Tootsie (1982)

Michael Dorsey is an unemployed actor with an impossible reputation. In order to find work and fund his friend's play he dresses as a woman, Dorothy Michaels, and lands the part in a daytime drama. Dorsey loses himself in this woman role and essentially becomes Dorothy Michaels, captivating women all around the city and inspiring them to break free from the control of men and become more like Dorsey's initial identity. This newfound role, however, lands Dorsey in a hot spot between a female friend/'lover,' a female co-star he falls in love with, that co-star's father who falls in love with him, and a male co-star who yearns for his affection.—Bryan Kuniyoshi