Tootsie (1982)

Film: Tootsie

Director: Sydney Pollack

Country: USA

Released: December 1982

Runtime: 116 minutes

Genre: Comedy

Studio: Mirage / Columbia

Influenced: Chris Columbus, Barbra Streisand, Mike Nichols, Sally Potter, Keenen Ivory Wayans

From Some Like It Hot to Tootsie, and Mrs Doubtfire to White Chicks, Hollywood has a strong tradition of great comedies involving cross-dressing. Initially conceived by screenwriter, Larry Gelbart, who came up with the idea for a comedy centred around a male actor who disguises himself as a woman to get a job, Tootsie underwent several revisions before becoming the classic comedy we know today. The script was developed further by Murray Schisgal and Don McGuire, and eventually it evolved into a thoughtful exploration of gender roles, as well as a hilarious romantic comedy. Legendary director, producer and actor Sydney Pollack both oversaw and starred in Tootsie, a film that played a significant role in broadening conversations about gender representation in the media and challenged Hollywood's reliance on traditional stereotypes.

Tootsie's plot revolves around the character of Michael Dorsey (Dustin Hoffman), a highly talented but difficult and unemployed actor living in New York City. Frustrated by the lack of opportunities due to his reputation, he takes a bold step: he auditions for a female role on a popular soap opera as Dorothy Michaels. Hoffman's commitment to the role was noteworthy, undergoing a remarkable transformation to portray Dorothy Michaels convincingly. This involved extensive make-up, voice training and fully immersing himself in the character. Despite an abrasive personality, Dorothy's no-nonsense charm impresses the show's producer, Ron Carlisle (Dabney Coleman), and she is hired.

Tootsie has what I would describe as a classic 80s Hollywood film soundtrack, full of cheesy but soulful songs such as It Might Be You, written by Dave Grusin and performed by Stephen Bishop. It also has a stellar cast including Hoffman, Jessica Lange, Bill Murray, Geena Davis, Dabney Coleman and Teri Garr, as well as George Gaynes (later of Police Academy fame) in a brilliant cameo as John Van Horn. Lange played the character of Julie Nichols, the co-star who Michael (as Dorothy) befriends on the show, and their strong emotional connection causes Michael to live a double life. Matters become even more complicated when Julie's father (Charles Durning) falls for Dorothy, and his and Van Horn's attraction to Dorothy create some of the film's best comic moments. 

As Dorothy, Michael achieves unexpected success and becomes a beloved character on the hospital soap opera, with his skilful portrayal of a strong, independent woman resonating with audiences. Eventually, however, as the truth about Dorothy's real identity is on the verge of being exposed, Michael has to find a way to navigate the situation and decides to deliver a heartfelt speech on live TV. Tootsie was an instant critical and commercial success, receiving ten Oscar nominations and winning one for Lange's outstanding performance. Pollack was much more deserving of a best director Oscar for Tootsie than for Out of Africa (1985). Tootsie is a film that masterfully blends humour with heartfelt moments, while also challenging gender norms long before it became overtly fashionable for Hollywood to do so.