One of the nice things about seeing this film in a theatre is listening to people actually laughing at the jokes in a 58 year old movie. The story is timeless, and so is the dialogue. Jack Lemmon is especially funny - his switches back and forth from "I'm a girl" to "I'm a boy" are the icing on this gender-switching farce. His interactions with the unappreciated Joe E. Brown are also priceless bits of comedy.
It's also fun to watch Billy Wilder incorporate references to old gangster films of the 1930s. Witness Edward G. Robinson, Jr. (as Johnny Paradise) mimic George Raft's Guino Rinaldo in Scarface with his coin-tossing antics. "Where did you pick up that cheap trick?" Raft asks. According to the AFI Catalog, Wilder wanted Edward G. Robinson to appear in the film, but Robinson declined. He despised George Raft, and had vowed never to work with him again. One wonders if he enjoyed watching his son gun down Robinson late in the film!
Another visitor from the land of the 1930s gangster picture is Pat O'Brien, who often played a good guy in those early films. Here he is again on the side of law and order as Mulligan, the police detective investigating the massacre. He's got some nice repartee with both Raft and Nehemiah Persoff, making his relatively small role memorable.
Tony Curtis had some troubles with doing a falsetto (his lines as Josephine are partially dubbed by Paul Frees), but he had no problems doing his Cary Grant imitation (Grant would later jokingly tell Billy Wilder "I don't talk like that!!!" (The Guardian)). Curtis came up with the idea of doing Shell Oil Junior as Mr. Grant, rather than just talk like Joe. Wilder, who had always wanted to work with Mr. Grant, was amused. Curtis, who later did a tribute to Mr. Grant for TCM, stated that he wanted to imitate Mr. Grant because it implied culture, and because he had always wanted to work with Cary Grant.
The film was originally to be shot in color, but the makeup that the men wore was just too outlandish in color. Though Marilyn Monroe had expected (and wanted) to appear in a color film, Billy Wilder showed her the color rushes - she agreed to the switch to black and white.
When you watch this film today, you wonder how Mr. Wilder and Mr. Diamond were able to pull of this very daring film (the film was condemned by the Catholic Church's Legion of Decency). Yet, despite its edginess, audiences embraced it when it opened (see this TCM Article for more on the film's release). Very loosely based on a German film (Fanfaren Der Liebe) in which two musicians cross-dress (among their many wardrobe changes) to get jobs, Wilder and Diamond added the 1930s gangster angle. Frank Sinatra and Mitzi Gaynor were considered for the parts of Jerry/Daphne and Sugar. At one point, Wilder wanted Danny Kaye and Bob Hope for Jerry and Joe, but ultimately decided on Curtis and Lemmon.
For all those Star Trek fans out there, watch for Grace Lee Whitney (in the unbilled role, Rosella). She's very obvious in the party scene on the train to Florida.
Though it did well at the box office, it didn't garner all that many awards - Golden Globe Awards for both Jack Lemmon and Marilyn Monroe (the Globe has awards for acting in comedies, which surely helped against the juggernaut of Ben Hur). History has been kinder the to the film, and besides being first on the AFI comedy list, it is also #22 on the AFI's 100 Years, 100 Films, 10th Edition, as well as #48 on AFI's 100 Greatest Quotes of All Time. I'm going to leave you with that quote. Quite frankly, the line IS perfect!