Tootsie (1982)

Michael Dorsey, an unsuccessful actor, disguises himself as a woman named Dorothy Michaels to land a role on a trashy hospital soap opera. As Dorothy, Michael begins to learn about the challenges women face and becomes a beloved character on the show. Along the way, he navigates complicated relationships with his best friend Jeff, his love interest Julie, and his friend Sandy. Eventually, Michael's deceit is exposed on live television, leading to personal and professional consequences.