The Drew Carey Show : Drew's Reunion (1999)
Directed by Gerry Cohen
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Synopsis by Hal Erickson
With the gang's high school reunion approaching, Kate (Christa Miller) hopes to spend quality time with class geek-turned-computer billionaire Patrick Wells (Stan Cahill), while Lewis (Ryan Stiles) somehow manages to persuade Bo Derek to be his date. At the festivities, Drew (Drew Carey) is surprised that former cheerleader Kelly Walker (Anna Gunn), who used to cut him dead, is now fascinated by him and won't leave him alone. Meanwhile, Oswald (Diedrich Bader) is hilariously humiliated by his old classmate Stacey (Missi Pyle), once fat and ugly and now trim and beautiful--and thirsting for revenge! This episode is highlighted by a performance of the song "Whip It", to say nothing of Drew's shocking confession at the end (shocking, that is, to everyone but the viewers).