The first time I watched Some Like It Hot, I thought it was funny. The second time I watched it, I thought it was surprisingly clever. The third time I watched it, I saw it for the genius it truly is. I’ve always believed that Billy Wilder is one of the great comedy screenwriters of all time, but it wasn’t until Some Like It Hot that I had clear, definitive proof. Originally pulled from another film, Fanfare of Love, that follows two down-on-their-luck musicians who dress in drag for the sake of gig, Some Like It Hot adds an interesting element: the two musicians are on the run from a gangster who they witnessed killing his rival.

In Prohibition-era Chicago, Joe and Jerry are two friends who perform with a jazz ensemble in a speakeasy. When the police raid the place, Joe and Jerry narrowly escape the scene only to witness the speakeasy’s owner, “Spats” Colombo, gunning down his rival and the man who tipped off the police, “Toothpick” Charlie. Without other options, Joe and Jerry pose as women so they can tour with the all-female band, Sweet Sue and her Society Syncopators, and become obsessed with the band’s singer and ukulele player, Sugar Kane. Joe goes by Josephine and Jerry goes by Daphne, and both struggle to avoid giving themselves away and not make passes at Sugar. In Miami, Joe adopts another persona, Junior, the heir to the Shell Oil company in an attempt to woo Sugar, while an older millionaire named Osgood attempts to woo Daphne. Joe uses Jerry as Daphne to occupy Osgood while he uses Osgood’s yacht to spend a night with Sugar. When both men return to their room, Jerry reveals that Osgood proposed and Daphne said “yes”. Meanwhile, a secret meeting between the country’s gangsters under the name “Friends of the Italian Opera” is happening at the same hotel, and of course, Spats is there. Joe and Jerry are discovered, even in their disguises, and must escape. Seeing his last chance, Joe as Josephine jumps onstage and kisses Sugar, causing her to realize that Josephine and Junior are the same person. Jerry as Daphne convinces Osgood to bring them on his yacht as he sets sail so they can escape. In a last ditch effort to get out of marry Osgood, Jerry, as Daphne makes the following argument:

Jerry: We can’t get married at all!

Osgood: Why not?

Jerry: Well, in the first place, I’m not a natural blonde.

Osgood: Doesn’t matter.

Jerry: I smoke! I smoke all the time!

Osgood: I don’t care.

Jerry: Well, I have a terrible past. For three years now, I’ve been living with a saxophone player.

Osgood: I forgive you.

Jerry: I can never have children!

Osgood: We can adopt some.

Jerry: But you don’t understand, Osgood! I’m a man!

Osgood: Well, nobody’s perfect.

Typing the punchlines out will never be as funny as witnessing the actual film, so forgive me for that whole bit there, but it’s such a famous bit of dialogue that I didn’t see any harm in it. Anyway, it’s one of the few movies I would argue that’s “laugh out loud” funny. So much so, that the scene where Jerry explains his engagement to Osgood to Joe had to be redone and the dialogue spaced out because the first audiences were laughing over the jokes. Things behind the scenes, however, were not as humorous. Marilyn Monroe, who plays Sugar, showed up late to set frequently, delaying filming, and had to do multiple takes on simple scenes because she couldn’t remember her lines. One line, “It’s me, Sugar”, required 47 takes before she got it right. Legend has it that Tony Curtis (Joe) and Jack Lemmon (Jerry) placed bets on how many takes any particular scene would require. It’s incredibly heartbreaking to know how much her life and addiction was taking a toll on her, but it’s also impressive the performance she could bring to the table despite all of that.

That was a surprisingly depressing note to end on, so against my better judgment, here’s another snippet of dialogue where Jerry as Daphne attempts to hit on Sugar with a private drinking party, hoping to reveal he’s an eligible man:

Daphne: No lights. We don’t want anyone to know we’re having a party.

Sugar: But I might spill some.

Daphne: So spill it! Spills, thrills, laughs and games. This may even turn out to be a surprise party.

Sugar: What’s the surprise?

Daphne: Not yet.

Sugar: When?

Daphne: Better have a drink first.

Sugar: There. That’ll put hair on your chest.

Daphne: No fair guessing.

Bonus Review: Cat Ballou

Much like Some Like It Hot, Cat Ballou is riotously funny movie. Perhaps with a little more pathos than the former, but it doesn’t cut short the comedy for it. There are actually a small handful of excellent Western comedies, including Blazing Saddles and the made-for-television film, Evil Roy Slade (which gets no other mention in my Top 100, though it probably should…Dick Shawn is hilarious as a singing, scatting, guitar-strumming cowboy). Cat Ballou, however, is special. The two leads are not well-known for comedy – Jane Fonda more so than Lee Marvin, perhaps, but both are more dramatic types.

Catherine Ballou (Jane Fonda) is a schoolteacher who returns home to her father’s ranch only to discover that the Wolf City Development Corporation is threatening Frankie Ballou (John Marley) to give up his ranch so they can use it for their own purposes. When Frankie refuses to give in to their demands, they send the killer, Tim Strawn (Lee Marvin), to do what he does best. Cat hires the notorious sharpshooter, Kid Shelleen (also Lee Marvin), in an attempt to save her father, but Shelleen is revealed to be a drunken buffoon – still a crack shot, but past his prime. After the murder of her father, Cat Ballou demands justice from the town of Wolf City, but she doesn’t get it. With a ragtag team, she decides to take matters into her own hands, becoming a notorious outlaw. When she accidentally kills the head of the Wolf City Development Corporation, she finds the town now all too willing to pursue justice. It’s hard out there for a woman.

This Western Comedy is equal parts hilarious, dramatic, and action-packed, and Lee Marvin shines as the uproarious Kid Shelleen, and as his own brother, Strawn. It’s a shame that this is the role Lee Marvin gets accolades for, but it’s also well-warranted. There’s also Nat King Cole and Stubby Kaye as two banjo-wielding minstrels to narrate the story, which is a fun play on the Greek chorus storytelling device and an unusual comedic addition. Cat Ballou is great, especially for a first-time watch, because you’re not quite sure what you’re going to get until you get it.