This Whole Thing is Just a Drag...

Actors have been donning women's clothes since the time of Shakespeare (at least!), though in those instances it was in order to portray female characters. Since it became acceptable for females to act upon the stage, that practice was no longer necessary, yet now and again there has been either a reason or a desire to get the guys in drag again. Today, we'll look at a selection of famous men who dolled up as a female be it for a role (as in most cases) or for fun. This isn't meant to be a history lesson, just a sashay through pictures I've collected, so apologies to anyone who is left out!

One of the most successful stage plays having to do with drag was the enduring Charley's Aunt, which, in 1892, broke all records in London and lasted (across two venues) until 1896. The play was then mounted on Broadway where it ran another four years, a stunning success. There was a 1915 silent film version and then a 1925 remake (remakes are nothing new in the film business!) The latter starred Sydney Chaplin (Charlie's brother) and he is shown here as the hapless manservent coerced into portraying the title figure.

Years later, this story was musicalized (and tweaked) into the 1948 Broadway hit Where's Charley?, starring Ray Bolger (a talented song and dance man and the Scarecrow of 1939's The Wizard of Oz.) In 1952, a color film version was made starring Bolger as well. Bolger returned to the property more than once, creating a longstanding association between himself and the material (not to mention the famous song from the score, “Once in Love with Amy.”)

Other old-time comedians who found themselves on the other side of a curly wig and skirts included Gus Schilling and Joe E. Brown, who are shown here in 1943's Chatterbox with Judy Canova. The men were taking turns playing Brown's mother for Canova's benefit until they both made the transformation at the same time! Incidentally, Canova's daughter Diana, became a popular 1970s actress in her own right, with Soap amongst her credits.

In 1944, the famed comedy duo Abbott and Costello put forth the movie Lost in a Harem and the screwball plot had Lou Costello flouncing around in drag impersonating a sultan's wife (with Bud Abbott impersonating the sultan until he's found out by the real McCoy, played by Douglas Dumbrille.) I do like all the bric-a-brac on the men's turbans below and think Joan Crawford would probably have turned said items in a necklace (both of them into one, in fact!) had she come upon them in the mid-'60s!

This was far from the only time that Costello got into a skirt. He did so in several movies or at other events. Here, the duo is shown again, this time in a western setting, with Lou in petticoats.

It's a longstanding tradition for comics to slither into a dress for humorous effect. Let's take a peek at some of the more well-known examples. We'll start with Uncle Miltie, Milton Berle, who incorporated drag into his act throughout his long career. This shot is late in the game (circa 1987) with Miss Phyllis Diller (God rest her.)

He's shown here with Mr. Bob Hope during a TV special. Those of my generation will recall Berle appearing as himself and as himself in drag for the music video of Ratt's “Round and Round!” What a surprise match-up that was.

Hope was known to suit up on occasion as well. Here, he's shown in a 1981 special, along with Olympian Bruce Jenner and football-player-turned-actor Merlin Olson, in a comic spoof on The Mandrell Sisters (calling themselves The Mandrake Sisters.)

Jonathan Winters trucked out his concoction, Granny, on many an occasion.

(Incidentally, Granny seems to be the inspiration for Alan Hale's characterization in this fantasy sequence from Gilligan's Island.)

Flip Wilson, a highly-popular comedian and variety show host of the '70s, brought the world the vivacious, confident and sharp-tongued Geraldine (shown here giving Joe Namath a steam bath.)

Geraldine was quite a hit and even had her own recordings!

Of course, no fan of M*A*S*H could forget the ever-present Jamie Farr, continually dressed in drag as a way of (unsuccessfully) trying to get out of the service.

During his Saturday Night Live days in the mid-to-late '80s, Dana Carvey scored a huge hit with his creation, The Church Lady, a snarky, pious chat show host who would often utter (with a thick layer of sarcasm), "Well, isn't that special...?"

Now to examine some more obscure instances, comedian Joey Bishop looks none to pleased to be sporting this wig, female suit and makeup.

Two Dons donned frocks on TV in 1964. Don Wilson dolled up for an episode of The Jack Benny Show while Don Knotts (as Deputy Barney Fife) was undercover as a cleaning woman in order to snag a bad guy in The Andy Griffith Show.

Knotts got girly again for a 1970 Jim Nabors special, shown with longtime pal Griffith.

For the 1967 James Coburn film The President's Analyst, Godfrey Cambridge appeared in drag, looking something like Fred Sanford's (of Sanford and Son) Aunt Esther's little sister!

Impressionist Rich Little donned a blonde wig in order to do a number opposite Debbie Reynolds (from, I believe, a 1972 episode of The ABC Comedy Hour?)

Sonny Bono, during The Sonny and Cher Comedy Hour days, also got into the act, not an easy feat when you're sporting a thick mustache!

TV sitcoms, as already touched on above with Gilligan's Island and M*A*S*H, frequently turned to actors in drag for a laugh. One episode of the 1960s series That Girl, which starred Marlo Thomas, had her boyfriend Ted Bessell trussed up and turned out as a blonde.

Note the hairy legs under the hose in this shot!

The 1968 show The Ugliest Girl in Town had star Peter Kastner in drag much of the time as he was disguised as a female model (!) in order to be close to the English starlet he's in love with. To me, the poor guy looks like Johnny Carson in a wig more than anything!

The 1970s anthology sitcom Love, American Style occasionally put a guest actor through his drag paces. Here, cigar-chomping Warren Berlinger has a scene with Joan Van Ark.

Next is Michael Callan cozying up to Beth Brickell while undercover at a women's lib meeting.

Fans of Happy Days probably recall the early episode that had Ron Howard forced to dress up as a girl as part of a hazing ritual and winding up dancing with the always-womanizing Fonzie (Henry Winkler.)

The 1980s sitcom Bosom Buddies is another show that centered on its male stars having to keep up appearances as women. This was at the dawn of Tom Hanks' career as he costarred for two seasons with Peter Scolari.

Looking uncannily similar to the gents above are Bob Saget and Dave Coulier in an episode of Full House.

It's not always been the comedies that feature a man in drag. For a 1976 episode of Police Woman, John David Carson played a cross-dresser. His character's name was Tommy Shaw, but the alter-ego's name was Charlese Parker.

Famed female celebrity impersonator Charles Pierce made a bizarre appearance in a 1978 episode of The New Adventures of Wonder Woman. (His voice was dubbed by a female in the episode.)

He played a high-priced espionage agent sent to steal information from Lyle Waggoner and felt the need to do so while disguised as a woman. If you were Waggoner, would you not raise an eyebrow or two at an Army officer who looked like this?!

One T.J. Hooker episode concerned a deranged nurse who is killing other nurses (after first sending them flowers.)

The nurse turns out to be a male doctor in drag who suffers from issues stemming from his mother's mental abuse.

In a truly sad and somewhat ironic turn of events, barely a year after this 1984 episode, the actor David Huffman, who'd led a very busy, promising career as an actor to that point, was himself killed by stabbing. He chased a teen thief (and illegal immigrant) into a canyon who then turned on him with a screwdriver, stabbing him to death. Huffman was thirty-nine.

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!)

Occasionally, Scott Bakula would find himself stuck in the body of a female during the course of the late-'80s/early-'90s fantasy series Quantum Leap. Each week, his character inhabited the body of someone else from the past, present or future. In this instance, a well-dressed lady.

In 1998, a famous, but not as busy as now, RuPaul guest-starred on Chuck Norris' action series Walker, Texas Ranger, dwarfing both Norris and costar Clarence Gilyard.

In recent years, RuPaul has emerged as one of the all-time most visible drag queens as far as the mainstream arena is concerned, thanks to RuPauls' Drag Race, Drag U and song, music videos, etc...

When it comes to the movies, few cross-dressing actors are as memorable as Jack Lemmon and Tony Curtis in Some Like it Hot (1959.)

Here, William Holden, during a visit to the set, gives Tony Curtis the once-over.

These gentlemen, as I noted above, were far from the first, though. Just among the better known. A few years earlier in 1952, The Bowery Boys dressed as women for a sequence in the college-set comedy Hold That Line. The real draw in this picture, though, is the dreamy John Bromfield, one very handsome man. (You can read more about Mr. Bromfield – as well as see more of his yummy physique - here.)

In 1949, Cary Grant barely seemed to alter his visage at all beyond a wig when he starred in I Was a Male War Bride.

Also in 1949, Alec Guinness portrayed all members of one family in Kind Hearts and Coronets. Here, we see him as one of the ladies.

A decade later, Peter Sellers played three roles, one of them a queen, in The Mouse that Roared. This tradition has been carried on in more recent years by Eddie Murphy and Tyler Perry (and thanks to advancements in prosthetics and technology, more believably, though ol' stick in the mud me appreciates when things were done the hard way.)

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.

John Hansen made his cinematic debut in the 1970 film The Christine Jorgensen Story, playing the first ever transsexual. The campy, heavily-derided movie practically ended his career at the start, though he managed to eke out about a decade of spotty work. One of the big criticisms of this movie was the fact that Hansen looked prettier as George Jorgensen than he did as the female Christine!

The normally urbane and elegant George Sanders played a transvestite piano player in 1972's The Kremlin Letter.

In 1974, Alan Arkin and James Caan starred in the action-heavy buddy comedy Freebie and the Bean and went up against a transvestite hit man played by Christopher Morley (shown here in the midst of a dress-ripping fight scene!)

Few people who ever saw Divine in a movie were likely to forget it. Here, the portly superstar poses with Tab Hunter in 1981's Polyester.

Tab returned to costar with Divine again (along with Lainie Kazan, on the right) for 1985's Lust in the Dust.

Divine starred in Hairspray in 1988, which was later turned into a Broadway musical that starred Harvey Fierstein (shown here during a holiday parade which featured an excerpt from the show.) Later, the musical was filmed as well with John Travolta, but the less said about that performance the better.

Speaking of parades, I'm not sure where little Gary Coleman might have been when this shot was taken, but it could have been during some sort of celebration!

Dabney Coleman put on a wig, hat and dress for one of his movies (I'm afraid I don't know which!)

Another highly-recognizable, iconic man-in-drag personage is that of Dustin Hoffman in Tootsie (1982.)

An unlikely drag personage came along in the 1989 buddy flick Tango & Cash, starring Sylvester Stallone and Kurt Russell. At one point, in a bid to sneak Russell out of a nightclub while in the company of Stallone's little sister Teri Hatcher, Russell is painted up and bewigged to resemble a lady.

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!  

Our celebrity final photo is one that I found to be interesting on several levels. For one thing, for whatever reason, I don't tend to think of these three stars together all at once. For another, the two stars in drag are not ones that I would ever think of as appearing that way. This was for some sort of charity event or part, I believe. Do you recognize them? If you wish to guess, then wait a moment to scroll further.

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. :-)