The Hon. Rudolph Giuliani, in Drag, on the cover of The National Review:

[elehhhhna]

[babylonsister]

1. Bwhahahaha! nt

[Joanne98]

2. OMG! Is that really him?

[DoYouEverWonder]

3. Yep,

I think it was for a Halloween Party or something back when he was mayor.

[Skidmore]

5. He's got Betty Davis eyes...

[NYCGirl]

6. Here's a video:

http://www.youtube.com/watch?v=4IrE6FMpai8

It was from the Mayor's Press Roast — and he was in drag a few times.

[DoYouEverWonder]

7. Thanks for the link

I hadn't seen that one before. I'd only seen some of the pics.

The really funny part is that Rudy actually looked good has a transvestite. You get the feeling he may have done this on a fairly regular basis?

Rudy is one strange dude.

[AndreaCG]

12. You're kidding right?

He is ugly as sin. If you want to see some passable transvestites check out the ads in the back of the Village Voice (probably other weekly papers too). There are some you could swear were women.

[kskiska]

13. Here's another

[Joanne98]

11. NOOOOOOOOOOO!!!!!!!!!!

So those rumors about him being a cross-dresser are true.

[WCGreen]

4. Well Hello Rudy...

Yes Hello, Rudy

It's so nice to see you back where you belong...

You're lookin' swell, Rudy...

I can tell, Rudy...

You're still glowing, your sill growin' your still...

Goin' strong....

[UTUSN]

8. A kinder and gentler Fascist to follow Shrub n/t

[aint_no_life_nowhere]

10. Actually, George Bush himself used to dress in drag in high school

Photo from the New York Times, showing George and his fellow cheerleaders at Andover, dressed in female cheerleader clothes:



Earning A's In People Skills At Andover

by Nicholas D. Kristof

Perhaps there have been other presidential candidates who have dressed in drag, flaunting their legs from beneath a (fairly short) white skirt. But George W. Bush is probably the only one who has done it in front of a camera.

A photograph showing George and friends wearing wigs and employing falsies to fill out their sweaters appears in a yellowed copy of the school newspaper of Phillips Academy here in Andover, near Boston. It was 1963, and George, then a high school senior and head cheerleader, was leading a skit intended to mock rival schools.

(...)

http://partners.nytimes.com/library/politics/camp/061000wh-bush.html

[JohnnyLib]

9. Reminds me

of Cabaret, especially in the current political climate