The American Film Institute in the year 2000 asked a jury of film-industry leaders to list the funniest movies of all time. The top two movies on the list were films in which men played the role of women. Name these films.

The American Film Institute's 2000 special, "100 Funniest American Films," offered a fascinating look into what the film industry considers peak cinematic humor. What makes the top of this prestigious list particularly intriguing is that both number one and number two spots were claimed by comedies where male actors famously donned dresses and adopted female personas. This comedic device, often involving mistaken identity and social satire, proved to be an undeniable recipe for success in the eyes of the AFI's jury.

Topping the list was Billy Wilder's 1959 masterpiece, Some Like It Hot. Starring Jack Lemmon and Tony Curtis as musicians on the run from the mob, who disguise themselves as women to join an all-female band, the film is a masterclass in farce, sharp dialogue, and unforgettable performances. Marilyn Monroe's iconic role as Sugar Kane further cemented its status, making it a beloved classic that expertly balances slapstick with genuine heart, pushing boundaries for its era while remaining universally hilarious.

Just behind it, at number two, was Sydney Pollack's 1982 hit, Tootsie. Dustin Hoffman delivers a career-defining performance as Michael Dorsey, a struggling actor who reinvents himself as Dorothy Michaels to land a role on a soap opera. The film brilliantly explores themes of gender roles, professional integrity, and the challenges women face in the workplace, all while delivering consistently witty humor and memorable character development. Both films demonstrate the timeless comedic power of actors fully committing to the art of transformation, proving that a well-executed identity swap can lead to legendary laughter.