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Scott William Winters

Actor Scott William Winters made his debut in 1996 in "The People vs. Larry Flynt"; he was billed as "Blow Dried Jerk," a harbinger of roles to come. Indeed, Winters played another sleazeball character in 1997's "Good Will Hunting." In a memorable barroom scene, Winter's smarmy Ivy Leaguer unwisely matches wits with Matt Damon's genius janitor. The result is that he loses the girl (Minnie Driver) and Damon's character taunts him with the bon mot, "How do you like them apples?" In 1997, Winters made two appearances as a police informant on the critically acclaimed detective drama "Homicide: Life on the Street." Interestingly, Winters's actor brother Dean (a.k.a. boyfriend-from-hell Dennis Duffy on "30 Rock") had also appeared on the show. In 1998, the pair were reunited in prison when Winters landed his best-known role on "Oz," as mentally impaired inmate Cyril O'Reily, brother to longtime prisoner Ryan O'Reily (Dean Winters). In later years, Winters continued to perform in crime dramas, among them "NYPD Blue," "Dexter," and "Law & Order."