After witnessing a Mafia murder, slick saxophone player Joe and his long-suffering buddy, Jerry, improvise a quick plan to escape from Chicago. Disguising themselves as women, they join an all-female jazz band and hop a train bound for sunny Florida. While Joe pretends to be a millionaire to win the band’s sexy singer, Sugar, Jerry finds himself pursued by a real millionaire as things heat up and the mobsters close in.
When you just happen to witness the 1929 St. Valentine’s Day massacre in Chicago and barely escape with your lives, your days are numbered—unless you can come up with a disguise so good that not even the mafia can trace you. Joe and Jerry are two charming louts who happen to play in jazz bands—so when the only faraway job they can get is to join an all-girl band on the way to Florida, well, shave your legs and stuff your bras, gentlemen.
Being (presumably) heterosexual men, they’re a little overcome at the plethora of scantily-clad, beautiful women surrounding them: none more appealing than Sugar Kane. While “Josephine” pulls off a minor yacht heist to woo Sugar, posing as the millionaire “Shell Oil Junior,” Jerry—who goes by Daphne now—leans into his new life as a woman. But something is up with these ladies, and the mob has noticed, too.
Marilyn Monroe as Sugar Kane
Marilyn Monroe is the only person, I think, who could have played Sugar. When I first saw it as a young teen, I hadn’t realized that besides being ridiculously gorgeous, she was also funny. Her comedic timing is as impressive as that famous sheer dress she wears in Florida.
Jack Lemmon as Jerry/Daphne
The way Jack Lemmon plays Daphne could have gone so wrong, but his joy and outrage as he experiences life as a woman is the biggest delight. His irresistible performance runs the gamut from gung-ho curiosity to fully and comfortably embracing his feminine side. It’s played for laughs, of course, but there’s something wholesome about the way he settles into expressing himself as a woman.
Tony Curtis as Joe/Shell Oil Junior/Josephine
Joe is the hornier of the two male musicians, who finds this whole “being a woman” business to be a grim reality of running from the mob. Still, though, it’s a good opportunity to find out that Sugar is looking for a millionaire who wears glasses. It’s also not going to stop him from creating an identity as a millionaire from Shell Oil, declaring dramatically that he hopes someday, he can feel something for a woman. Maybe Sugar is up to the challenge…
Couch-Sharing Capability: Demand It
This movie fills me with the same kind of joy that Magic Mike XXL does. Okay, not exactly the same, but it is a movie about non-judgmental male friendship that takes place during a road trip, and has that same irrepressible cheerfulness. There’s a theme of acceptance and tolerance that strikes me as very ahead of its time for 1959. It’s the kind of movie that you can watch with your grandpa or your girlfriends—the humor holds up.
It also has the single best closing line I have ever seen in a movie.
Recommended Level of Inebriation: I Want Another Cup of “Coffee”
Alcohol is strictly verboten in the movie, but are we going to let a little thing like Prohibition or Sweet Sue discourage us? I think not. Grab the champagne and serve it in vintage teacups—you’ll know why soon.
Use of Your Streaming Subscription: Yes
If you haven’t watched this before, I insist that you queue it up as soon as possible. There’s truly something for everyone: wit, wordplay, laughs, aesthetics and a killer soundtrack. If you don’t walk away from this movie wanting to put on a beaded gown and go out dancing with your friends to a big brass band, I won’t know what to do with you.