A 1985 installment of The Fall Guy had both guest star Scott Baio and regular actor Douglas Barr transformed into females in order to protect a witness they were watching. Shown with them is series regular Heather Thomas (who had costarred with Baio two years prior in the telekinesis comedy Zapped!)
In the 1969 drama The Damned, Helmut Berger kicked things off with a Marlene Dietrich impersonation.
Later in the film, a gaggle of drunken, half-naked, cross-dressed young Nazis are slaughtered in a depiction of the infamous “Night of the Long Knives” incident.
The normally urbane and elegant George Sanders played a transvestite piano player in 1972's The Kremlin Letter.
Gene Hackman made a rather shocking appearance as a bleach blonde at the climax of 1996's The Birdcage. Seeing this for the first time, I thought JoAnn Castle of The Lawrence Welk show was making a cameo in the movie!
We close with a couple of non-film or TV instances of drag. These two lovely birds are serious British actors Laurence Olivier and Kenneth More, all done up in their finery for a 1960 charity event at The London Palladium!
The man in the middle, of course, is swashbuckling superstar Errol Flynn. His two satin-covered cuties are none other than he-man Robert Mitchum (on the left) and gymnastically-inclined adventure star-turned-serious-actor Burt Lancaster! Fascinating picture... I apologize for the random, scattershot arrangement of some of these photos, but such is often the way when I approach these sorts of collections.
Finally, just for the shits and giggles of it, I give you a hysterical shot of yours truly. You see, even I, in a weak moment, once got my girl on for Halloween. This was about 1999, I think, and I was the life of the party, my darlings! Frankly, if I could be so bold, I think I look better than a lot of the stars featured in this post and I was strictly amateur, believe me. :-)