Believe it or not, there was once a time when movies about dudes dressing up as ladies weren't uniformly terrible. That time was 1959, and the movie was Some Like It Hot. Despite producing wretched offspring like Juwanna Mann and She's the Man, this screwball farce is hailed as a comedy classic -- indeed, according to some people, the greatest comedy in movie history. But why? How has it earned such a reputation? Let's fill a hot-water bottle with whiskey and investigate.
Some Like It Hot earned Oscar nominations for best actor (Jack Lemmon), director, adapted screenplay, cinematography, set direction, and costume design, though it only won for costume design. It won Golden Globes for best picture (musical or comedy), best actor (Lemmon), and best actress (Marilyn Monroe). In 1989, when the Library of Congress began its National Film Registry, Some Like It Hot was in the first batch of movies to be selected for preservation. The American Film Institute put it at No. 14 on its 1998 list of the best American movies ever made, dropping it down to No. 22 on the 2007 revised list. Even more significant: When the AFI made its list of the funniest movies of all time, Some Like It Hot got the No. 1 spot. That's right, the American Film Institute considers this THE funniest movie.
Men have been dressing up as women for purposes of comedy for as long as there has been comedy, first on stage and later in films. But for the most part, the early uses of this comic device in mainstream entertainment had strictly nonsexual overtones: men disguising themselves as nuns or spinster aunts, that sort of thing.
Some Like It Hot represented a shift toward a more risqué brand of humor. In this film, the male characters dress as women for a practical reason -- they need to hide from mobsters -- but in the process become entangled with actual, beautiful women, to whom they are attracted. Marilyn Monroe innocently and playfully snuggles up in bed with Jack Lemmon because she thinks he's a girl; Lemmon, meanwhile, must exercise extraordinary (and hilarious) restraint not to take advantage of the situation.
The scenario of a man disguising himself as a woman and thereby being privy to the intimate conversations of the women around him, and all the sexual titillation that goes with it, is commonplace now. (The reverse, with a woman dressing as a man, is less common but still viable.) Here, I'll list five off the top of my head: Sorority Boys, White Chicks, Big Momma's House, Tootsie, and Just One of the Guys. But before Some Like It Hot, cross-dressing comedies almost always left the sexual tension out of it.
Except, that is, for the 1935 French movie Fanfare d'Amour (Fanfare of Love) or its 1951 German remake, Fanfaren der Liebe. Some Like It Hot was based on these -- or, more exactly, on the original story on which the 1935 film was based. Billy Wilder and his co-writer, I.A.L. Diamond, added the important element of the gangsters, and improved upon the other little-seen versions in other ways. As far as most of America knew, what was happening in Some Like It Hot was wildly new. Hugh Hefner called it "sexually revolutionary," and Hugh Hefner is a man who knows about sexual revolutions.
Given its naughty content, it's a little surprising that Some Like It Hot didn't have much trouble getting made. Billy Wilder had enjoyed a decade of tremendous success with hits that included Sunset Boulevard (1950), Sabrina (1954), The Seven Year Itch (1955), The Spirit of St. Louis (1957), and Witness for the Prosecution (1957). He'd been nominated for seven Oscars in the 1950s alone, four as director and three as writer. Marilyn Monroe, his star from The Seven Year Itch, was already a Hollywood icon. Tony Curtis was a rising star with an Oscar nomination for The Defiant Ones (1958). Jack Lemmon had won a supporting actor Oscar for Mister Roberts. Joe E. Lewis, in the pivotal role of the millionaire who falls in love with a dolled-up Lemmon, was an old-school comedy legend. All the elements were in place for a big hit.
Monroe's temperamental behavior was problematic and is now the stuff of legends, but the film still got made. The setback with the most far-reaching effects was more prosaic: Wilder couldn't shoot the movie in color, as he had planned, because the makeup Lemmon and Curtis wore as women looked greenish on film.
Two unemployed musicians in 1929 Chicago witness a mob hit and get out of town the only way they can: by disguising themselves as women and taking a gig in Florida with an all-girl jazz band. (What, you would do something else?)
What it Influenced
Some Like It Hot was the highest-grossing comedy in movie history up to that point, and one of the top films of 1959 (after Ben-Hur and North by Northwest). Unlike some classics, its reputation as a great comedy emerged almost immediately, not years later. So while the film's cross-dressing premise and some of its plot points are as old as Shakespeare, it's fair to say that most men-in-drag comedies that came after Some Like It Hot were influenced by it.
Many of them seem to have adopted its template, in fact: men disguise themselves as women; almost chicken out but are mesmerized by one of the lovely ladies they'll get to associate with; become privy to the inner secrets of womanhood because they're considered equals. One of the disguised men will give his lady friend romantic advice; often, the man she's pursuing is, unbeknownst to her, the very "girl" who's telling her how to woo him. The disguised man who is least attractive as a woman will have to fend off the comical advances of a lovestruck man who finds "her" beautiful. The truth comes out eventually, and the female lead doesn't seem to mind that she confided all her secrets in a girlfriend who turned out to be a guy. In fact, she's in love with him!
Some Like It Hot was also one of the nails in the coffin of the Production Code. This was the Motion Picture Association of America's method of self-censorship, instituted in the 1930s to keep the government from getting involved. By the 1950s, Hollywood was growing restless with the Code, and even after updates were made to reflect the changing times (you were allowed to depict interracial romances now!), there were still a lot of restrictions.
So filmmakers started pushing back. Adhering to the Code was voluntary, technically, but it had long been the accepted wisdom that a movie released without the MPAA's seal of approval would be a flop, either because theaters wouldn't play it, or audiences wouldn't watch it, or both. But the studios gradually began to suspect that this was no longer the case. Otto Preminger's The Man with the Golden Arm (1955), with its graphic depiction of drug use, couldn't get MPAA certification -- so United Artists released it without one. The film was a commercial and critical success and the recipient of three Oscar nominations. Skipping the MPAA approval process didn't necessarily spell doom after all.
The MPAA rejected Some Like It Hot because of its double entendre, cross-dressing, vague allusions to homosexuality, and general naughtiness. The studio (United Artists again) released it anyway, and it was, as previously noted, a smash hit. More and more people in Hollywood started saying, "Wait, tell me again why we even have a Production Code...?" After more and more films pushed the limits in the 1960s, the Code was finally abandoned and replaced with the rating system familiar to us now.
What to Look For
Sometimes I think lists like the AFI's do more harm than good to a film's reputation. With Some Like It Hot at the top of the "funniest movies" list, someone watching it for the first time might do so expecting it to make him laugh more than any movie he's ever seen. That's a pretty tall order. You should not expect that.
One of the fascinating aspects of the film is this dichotomy: it's surprisingly racy for its day, and yet at the same time remarkably tame. The leader of the band, Sweet Sue, laments losing two musicians: "Here we are, all packed, ready to leave for Miami, and what happens? The saxophone runs off with a Bible salesman, and the bass fiddle gets herself pregnant!" Pregnant! Even the word was uncommon in movies of that era, and the notion of out-of-wedlock pregnancy was specifically forbidden by the Production Code. And yet by modern standards, that's barely even a PG-rated reference.
The movie is packed with stuff like that. It's all about sex ... and the word "sex" is used only once, as a synonym for "gender." There is no profanity or nudity, of course. When Curtis jostles Lemmon and upsets his fake boobs, Lemmon calls them his "chests." (One assumes "breasts" would have been crossing the line.)
It's well known that when Curtis's character poses as a wealthy oil baron, he's impersonating Cary Grant. Grant was Tony Curtis' idol, as he discussed at length for this Turner Classic Movies tribute. Immediately after shooting Some Like It Hot, Curtis got to work with Grant in the comedy Operation Petticoat. Grant has been widely quoted as saying, "I don't sound like that!" when he saw Some Like It Hot, but you have to assume he took it all in good humor.
The film's Mafia angle, while not the focus of the story, gets a few amusing inside jokes of its own. The big boss is named Little Napoleon, a reference to Little Caesar (1931), the gangster film that made Edward G. Robinson a star. There's also a moment when one of the goons is about to smash a grapefruit in someone's face before stopping himself, a nod to the notorious moment in The Public Enemy (1931) when James Cagney does that to Jean Harlow.
What's the Big Deal?
As we've mentioned before, when a comedy is a Big Deal, the reason is usually just that it made a lot of people laugh. Some Like it Hot certainly did that, and it continues to do so now -- a fairly impressive feat, given how much society, movies, and comedy have changed in the past 52 years. (I can provide anecdotal evidence, anyway, that it's still funny: I re-watched it last week and laughed quite a bit. Jack Lemmon's huge Nicholson-as-the-Joker grin never ceases to amuse me.) But the film also helped nudge the useless Production Code out of the way, added a few more watts to Monroe, Lemmon, and Curtis' star power, and provided an archetype for dozens of cross-dressing comedies to follow. And it's a fact that the movie's closing line is one of the best closing lines in movie history. If you don't know it, I'm not gonna spoil it for you.
Further reading: The original reviews from The New York Times and Time magazine are enlightening. Notice how the Time review, in particular, seems focuses on Marilyn Monroe's physical appearance. Roger Ebert, in his 2000 appraisal of the movie, is likewise mostly interested in Monroe as a scene-stealer.