Daniel Hillard, Mrs. Doubtfire
Daddy's got a brand new handbag! Tootsie will always be one of our favorite cross-dressing characters, but thanks to advances in prosthetics and makeup, Daniel Hillard's makeover was even more unbelievable. In this '90s comedy, Daniel, played by Robin Williams, pulls double duty as an out-of-work, divorced father and an eccentric English nanny named Mrs. Doubtfire. False teeth and granny glasses help him fool his ex-wife, as well as his three children.