Natural around Newport, Rhode Island, Anderson was a street magician before becoming an actor. He is celebrated for the role of Judge Harold T. Stone on the 1984-1992 television series Night Court. Additionally to eight appearances in Saturday Night Live between 1981 and 1985, Anderson had the revenant guest role when con human "Harry the Hat" in Cheers, toured extensively as a magician, and did many magic/comedy shows for broadcast, including Harry Anderson's Sideshow (1987).

In the 1990s Anderson starred in the sitcom ''Dave's World'', based loosely on the life and columns of humor columnist Dave Barry. Together by owning long-period friend Turk Pipkin, Anderson wrote the book known as Games That you Potty't Lose - The Choice For Suckers, the collection of gags, cons, tricks & cozenage. Promulgated within 2001 by Burford Books (ISBN: 1580800866) this title too contains the survey of "Games You Can't Win" told from either an insider's perspective.

An extended-period Mel Torme fan, Anderson & his married woman Elizabeth presently (2005) have the little shop in the French Quarter of New Orleans named "Sideshow" selling various "magic, curiosities, and apocrypha." In the summertime of 2005, Anderson as well opened the nightspot in the French Quarter known as Oswald's Speakeasy, placed at 1331 Decatur Street, Just released Orleans.