Had a trans/cross dressing character
Pretty progressive for a 1990's/early 2000's show.
shareBack then it was just a transvestite, no big deal. Not very "progressive" either, since transvestites had been depicted in movies and tv shows for a long time. The show's makers weren't trying to make any kind of social point, they were just going for laughs.
shareIt wasn't that progressive at all. There was a famous cross dressing character from All in the Family, and people like that were popular guests on 1980s and 1990s talk shows like the Phil Donahue Show and Jenny Jones.
Phil Donahue: https://www.youtube.com/watch?v=dDCiPBo_lhc&t=1s
Jenny Jones: https://www.youtube.com/watch?v=swG-dCqGOoM
Plus, cross dressing males was a big thing in comedy at the time (Bosom Buddies, Tootsie, Mrs. Doubtfire, The Birdcage). Designing Women even had an episode or two with a cross dresser.