Hollywood has a longstanding tradition of producing comedies about men dressed up as women.
Billy Wilder’s Some Like It Hot (1959), in addition to its six Academy Award nominations, was voted as the top comedy film of all time by the American Film Institute on their “100 Years… 100 Laughs” poll.
While a man in drag shouldn’t be the butt of the joke in today’s climate (nor should they ever have been), these pictures, when viewed critically, can still yield a smile to your face.
Sydney Pollack’s Tootsie (1982) is one of the most warm-hearted, least mean-spirited of these examples.
If you don’t know what to watch next, Tootsie is available to stream on Netflix. The comedy was nominated for ten Oscars, including Best Picture, Best Director, as well as Best Original Screenplay. Jessica Lange won for Best Supporting Actress.
Set in New York, Michael Dorsey (Best Actor nominee Dustin Hoffman) is an actor with a reputation for being difficult to work with.
When his friend, Sandy Lester (Best Supporting Actress nominee Teri Garr), tries out for the role of Emily Kimberly on popular daytime soap opera Southwest General, an unemployed Michael auditions as “Dorothy Michaels” and gets cast.
However, “Dorothy” becomes a star, forcing Michael into a dilemma wherein he must reconcile his success with his and Sandy’s relationship, and his feelings for costar Julie Nichols (Lange).
Tootsie is second only to Some Like It Hot on the AFI’s “100 Years… 100 Laughs,” surpassing even Stanley Kubrick’s Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb (1964), and it is preserved at the Library of Congress’s National Film Registry.
It is as romantic as it is comedic. Between Sandy and Julie, the dramatic stakes escalate the tension to a breathless climax.
Indeed, Lange defines star presence as Julie. One of the greatest actresses of her generation, she may be more recognized now for her tenure on FX’s American Horror Story (2011-), but she hits her marks as the infamously Method Hoffman’s love interest.
She can be funny without coming at the expense of her pathos, and you can’t help but fall for Julie, too.
Aside from the film’s questionable sexual and gender politics, Tootsie also suffers from Hoffman’s presence in it. After all, he was a name named as part of the #MeToo movement.
Not to mention, he made self-congratulatory comments during an interview about how he needed to play “Dorothy Michaels” to learn sexism is a thing.
Again, Tootsie is for the critical consumer. If you can look past the era it represents, you will find yourself taken by its romance and its wit. It is a movie with both a heart and a mind, which is what makes it as comforting for the soul as falling in love itself.