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The Main Group
Drew Allison Carey (Creator/Drew Carey)
''I always get screwed by the system. That's my place in the universe. I'm the system's bitch."
- 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.
- Nerd Glasses: A large part of his signature look.
- Nice Guy: Works hard an 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.
- 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)
- 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)
- Heterosexual Life-Partners: With Oswald.
- 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)
- 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)
Mimi Bobeck Carey(Kathy Kinney)
Steve Carey(John Carroll Lynch)
- 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.