A history of actors in drag -- We look back at memorable performances from Charlie Chaplin, Dustin Hoffman, Tim Curry, and others


John Travolta

For almost as long as there have been men and women, there have been men dressing as women. The Greeks kicked it off, donning womanly masks when the theater was deemed too unseemly for the real thing. And the grand tradition continues! But as John Travolta preps to wow us as Edna Turnblad in Hairspray, director Adam Shankman insists, ”She’s not in drag. She’s a woman.” Confused? EW drags out a timeline of TV and film gender benders to (not quite) straighten things out.

1914-15 Just as he picked up a hat and cane for his Little Tramp period, silent-film comic Charlie Chaplin went femme in The Masquerader, A Busy Day, and A Woman.

1948-55 Milton Berle‘s self-titled, vaudeville-style show made him TV’s first star. Uncle Miltie would also be proud to be remembered as the original Nip/Tuck.

1959 On the lam from the Mob, Jack Lemmon and Tony Curtis hid in an all-girl band in Some Like It Hot — but these ”ladies” were no match for Marilyn Monroe!

1970-74 Flip Wilson‘s sassy Geraldine paved the way for dress-donning African-American men like Eddie Murphy (The Nutty Professor) and Martin Lawrence (Martin).

1975 Tim Curry’s Dr. Frank-N-Furter was the ”sweet transvestite” of The Rocky Horror Picture Show, which launched a lifetime of midnight drag-alongs.

1982 Dustin Hoffman got the girl — and an Oscar nomination — by becoming Dorothy Michaels in Tootsie. Stuff that in your nylons, Tom Hanks (Bosom Buddies)!

1982 A woman pretending to be a man pretending to be a woman? Only Julie Andrews could pull it off with such grace and style in Victor/Victoria.

1990s RuPaul rose from NYC’s clubs to become a world-class drag-queen supermodel, introducing straight men everywhere to the term ”You better work!”

1994-1995 Cross-dressers went cross-country, spreading outrageous, life-affirming messages in 1994’s Aussie-set Priscilla, Queen of the Desert and 1995’s To Wong Foo…

2005-Present Oprah-approved Tyler Perry brings Madea, a gun-toting, wisdom-dispensing old woman — think Mrs. Doubtfire, only edgier — to the big screen.

2007 The movie’s director may say he’s ”not in drag,” but Travolta had best be campy in Hairspray or we’ll be aching for a return to Divine in the 1988 original and Harvey Fierstein (2002-04) on Broadway!