Imagine, if you can, walking into a movie theater in 1959, at the height of the conformist Eisenhower era, to see a comedy starring matinee idol Tony Curtis, sex symbol Marilyn Monroe, and up-and-comer Jack Lemmon. It’s directed by the guy who made Sunset Boulevard almost a decade earlier, and co-written by uber-talented I.A.L. Diamond. When the film rolls, you get a black-and-white period piece set in Chicago during Prohibition, multiple scenes of gangland murder, and, oh, the two leading men spend most of the movie in drag.

From nearly every angle, Some Like It Hot is a weird, subversive picture: two hard-luck jazz musicians (Curtis and Lemmon) who witness the St. Valentine’s Day Massacre go into hiding as women in an all-female orchestra, and must navigate love and attraction–one lusts after the band’s sultry singer, played by Monroe, while the other is pursued by a wily old millionaire—all while dodging the mob. The film cuts against the cultural grain so sharply that it’s a miracle it got made at all. But that might be why it connected so forcefully with audiences and remains an unassailable American classic. It’s number 14 on the American Film Institute’s original 100 Greatest American Movies of All Time list (it clocked in at 22 on its 10th anniversary list) and it tops the AFI’s 100 Funniest American Movies of All Time ranking.

Here are 13 interesting tidbits about Some Like It Hot’s production and afterlife to help you appreciate the film even more.

1. THE QUINTESSENTIAL AMERICAN COMEDY WAS INSPIRED BY A DRY GERMAN REMAKE OF A FRENCH FARCE.

The seed that bloomed into Some Like It Hot was planted by an obscure 1951 German film, Fanfaren der Liebe (Fanfares of Love), which was a remake of an older French comedy, Fanfares d’Amour (1935). Both pictures are episodic, focusing on a pair of desperate male characters doing what they can to earn a buck. One of those schemes involves dressing like women and performing in an all-female band. Wilder and Diamond both liked that particular device—and not much else. “The humor in the German movie was rather heavy-handed and Teutonic,” Diamond said. “There was a lot of shaving of chests and trying on wigs.”

2. BILLY WILDER BUCKED ALL CONVENTION TO MAKE GANGLAND MASSACRE VITAL TO A COMEDY.

When Wilder and Diamond began writing, Wilder knew they needed to “find the hammerlock of the story, the ironclad thing in which these two guys trapped in women’s clothing cannot just take off their wigs and say, ‘I’m a guy.’” After kicking around ideas, inspiration finally hit while Wilder was driving (“Billy got a lot of his ideas driving,” Diamond said): the St. Valentine’s Day Massacre. If they set the film during the Roaring ‘20s and had their guys witness one of the era’s most brutal events, the masquerade becomes a matter, literally, of life and death. “That was the important invention that made everything else possible,” Wilder said.

3. SOME LIKE IT HOT ALMOST BOASTED MARILYN MONROE AND FRANK SINATRA.

With the plot locked down, attention turned to casting. Names thrown around for the roles of Joe/Josephine and Jerry/Daphne included Danny Kaye and Bob Hope. But Wilder quickly moved to Tony Curtis for Joe, and his choice for Jerry was Frank Sinatra. Ol’ Blue Eyes didn’t make it into Some Like It Hot, obviously. The reason why, though, depends on whose story you believe. Curtis said Wilder wanted Sinatra for Jerry/Daphne, “but he wasn’t sure Frank would be able to play it. Frank was a little bit cantankerous, and Billy didn’t want to take a chance on that.” Wilder was a bit surly himself, which makes Diamond’s version of events seem more likely: “Billy made a lunch date with Sinatra, and he went and waited and sat there, and sat there, and Sinatra never showed up. He stood Billy up.” Wilder, who became a director to control the fates of his scripts, likely wouldn’t have reacted kindly to such an affront to his authority. Sinatra was out, and Jack Lemmon was in.

4. BILLY WILDER AND MARILYN MONROE WERE THE BEST OF FRENEMIES.

The biggest piece of Some Like It Hot casting was, hands down, Marilyn Monroe in the role of singer/ukulele player/saxophonist lover Sugar Kane. It became one of her iconic roles (she’s even depicted as Sugar on a U.S. postal stamp honoring Wilder), and it was a showcase for her talents as an actor, comedian, and all-around performer. At first, Wilder thought of casting Mitzi Gaynor in the role. But when Monroe became available, Wilder jumped at working with his The Seven Year Itch star again—even if it came with some baggage. “I knew that I was going to go crazy at moments. And there were such moments, half a dozen moments,” Wilder said. “But you always tell yourself, ‘I’m not married to her, right?’ And then you come home, you have no dinner, you take a sleeping pill, and you wake up in the morning and you start again.”

Wilder recalled that Monroe showed up for early rehearsals and was great—when she remembered her lines. “She had kind of an elegant vulgarity about her. That, I think was very important. And she automatically knew where the joke was.” But with the good came the bad. During production, she would show up hours late for work, claiming to have lost her way to the studio. Wilder would have to run 80-plus takes to get one line, like “Where’s that bourbon?” or “It’s me, Sugar.” She continually deferred to her acting coach, Paula Strasberg, in the midst of arguments with Wilder. All of this put epic strains on Wilder and the cast, especially Curtis and Lemmon, who had to be perfect on every take because Wilder would use the one where Monroe was perfect, regardless of how well they performed.

The stress led Wilder to make some disparaging remarks to the press after shooting wrapped. “The question is whether Marilyn is a person at all or one of the greatest DuPont products ever invented,” the director once quipped. “She has breasts like granite; she defies gravity; and has a brain like Swiss cheese—full of holes.” Later, he added, “I have discussed this with my doctor and my psychiatrist and they tell me I’m too old and too rich to go through this again.” This prompted Monroe to call Wilder’s home and tell him to, well, fornicate himself (we’re paraphrasing here). Wilder tried patching things up, but she died a short time later. As the years went on, he softened in his view of his experience working with her. “I had no problem with Marilyn Monroe. Monroe had problems with Monroe,” Wilder said. “When it was all done, and my stomach got back to normal, it seemed well worth the agony of working with her.”

5. THE SOME LIKE IT HOT SUPPORTING CAST IS SUPER META.

Wilder looked to actors from 1930s gangster pictures to fill out the ranks of Some Like It Hot’s cops and robbers. (It was a novelty Wilder employed on Sunset Boulevard, too, from hiring silent-screen superstar Gloria Swanson as the lead to finding places for Cecil B. Demille, Buster Keaton, H.B. Warner, and Anna Nilsson.) He cast George Raft (Scarface) as Some Like It Hot’s heavy, Spats Colombo; studio player Pat O’Brien as the chief lawman; and “hey, that guy!” George E. Stone (Little Caesar) as the fink. But he didn’t stop there. Wilder also built in self-referential nods to the seminal crime movies: Near the end of the film, Spats sees a hood (played by Edward G. Robinson Jr.), flipping a coin and asks, “Where did you pick up that cheap trick?” Raft’s character Rinaldo did the same thing in Scarface. Later, in a moment of frustration, Spats goes to smash a grapefruit into one his henchman’s faces, a nod to one of the most iconic moments in The Public Enemy.

6. IF THE MEN HAD TO WEAR DRESSES, THEY WANTED TO LOOK JUST AS GLAMOROUS AS MARILYN MONROE.

Once the actors were in place, it came time to turn to more serious matters: the costumes. Lemmon and Curtis knew that if they were to pass, convincingly, as women, they’d need to look the part. And that meant good clothes. “We were very cooperative,” Lemmon says about being put in makeup and high heels, “but we did put our feet down when we wanted better dresses. They wanted us to select off-the-rack stuff from the costume department. We said we wanted dresses done by Orry-Kelly, who was doing Monroe’s costumes.” Curtis stood with Lemmon in solidarity. “I didn’t want to look like Loretta Young. You know, those high-waisted things, and I wanted a new designer dress of my own, not one of those used things. I went to Billy, and I told him Jack and I wanted Orry-Kelly dresses, too. He said, ‘Okay.’”

When I interviewed Curtis in 2004, he recalled the experience of getting fitted—and how they had some fun at Monroe’s expense: “We’re all at Goldwyn Studios and our dressing rooms are alongside of each other: Jack, me, Marilyn. And Orry-Kelly, a very prestigious-looking man, he had one of those plastic tapes. So he went in and measured Jack, and Jack came out in boxer shorts, stood in front of him and put the tape around his neck: 16, 31, 29, 18. Took all the measurements of Jack. Then he came up to me. I came out in the equivalent of Calvin Kleins. And he measured me: 13 1/2, 14, 15, 37, 29 1/2. When he finished with me, he went to Marilyn. But this is where the story came from Orry-Kelly, not from me. He goes in to measure Marilyn and she comes out in a pair of panties and a silk blouse. He stands there and measures: 29, 34, 18, goes around her [waist and rear] and he said, ‘You know Marilyn, Tony Curtis has a better looking ass than you.’ She unbuttoned her blouse, opened it, and said, ‘He doesn’t have t*ts like these!’” Curtis laughed and clapped his hands. “You can’t beat that story. She was so pissed off. I loved her for that.”

7. CURTIS AND LEMMON ARRIVED AT THEIR FEMALE PERSONAS KIND OF BY ACCIDENT.

Dressed like women, Curtis and Lemmon now needed to establish what kind of women they would be. And it was Lemmon who established the types. Curtis hemmed and hawed about leaving his dressing room first, so Lemmon took the plunge and “he was like a 20-cent tart,” Curtis said. Lemmon skipped around, talked in a high-pitched voice, and was generally bubbly and ditzy. Curtis knew the film couldn’t handle two characters like that, so he took the opposite approach: “I had to be a lady, very grand, like my mother or Grace Kelly. I held my head up, straight and high, and never went for those low-down jokes.”

8. WILDER GAVE HIS LEADING MEN VERY LITTLE TIME TO GET COMFORTABLE PLAYING WOMEN.

The last piece of the characters was their makeup. Curtis and Lemmon spent hours refining their looks. Once they thought they had it, Wilder all but pushed them into the ladies bathroom. He needed to see if it could play. “So, traipsing into the ladies’ we went, and, boy, oh, boy, the flop sweat was really flying,” Lemmon remembered. “I was scared to death. I’ve never been so embarrassed.” But it worked. No one gave them a second look. They rushed out, told Wilder, and he said, “Don’t change a thing!” But Curtis wasn’t convinced. He thought no one looked at them because they made for ugly women. So they went back into makeup, were made a little more glamorous, and went back to the bathroom. They were ID’ed immediately, so they reset to the first look.

9. TONY CURTIS HELPED BILLY WILDER REALIZE A LONG-TIME DREAM, SORT OF.

Cary Grant was Billy Wilder’s white whale. The director always wanted to work with Grant, but things never came together. In Some Like It Hot, though, Curtis got Wilder as close as possible. Besides playing Joe and Josephine, Curtis has a third role, Junior, a faux millionaire heir to the Shell Oil fortune. When it came to developing how Junior would sound, Curtis brought out his Cary Grant impersonation. “The day we were shooting that [first] scene [as Junior],” Curtis told me, “we went down on the beach and I said, ‘Billy, how am I going to play this millionaire?’ He said, ‘Well, how would you like to play it?’ I said, “Well, I do this impression of Cary Grant …’ ‘Well do it!’” So he did, and it’s quite good. “Tony Curtis gave me Cary Grant,” Wilder said. Curtis was happy with the impersonation. So was Wilder. And Grant apparently liked it, too—even if he feigned the contrary. “When Some Like it Hot finished, Billy Wilder showed it to Cary Grant,” Curtis told me. “He said, ‘Cary, how did you like Tony’s impression of you.’ Cary said [Curtis switches to his impersonation], ‘I don’t talk like that!’”

10. THE FILM’S ICONIC LAST LINE WAS ALMOST NEVER USED.

Wilder and Diamond were precise writers. But when it came time to Some Like It Hot’s punch line, they were absolutely indecisive. They got as far as Lemmon ripping off his wig and saying he can’t marry Osgood Fielding III because “I’m a man.” What comes next? Diamond suggested “Nobody’s perfect,” and Wilder said to keep it in so they could send the script to the mimeographer. But then they were really going to settle it. “We have a whole week to think about it,” Wilder said. “We thought about it all week. Neither of us could come up with anything better, so we shot that line, still not entirely satisfied.” Viewers felt entirely differently. “The audience just exploded,” Wilder said. “That line got one of the biggest laughs I’ve ever heard in the theater. But we just hadn’t trusted it when we wrote it; we just didn’t see it. ‘Nobody’s perfect.’ The line had come too easily, just popped out.”

11. SOME LIKE IT HOT WAS A LITTLE TOO HOT FOR SOME PEOPLE.

Some Like It Hot was a huge hit when it was released in 1959, but not everyone had the opportunity to see it. The film was condemned by the National Legion of Decency, a Catholic organization that acted as a watchdog for corruptive content, on the grounds that it was “morally objectionable” and “promoted homosexuality, lesbians, and transvestism.” With that designation, swaths of pious moviegoers across the nation would be compelled to stay away. But there were regional decrees against the film, too. It was banned in Kansas after United Artists refused to edit the love scene between Curtis and Monroe, while in Memphis a censorship board restricted viewing to adults-only.

12. THE FILM INSPIRED TWO (INFERIOR) STAGE MUSICALS.

Proving just how excellent Some Like It Hot and its Wilder-Diamond script are, the film was adapted for the stage twice. The first production, a musical called Sugar that centered on Monroe’s character, opened in April 1972 and ran for more than 500 performances. Some 30 years later, another musical was mounted, this time called Some Like It Hot, with Curtis cast in the role of Osgood Fielding III. It was Curtis’ first time singing and dancing on the stage, and he threw himself into it. When we talked about it 2004, Curtis had fond memories of the experience, if not the final product.

“We did in a year 273 performances and I never missed one,” Curtis said. “That was very hard work. Under the auspices that we were, the production end of it was very clumsy. So that was difficult. You couldn’t do what you did in the movie. Those scenes needed the up-close physicalness. The scene of me and Marilyn kissing, the scene with Jack and I on the train—all of that intimate stuff needed those big close-ups, and that’s what made the movie so appealing.”

13. BILLY WILDER DIDN’T THINK IT WAS THE BEST AMERICAN COMEDY EVER.

Comedy is such a subjective genre, that it’s impossible to say something is the “best.” Best to who? And based on what definition of comedy? But that didn’t stop the American Film Institute from ranking the top 100 American movie comedies, topped by Some Like It Hot. You’ll get no argument from most people, but Wilder was a bit circumspect at the honor. “I’m happy for it, but it’s not true,” he said. “It’s not the best because there is no best. It’s one of the best. It’s a good picture, and I’m proud of it. I’m happy people still like it so much.”

Additional Sources:
Nobody’s Perfect: Billy Wilder, A Personal Biography by Charlotte Chandler
Conversations with Wilder by Cameron Crowe
Billy Wilder (Cinema One series) by Axel Madsen
On Sunset Boulevard: The Life and Times of Billy Wilder by Ed Sikov
Some Like It Hot Blu-ray special features
Isn’t It Wonderful? Tony Curtis Sings and Dances in ‘Some Like It Hot,’” Lillian Ross, The New Yorker, June 3, 2002
Billy Wilder, The Art of Screenwriting No. 1, The Paris Review, Spring 1996
Personal interview with Tony Curtis, 2004