Some like to dress up ... Tony Curtis, Marilyn Monroe and Jack Lemmon in Some Like It Hot. Photograph: EPA
Eddie Izzard recently had sceptical words for John Travolta's transvestite turn in this week's remake of Hairspray - perhaps a little harshly (this is acting, after all), even if there is an attention-seeking whiff about it. Certainly, Divine (born Harris Glen Milstead), who played the role in John Waters' original, was a little more committed to it as a way of life.
Cross-dressing, of course, is about as old as drama itself, stretching from ancient Greece through to Shakespearean comedy through to modern times. While it's never a problem finding a man wanting to drag it up when you need one, it's a lot rarer finding women pretending to be men for entertainment's sake, perhaps because the fight for their rights in the 20th century made it a far more complicated (therefore surely much more interesting) idea:
1) Jack Lemmon looks like the Joker, Tony Curtis a bit more purdy, but they're the travestying foil to the primped paragon of femininity, Monroe, in Billy Wilder's scintillating Some Like It Hot.
2) Johnny Depp looks predictably delectable as Ed Wood, the female incarnation. Evidently, it was all quite a struggle for Wood, as he painstakingly spells out for us in his maligned masterwork Glen or Glenda: "Glen, I don't fully understand this, but maybe together we can work it out!"
3) You have to work hard to find instances of women dressing as men in a film comedy, at least well-known ones. 2003's Osama, about a young girl forced to dress up as a boy under the Taliban regime, seems to be more the politicised norm.
4) Transvestism in the movies, more often than not, is a green light for a discussion of disclosure, self-expression and freedom. Almodóvar, with typical suppleness, makes it an opportunity for rapping on deceit, seduction, acting and identity in the noirish Bad Education, with Gael García Bernal a Ripley-esque antihero (and a spitter for Julia Roberts in Erin Brockovich).
5) Bugs Bunny, it has been noted, rarely passes up the opportunity to raid the dressing-up box and get a bit of lippie on, especially for the sake of messing with Elmer Fudd's mind (and Robert Crumb's too, apparently). Fugg's Siegfried doesn't exactly get the transcendental love-in he's looking for from Bug's Brünnhilde in 1957's What's Opera Doc?.
Many thanks for your ideas about rock stars who've crossed the line. Here are your favourite moments of conspicuous cameo-ing:
1) "When will I be famous?" Luke Goss once mused when he was but a callow member of razor-cheeked teen crowd pleasers Bros. Probably not when you're under a mound of prosthetics fighting Wesley Snipes in Blade 2.
2) Debbie Harry's narcotic beauty chimes well with the prophetic weirdness of David Cronenberg's Videodrome, in her first big film appearance.
3) David Bowie sports a fetching nu-metal haircut to play some kind of pixie creature in the 1980s fantasy Labyrinth. No wonder Jennifer Connelly looks so alarmed.
4) Bjork as a factory girl in Lars von Trier's Dancer in the Dark. You can tell she's working class because she has Mrs Mop-style headscarf.
5) And finally, we simply have to find room for Tom Waits and Iggy Pop's excruciating cafe conflab: the runaway highlight of Jarmusch's otherwise indulgent Coffee and Cigarettes.
