His many appearances on Saturday Night Live led to his role as Harry “The Hat” Gittes on the several seasons of the TV sitcom Cheers and eventually as Judge Harry Stone on another hit television sitcom Night Court. Anderson went on to appear in numerous other TV specials and shows, including 12 appearances on The Tonight Show Starring Johnny Carson. As a magician, Anderson has since toured extensively and performed many comedy/magic shows for clubs and broadcast, including Harry Anderson’s Sideshow in 1987.^{[citation needed]} In 1990, he starred in the television adaptation of Stephen King’s It as the adult Richie Tozier. From 1993 to 1997, Anderson starred in the TV sitcom Dave’s World, based loosely on the life and columns of humor columnist Dave Barry.

Together with longtime 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 (ISBN978-1-58080-086-0, 2001 reprint), this title also contains a survey of “Games You Can’t Win” told from an insider’s perspective. He appeared with Criss Angel in a TV special called The Science of Magic, later released on DVD. In November 2008, Anderson played himself on an episode of 30 Rock along with fellow Night Court cast members Markie Post and Charles Robinson.

Anderson kept a nominally low profile after Dave’s World was canceled. Tired of L.A.’s glaring spotlight, Anderson moved from Pasadena, California, to New Orleans in 2002. In the 1990s, he and his second wife Elizabeth (whom he met in New Orleans while she was bartending)^] opened a small shop in the French Quarter named “Sideshow” selling various “magic, curiosities, and apocrypha”. In 2005, he opened a nightclub in the French Quarter called “Oswald’s Speakeasy”, located at 1331 Decatur Street at the corner of Esplanade Avenue. He performed a one-man show there called Wise Guy.

In 2000, Anderson hosted the pilot for a potential revival of the classic panel game show What’s My Line? for CBS primetime. However, it was rejected later in favor of the long-running reality show Survivor.

Anderson appears in Hexing a Hurricane, a documentary about the first six months in New Orleans after Hurricane Katrina. He and his wife Elizabeth sold Oswald’s Speakeasy in October 2006. Anderson continues to present his evening show Wise Guy, which was originally developed for his theater in New Orleans.^{[citation needed]} Popular Webcomic Homestuck makes several references to Anderson, including a fictional book by Anderson called Wise Guy.