Tootsie (1982)

"Tootsie" is a groundbreaking comedy that tackles themes of identity, gender roles, and love with surprising depth. Michael Dorsey, a talented but difficult actor, resorts to cross-dressing to find work and support his friend's play. As Dorothy Michaels, he unexpectedly finds success, captivating audiences and inspiring women to embrace their independence. Dorsey's transformation into Dorothy blurs the lines between his true self and his female persona, setting the stage for a complex and hilarious exploration of relationships. While often categorized as a comedy, "Tootsie" deserves a place among the best romance movies because it fundamentally explores the complexities of love, desire, and connection. Dorsey's journey through Dorothy is not just about finding employment; it's about navigating the world of human connection from a fresh perspective. He falls in love with a co-star (Jessica Lange) while in drag, and the film delves into the emotional challenges and genuine feelings that arise from this unconventional connection. The film's core question, "Can a man truly love a woman while pretending to be one?", offers a truly unique, thought-provoking and moving romantic journey, showcasing the power of empathy and genuine human connection.