What a Drag! A Guide to TV and Movie Cross-Dressing

ABC's Work It follows the misadventures of two guys who dress as women to get jobs as pharmaceutical reps. (In these economic times, women are taking over the workforce... or so says one of the show's characters. Hmmm.)

The good news is doing drag can — and has been — a lot more interesting through the years, not to mention fun! Peruse our favorite cross-dressing characters from pop culture history, from Mrs. Doubtfire to Rudy Giuliani.