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10 Most Disturbing Cross-dressing Performances Of All Time

3 August 2008 6 Comments

How are we men supposed to Return To Manliness when some our best role models decide to dress in drag? Either for charity, on a dare, for Halloween or their jobs – cross-dressing is killing our vision of what these manly men are all about. Nevertheless, it has been done, and quite frankly, done successfully (as far as I can tell).

The idea was formed watching, yet again, the incredible movie Birdcage. When the directors of the movie were able to get Gene Hackman, one of the manliest of men, to dress up as a woman, the topic gained momentum.

The criteria: 1) Men who have exhibited manliness and considered manly in their profession; 2) it was for a job, event or promotion – not just because; and 3) the act had to receive notoriety. Finally, under no circumstance, shall any cross-dressing by a man be tolerated unless done for comedic relief.

On to the disturbing performances…

Dustin Hoffman in Tootsie set the standard for men dressing up in drag. Dustin Hoffman is truly one of the great actors of our time and has many traits that exhibit manliness. He just went off course in this flick. He poses as a woman to get work (not too bad) and then falls in love with another woman actress. He has to keep up the charade, though, to hold his job as he is courting Jessica Lang’s character, the female star of the show. Of course, the realistic story of two older guys past their prime falling in love with Hoffman’s drag character makes this performance the classic that it is.

Robin Williams in Mrs. Doubtfire is yet another classic performance. Robin Williams, similar to real life, will do just about anything for his kids. As an out of work Dad, his wife (played by Sally Fields) kicks him to the curb and he can no longer dote on his children. To stay close to them, he applies for the nanny job as Mrs. Doubtfire and is probably the best nanny ever! Great flick…

Jamie Farr as Maxwell Klinger in M*A*S*H was a curious choice. He wasn’t always playing a cross-dressing nutjob looking to get out of the Army through a Section 8 (mentally instable). Sometimes his character was just Maxwell Klinger, the fun loving corporal that eventually gives up his cross-dressing ways to get promoted to sergeant. He has to be included, though, since he was a big part of the INCREDIBLE success of this show.

Nathan Lane and Gene Hackman in Birdcage are as disturbing as it gets for this list. Nathan Lane is a natural at the cross-dressing thing and gives one of the best performances in drag – ever. But Hackman is all about manliness. He is brilliant in so many films and is such a legend; you never thought they could get him to do it. But there he was in all his cross-dressing glory for about 5 minutes on film. That was enough to make the list.

Tom Hanks and Peter Scolari in Bosom Buddies. The show was on for only 2 seasons and would never have made the list if not for a young Tom Hanks. Is there a better depiction of a modern day man fighting through adversity than his role in Castaway? He depicted true will to live, tenacity, intelligence, emotional stability and insatiability – guy had it all. Bosom Buddies was very funny and deserves a nod.

John Travolta in Hairspray. This was not John Travolta pre-Pulp Fiction. It was Travolta after resurrectinghis career as one of the true manly actors of our time. He has played in tons of roles that depict modern manliness well. For him to strap on the brazier and makeup to play this role in Hairspray, I am still trying to sort this out in my brain.

Patrick Swayze, Wesley Snipes, and John Leguizamo in To Wong Fu. All fantastic actors and have played great manly parts in their day. The performances in this movie were so dragqueen real, I needed to turn it off after 10 minutes (the third time I saw it). Seriously, Lequizamo as Chi-Chi Rodriguez was way too real with the snapping of the fingers and true drag queen attitude.

The Wayans brothers in Whitechicks. The comedy doesn’t always sit right with a lot of people, but these are very good comedians. Their show In Living Color dominated the airwaves for a few years and was cutting edge. What put this performance on the list was the awe-inspiring makeup. I keep looking at the characters and trying to envision the Wayans, but simply can not. It may have been one big spoof and they weren’t really performing in drag at all.

Sorority Boys. Barry Watson, Michael Rosenbaum and Harland Williams play raunchy and stupid in this movie. It was a stretch to put them in the list since it was always very clear they were doing it for one reason, but nevertheless a good comedy. You have to be into this type of comedy, though, for it to make any sense.

Rudy Guiliani as himself. At a political roast 10 years ago, he appeared in drag and shocked New Yorkers (that alone put him on the list). The video was replayed a billion times when he ran for president earlier this year. The tough talking, extremely successful mayor did it for comedy and for fun and that gave him the nod. He then went on to do it again on SNL later that year. That pushed it from funny to pretty freaking weird.

You might be thinking “Where’s Dennis Rodman?” or “How about Jaye Davidson in The Crying Game?” Both of these cross-dressing exhibitions are classic and timeless. Plenty of notoriety and all kinds of disturbing. Problem with both of these are that they are a little too disturbing. Dennis Rodman dressed in drag too many times to be funny anymore and Jaye Davidson had nothing to do with comedy. Also, he was little too real to consider.


  • Hayden Tompkins said:

    Ugh, “Silence of the Lambs”. :shudder: That one gave me nightmares.

    Hayden Tompkinss last blog post..How To Be a Better Mom

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  • Virilitas said:

    Do you remember Martin Lawrence as “Sheneneh?” Ha ha ha.

  • Barry @ Cross Dressing said:

    It is good to know that such macho media men can look so good and convincing as women
    .-= Barry @ Cross Dressing ´s last blog ..How does Malvolio wearing cross gartered yellow stockings relate to cross-dressing? =-.

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