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Gary Rosen was born in Chicago, Illinois to Eunice and Bill Rosen, who were professional bridge players. He attended Yale University with Ed Norton and wrote and directed political commercials for LA Mayor Dick Riordan and several other candidates. He then wrote, directed, and starred in the feature comedy "Totally Confused" (co-directed by "Dummy"'s Greg Pritikin) which was screened at the Berlin International Film. He then acted in theater in New York City before scoring a role in the unscripted series _"Amazing Race 2, The" (2002)_. He lives in Los Angeles where he is continuing to write and perform.