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 ranking of the funniest American films of all time placed two iconic comedies at the very top, both featuring male protagonists brilliantly portraying women. These cinematic masterpieces, "Some Like It Hot" and "Tootsie," captivated audiences and critics alike with their innovative humor and memorable performances, proving the timeless comedic power of gender-bending roles.

Billy Wilder's 1959 classic, "Some Like It Hot," secured the number one spot. It stars Jack Lemmon and Tony Curtis as musicians who witness a mob hit and disguise themselves as women to join an all-female jazz band, fleeing to Florida. Their hilarious attempts to maintain their female personas while navigating romantic entanglements, particularly Lemmon's character Jerry/Daphne's blossoming relationship with a millionaire, cemented its status as a comedic benchmark. Marilyn Monroe's performance as Sugar Kane Kowal added further sparkle, making it a beloved and frequently cited example of comedic genius.

Coming in at number two was the 1982 hit "Tootsie," starring Dustin Hoffman. Hoffman plays Michael Dorsey, a talented but difficult actor who, unable to find work, reinvents himself as Dorothy Michaels and lands a role on a popular soap opera. The film masterfully explores themes of identity, gender roles, and the challenges women face in the workplace, all while delivering continuous laughter. Hoffman's nuanced portrayal of Dorothy, balancing the comedic demands with genuine character development, earned him widespread acclaim and solidified the film's place as a modern comedy classic.

Both "Some Like It Hot" and "Tootsie" demonstrate the enduring appeal of cross-dressing comedies, using the premise not just for cheap laughs but to create rich characters and explore societal norms. Their success on the AFI's list highlights how these films transcended simple disguise, offering sharp wit, clever storytelling, and unforgettable performances that continue to resonate with audiences decades later.