
I usually like to throw curveballs here at the Comedy Palace. I try not to cite the most obvious examples or post the most famous clips. But there are times when there's no way around it; I'm not going to talk about Abbott and Costello and not highlight "Who's on First." Similarly, in considering the greatest cross-dressing comedies, my conclusion is that the first two you think of actually are the two greatest -- by miles.
Cross-dressing comedy gold begins, of course, with Some Like it Hot, Billy Wilder's 1959 masterpiece. It's been widely hailed (including by the American Film Institute) as the best film comedy of all time. In my view, it's not quite that, but it does have a number of things going for it. The screenplay, by Wilder and I.A.L. Diamond (no relation), crackles with great and funny dialogue, and everyone in the remarkable cast (Tony Curtis, Jack Lemmon, Marilyn Monroe, George Raft, Pat O'Brien, Joe E. Brown) is at the top of his or her game.
The comedic centerpiece of the film is Jack Lemmon's portrayal of Jerry/Daphne. Just as Lemmon throws himself into the role of Jerry, Jerry becomes Daphne with hilarious abandon. The great thing about the Daphne character is the indignant conviction Lemmon brings to her. As the ruse progresses, he ceases to be a man impersonating a woman, and begins responding to events not as Jerry but as Daphne.
Jerry's increasing comfort in Daphne's skin carries the film to its delectable conclusion -- and to possibly the best last line in the history of American cinema:
Some Like it Hot successfully defended its status as the cinema's greatest cross-dressing comedy until 1982. Sydney Pollack's Tootsie (screenplay by Larry Gelbart, Murray Schisgal, Barry Levinson, and Elaine May) operates on a similar premise: Down-on-his-luck actor Michael Dorsey (Dustin Hoffman) becomes Dorothy Michaels because he needs the work (though he's not evading villains, like Lemmon and Curtis in Some Like it Hot).
What makes Tootsie a greater comedy than Some Like it Hot is that it takes the cross-dressing bit beyond laughter, and uses it to make worthwhile points about gender in society. The characters in Some Like it Hot aren't there to learn anything; it's simply an expertly-crafted, beautifully performed comic caper. In Tootsie, Michael Dorsey's pragmatic decision to don a dress and make-up becomes an unintentional social experiment along the lines of Black Like Me. Once he sees, firsthand, how women are treated by men -- including him -- he grows. None of this social comment would be effective, though, if Tootsie were not also one of the funniest films of all time.
And that's pretty much it. There have been other cross-dressing comedies of note, but they have ranged from admirable misfires (La Cage Aux Folles, Mrs. Doubtfire, and at least two film versions of Charley's Aunt) to pallid camp (The Adventures of Priscilla, To Wong Foo, and certain efforts from Ed Wood and John Waters). Then there are a few films in which women pretend to be men (Yentl, Victor/Victoria, and Just One of the Guys, none of which, in my opinion, qualifies as a great comedy).
Jerry's increasing comfort in Daphne's skin carries the film to its delectable conclusion -- and to possibly the best last line in the history of American cinema:
Some Like it Hot successfully defended its status as the cinema's greatest cross-dressing comedy until 1982. Sydney Pollack's Tootsie (screenplay by Larry Gelbart, Murray Schisgal, Barry Levinson, and Elaine May) operates on a similar premise: Down-on-his-luck actor Michael Dorsey (Dustin Hoffman) becomes Dorothy Michaels because he needs the work (though he's not evading villains, like Lemmon and Curtis in Some Like it Hot).
What makes Tootsie a greater comedy than Some Like it Hot is that it takes the cross-dressing bit beyond laughter, and uses it to make worthwhile points about gender in society. The characters in Some Like it Hot aren't there to learn anything; it's simply an expertly-crafted, beautifully performed comic caper. In Tootsie, Michael Dorsey's pragmatic decision to don a dress and make-up becomes an unintentional social experiment along the lines of Black Like Me. Once he sees, firsthand, how women are treated by men -- including him -- he grows. None of this social comment would be effective, though, if Tootsie were not also one of the funniest films of all time.
And that's pretty much it. There have been other cross-dressing comedies of note, but they have ranged from admirable misfires (La Cage Aux Folles, Mrs. Doubtfire, and at least two film versions of Charley's Aunt) to pallid camp (The Adventures of Priscilla, To Wong Foo, and certain efforts from Ed Wood and John Waters). Then there are a few films in which women pretend to be men (Yentl, Victor/Victoria, and Just One of the Guys, none of which, in my opinion, qualifies as a great comedy).
It's not exactly a cross-dressing comedy, but Carl Reiner's All of Me (1984) deserves acknowledgment in this discussion. Steve Martin's landmark performance -- as a man who has a woman (Lily Tomlin) occupying half his body -- does belong in the pantheon with Lemmon in Some Like it Hot and Hoffman and Tootsie. As gender commentary, All of Me is not as sharp as Tootsie, but it is one of the exceptional comedies of the Eighties, and a gem in the consistently remarkable careers of Reiner, Martin, and Tomlin.
I will also award one Honorable Mention to The Birdcage (1996), which is almost a great comedy. It's an American remake of La Cage Aux Folles, and it improves upon the original in nearly every way. It benefits from the collaborative fireworks between Mike Nichols and Elaine May (who provided the solid direction and the sparkling screenplay, respectively). It also features Nathan Lane, unquestionably one of the best stage performers of our time, in his only great film performance to date. There's also fine supporting work by Robin Williams, Hank Azaria, Dianne Wiest, and Gene Hackman.
The problem with The Birdcage -- as with the original La Cage -- is that the treatment of Lane's character, Albert (or Albin in the original) is just too cruel. His lover and his lover's son think very little of asking Albert to either disappear or submerge his identity in the presence of the prospective in-laws. It sounds like a reasonable comic premise, but when you watch the film, it's just too much. I don't know why Nichols and May couldn't find a little more nuance here, but for whatever reason, the characters become difficult to sympathize with after we see the way they treat Albert.
Some have criticized The Birdcage for its depiction of Albert and Armand (Williams) as an apparently sexless gay couple, but to me this is preposterous. Yes, Albert and Armand come across more as fey roommates than ardent lovers, but we've seen heterosexual couples depicted this way for centuries and it doesn't seem to have bothered anyone. And would you enjoy The Birdcage more if it featured a nice long take of Nathan Lane and Robin Williams sucking face? For what it's worth, GLAAD had no problem with the film, praising it for "going beyond the stereotypes to see [Albert's] depth and humility," and noting that the film "celebrates differences and points out the outrageousness of hiding those differences."
The Birdcage also has a hilarious last line, worthy of the last line in Some Like it Hot. It comes at the end of this, the climactic sequence, in which the conservative Senator Keeley (Hackman) avoids the paparazzi by sneaking out of Armand's drag club dressed as a woman:































