Born in Newport, Rhode Island, Anderson was a street magician before becoming an actor. He is famous for the role of Judge Harry Stone on the 1984-1992 television series Night Court. In addition to eight appearances on Saturday Night Live between 1981 and 1985, Anderson had a recurring guest role as con man "Harry the Hat" on Cheers, toured extensively as a magician, and did several magic/comedy shows for broadcast, including Harry Anderson's Sideshow (1987). Anderson starred in the 1985 Tales from the Darkside episode 'All a Clone by the Telephone'.
In 1990 he starred in the successful television adaptation of Stephen King's IT directed by Tommy Lee Wallace. From 1993 to 1997, Anderson starred in the sitcom Dave's World, based loosely on the life and columns of humor columnist Dave Barry. Together with long-time friend Turk Pipkin, Anderson wrote a book called Games You Can't Lose: A Guide for Suckers, a collection of gags, cons, tricks and scams. First published in 1989 (ISBN 1-58080-086-6—2001 reprint), this title also contains a survey of "Games You Can't Win" told from an insider's perspective.
A long-time Mel Tormé fan, Anderson and his wife Elizabeth once owned a small shop in the French Quarter of New Orleans named "Sideshow" selling various "magic, curiosities, and apocrypha." In the summer of 2005, Anderson also opened a nightclub in the French Quarter called Oswald's Speakeasy, located at 1331 Decatur Street. He performed a one-man show there called Wise Guy. Harry has a son, Dash, and a daughter, Eva, from a previous marriage to Leslie Pollack.
Anderson appears in "Hexing A Hurricane", a documentary about the first six months in New Orleans after Hurricane Katrina.
In August 2006, Anderson and his wife announced their decision to leave New Orlean. The Andersons have purchased a home in Asheville, North Carolina, sold their house in New Orleans and Oswald's Speakeasy as of October 2006.
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