After moving to New Orleans in 2000, Anderson opened a magic shop called Sideshow on Chartres Street (now the location of the Deurty Boys art gallery) and took over the Matador club at the corner of Decatur Street and Esplanade Avenue, which he renamed Oswald's Speakeasy. He became a French Quarter fixture, walking the streets in his trademark garb of fedora, tie and suspenders.
A 2005 ad from Gambit for Harry Anderson's French Quarter club, Oswald's Speakeasy.
In a Gambit preview of Anderson's 2005 one-man show "Wise Guy," David Lee Simmons wrote, "When Anderson says he wants to bring some of the magic back to the French Quarter — where he once roamed as a street performer in the '70s before Night Court and Dave's World — he also means the magic of bygone eras. His encyclopedic knowledge encompasses vaudeville, the circus, film, TV and what he calls 'chapeaulogy' — hat culture."
Anderson and his wife rode out Hurricane Katrina and the federal floods, but he grew increasingly outspoken about the direction of the city, which he saw as a difficult place to live and work before the storm and nearly impossible afterward — particularly after the reelection of Ray Nagin as mayor in 2006. In a then-infamous New York Timesprofile, he lambasted New Orleans, saying, “This city hasn’t evolved. I just feel this place is stuck on stupid.” He subsequently moved to Asheville and lived there until his death.
Anderson's most famous role was that of a wisecracking judge on Night Court (in which he costarred with New Orleans native John Larroquette)but he also starred for four seasons on the show Dave's World, which was based on the writings of Miami Herald humorist Dave Barry. He also made guest appearances on Cheers as "Harry the Hat," a genial con man.
No information about the cause of death was released, though the Asheville Police Department said foul play was not suspected.