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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. He appeared with Criss Angel in a TV special called The Science of Magic, later released on DVD.[2]
A long-time Mel Tormé fan, Anderson gave the eulogy at the singer's funeral. Judge Stone in Night Court was also a Tormé fan; the show's creator Reinhold Weege says the fact that Anderson was also a Tormé fan was completely coincidental.[3]
Anderson moved to New Orleans in 2002. He and his second wife Elizabeth opened a small shop in the French Quarter 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 at the corner of Esplanade Avenue. He performed a one-man show there called Wise Guy.
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 Orleans, citing concerns including declining tourism to the city, the re-election of Mayor Ray Nagin, and the depressed mood prevailing in New Orleans.
In November 2008, Anderson played himself on an episode of 30 Rock along with fellow Night Court cast members Markie Post and Charles Robinson.
