Daniel Craig's appearance in heels may be a cross-dressing first for the Bond hero but he follows a long tradition of gender role swapping from a tuxedo-clad Marlene Dietrich to Dustin Hoffman's Tootsie

Daniel Craig's appearance in heels, blonde wig and patterned dress for a video raising awareness of gender inequality for International Women's Day marks 007's drag debut. But cross-dressing is not, strictly speaking, new to the Bond franchise – remember the Spectre agent who attends his own faked funeral as his "widow" at the beginning of Thunderball? – and far from a novelty on the big screen.

The silent era, with its often stagey film productions, had its share of cross-dressing in the theatrical tradition, which continued into the sound era with numerous variations and embellishments. Generally speaking, girls dress as boys to get kinds of social access or agency normally denied to women while boys dress as girls to get a laugh, either by pastiching glamour (as with Craig's resolutely straight-faced turn) or travestying the appearance of an older woman – the Lady Bracknell effect.

The iconic instance of female-to-male drag came in 1930 with a tuxedo-clad Marlene Dietrich's triumphant winning over of a hostile crowd in the film Morocco. She even got a snog out of it.

Katharine Hepburn was in boy-drag for much of Sylvia Scarlett (1935), her first team-up with Cary Grant. Her role as a crook hiding from the cops was unusual – most of the time, when girls dress as boys in movies it's not to evade justice but to get access to opportunities denied them by society's sexism. Hence Elizabeth Taylor's jockeying in National Velvet (1944); Julie Andrews's female-impersonator-impersonation in Victor Victoria (1982); the soldiering of Disney's Mulan (1998); and the pursuit of education by the title characters of Osama (2003) and, of course, Yentl (1983).

For boys, the coquettish look is most often deployed as a contingent ruse – a way for a man in a tight spot to avoid recognition and trouble. Cary Grant took this tack in I Was A Male War Bride (1949) as, most famously, did Jack Lemmon and Tony Curtis in Some Like It Hot (1959), followed by Robbie Coltrane and Eric Idle in Nuns on the Run (1990) and Shawn Wayans and Marlon Wayans in White Chicks (2004) – all films requiring a hefty suspension of disbelief and revolving around the supposedly inherent absurdity of men sacrificing the high social status of their gender to pose as women.

The older-woman look can work in several ways. At its most benign, it allows a male character to take on the conventionally female persona of nurturing caregiver – see Robin Williams as Mrs Doubtfire (1993) or, at a pinch, Dustin Hoffman in Tootsie (1982). The latter role overlaps with that other classic drag persona, the battle-axe, as modelled by performers ranging from Alec Guinness in Kind Hearts and Coronets (1949) to Martin Lawrence in Big Momma's House (2000) and Tyler Perry's Madea character. It's often an excuse to showcase a kind of sexless, imperious manner, though Hoffman's performance tried to avoid the more obvious exaggerations, as is clear even from his screen test.

At its most extreme, this type can be sinister, even psychotic. In Tod Browning's 1936 horror The Devil-Doll, Lionel Barrymore posed as a devious, murderous old woman – a role that would find its most resonant echo in Psycho, quarter of a century later, with Anthony Perkins's Norman Bates taking on his mother's identity to kill.

Brian De Palma's Dressed to Kill (1980) took the approach further, earning opprobrium from some gay and transgender campaigners – a backlash that was more pronounced in the case of the transsexual killer featured in 1990's The Silence of the Lambs.

The strength of feeling such negative portrayals attract is perhaps not surprising given how few films portray cross-dressing performers, transvestites and transsexuals on their own terms. Ed Wood, bless his heart, was hardly a talent many causes would embrace for his aesthetic excellence but his 1953 film Glen or Glenda?, which drew on his own transvestite experiences, was remarkable for its sincere attempts to explore alternative lifestyles from within, rather than revelling in the flaming drag queen type showcased in films such as The Producers (1968) and La Cage aux Folles (1978). Tim Burton's 1994 biopic Ed Wood also took a relatively straight – or at least sympathetic – approach to its hero's agoraphilia.

The 70s saw more big-screen depictions of drag performance on its own terms, from the movie of The Rocky Horror Picture Show (1975) to the outré outings of Divine in such John Waters titles as Multiple Maniacs (1970), Pink Flamingos (1972) and Female Trouble (1974). And the 90s saw more attention to the reality of life for transsexuals – The Crying Game (1992) and Boys Don't Cry (1999) both featured characters with gender identities different to their biological sex – and drag performers, as sympathetically depicted in The Adventure of Priscilla, Queen of the Desert (1994), To Wong Foo, Thanks for Everything! Julie Newmar (1995) and Flawless (1999), which, Philip Seymour Hoffman's character notes, "is not Silence of the Lambs, all right?"

Recent years have seen genderqueer performer Justin Bond appearing in Shortbus as the titular sex party's den mother, not to mention Oscar hosts Anne Hathaway and James Franco (no stranger to drag) cross-dressing for a number during this year's ceremony. And on the international scene, the new-look 007 has a role model and potential partner: the heroine of The Adventure of Iron Pussy, a Thai espionage pastiche directed by arthouse wunderkind Apichatpong Weerasethakul. Check out Pussy's kick-ass entrance three minutes into this clip.

If Bond wants to fight evil while keeping his wig on, he has a lot to learn …