy slap to Steve's bald head.
- "Friends" Rent Control: Inverted. Despite having a decent white-collar job, his living conditions aren't that great.
- Heroes Love Dogs: Very devoted to his dog, Speedy.
- Nerd Glasses: A large part of his signature look.
- Nice Guy: Works hard and is one of the most honest employees at Winfred Louder. Sadly, this doesn't stop the universe from piling crap on him.
- Sitcom Arch Nemsis: Mimi is this to him. She inexplicably took his comments during her job interview as sexist, and it spiraled from there when she got hired.
- Ugly Guy, Hot Wife: More average looking than ugly but many of the women Drew dated over the course of the series have been absolute knockouts, with several of them including Christa Miller, Kate Walsh, Jenny Mc Carthy and Cynthia Watros.
- The Unfavourite: Not as extreme as some other sitcom examples but still noticeable in flashbacks. Drew's brother was the more outgoing, popular and athletic sibling when they were growing up. He remains this ever after revealing himself as a crossdresser in the third season.
Kate O'Brien (Christa Miller)
- One of the Guys: She's this to Drew, Oswald and Lewis.
- Put on a Bus: Gets married at the start of Season 8, moves away, and is never heard from again.
- Really Gets Around: Her promiscuity is often played for laughs. This trait even earned her a nickname in high school, "Give It Away Kate".
Lewis Kiniski (Ryan Stiles)Lewis is one of Drew's friends. Your basic know-it-all and troublemaker, he's a janitor at a shady company called Drug Co.
- The Blind Leading the Blind: He's smarter than Oswald, but his advice to the guy tends to suck.
- Cloud Cuckoo Lander: He and Oswald both do weird stuff and are really immature.
- Conditioned to Accept Horror: Drug Co has insane experiments going on all the time. Cloning, giant insects, realistic holograms...Lewis is fairly blasé about it all and casually tells his friends about his job all the time.
- Those Two Guys: With Oswald. They do everything together, and it often has little to do with the plot.
- Insufferable Genius: In one of the later seasons it's revealed by his mother he has an IQ high enough to join MENSA. Predictably, this inflates his ego to insane levels. He was also straight A student before he met Oswald.
Oswald Harvey (Diedrich Bader)
- Flanderization: He starts out as the dimmest member of the group, but in a Book Dumb sort of way. He gets progressively dumber as the seasons go by.
- Heterosexual Life-Partners: With Lewis. In a Season 3 episode his bride to be forced him to go to pre-marriage counseling when she realized he listened to Lewis more than her.
- Punny Name: His name is clearly a play on Lee Harvey Oswald.
Kellie Newmark (Cynthia Watros)
- Fragile Flower: Why Oswald and Lewis initially didn't care for her replacing Kate. Due to the problems in her life up to that point, Kellie couldn't take the usual insults. She gets better, though.
- Will They or Won't They?: Has this back-and-forth with Drew for much of Season 8. Gets thrown a sudden curve ball in Season 9 when their one-night stand leads to her being pregnant.
Mimi Bobeck Carey(Kathy Kinney)
- Excessive Evil Eyeshadow: The unpleasant Mimi just loves her makeup. Drew calls her a clown every chance he gets.
- Friend to All Children: Yeah, seriously. Mimi isn't good with kids (most parents would think she's irresponsible), but she has a soft spot for them and they adore her wild antics.
- Hypocritical Humor: Constantly insults Drew's weight despite being much fatter than him. For some reason, Drew never responds in kind.
- Jerk Ass:
- Sitcom Arch-Nemesis: To Drew, though it tones down a bit in the last few seasons.
- The Thing That Would Not Leave: In Season 9, Gus burns down her house, which forces them to move in with Drew. While Drew tolerates it for his nephew's sake, there are times he really wants to get Mimi out of his house.
- Unlimited Wardrobe: Of really, really loud, gimmicky outfits. Holiday episodes milk this for all it's worth.
Steve Carey(John Carroll Lynch)
- The Bus Came Back: Season 9's "Love, Sri Lankan Style"
- Out of Focus: Appears less often in Season 8.
- Wholesome Crossdresser: Revealed to be this in his debut episode. Drew, understandably, is not happy with it at first but ends up supporting his brother and fighting for him to keep his job at the Winfred Louder cosmetics counter.
- Your Cheating Heart: A Season 8 arc is devoted to him cheating on Mimi and having to win her back. When Lynch left the show for good before Season 9, though, Steve cheated on Mimi again, and they divorced.
Nigel Algernon Wick (Craig Ferguson)
- Bad Boss: What he was flanderized into. Besides becoming more cartoonish in general, he'd abuse and fire subordinates just for the hell of it and often didn't seem to have the slightest idea how to do his job.
- The Bus Came Back: Disappears early into Season 8, but he returns for the season finale for Drew's wedding. He reappears again in the last two episodes of Season 9, which means it doubles as Back for the Finale.
- Mama's Boy: And damn proud of it, too!
- Mean Boss: What he started out as. He was certainly competent and qualified, but he was also a scheming manipulator and openly callous to subordinates.
Larry Almada (Ian Gomez)
- The Bus Came Back: Stops appearing after "Brotherhood of Man" due to Gomez being cast as a regular on The Norm Show. He returns in "Chemistry Schmemistry" when Drew bumps into him and learns he became a matchmaker.
- Jerk with a Heart of Gold: He starts out as an obnoxious, at times even criminal co-worker who helps Drew out now and then.
- Took a Level in Kindness: When he returns in Season 8.