Well, to be fair, like a woman. He has dressed in drag numerous times in skits, including on national television for "Saturday Night Live. Of course, I don't have a problem with this. Even though the last guy who did this on a consistent basis and worked for the government was J. Edgar Hoover -- and that didn't work out so well for us.
The Full Rudy: The Man, the Mayor, the Myth | The Nation
Pim Fortuyn, you may recall, was the gay, flamboyant sociology professor turned "right-wing" Dutch politician who took a hard-line position against immigration and Islamic extremism -- two issues inextricably linked in a country where whole communities have become enclaves of Sharia law. Fortuyn was labeled as right wing by identity-politics leftists for his unapologetic view that the Netherlands should stay both liberal and libertine. His basic view was that the Netherlands has a culture too, and there's no shame in defending civil liberties, free expression and tolerance against their opponents, even if those opponents exploit liberal guilt by casting themselves as victims. In other words, Fortuyn wanted to keep the party going, and that meant taking a strong line against the killjoys. That Fortuyn could be both libertarian and tough-minded caused great cognitive dissonance in the media and on the left -- there and here.
Rudy Giuliani, what the hell is this about? You are the GOP's gay roommate-having Opera-loving cross-dressing Manhattan dandy, and now you are against the gay marriage? Back when Rudy was actually running for president hah as a Republican, we had a lot of fun with his divorces and wife-cheating-on and the fact that really the only thing he had in common with the modern Republican party was that he is a psychotic White man who wants to make permanent war on various brown people. Well, they nominated John McCain, so joke's on us, but for some fucking reason Rudy is still pretending to try to make himself palatable to 'mainstream' Republicans or something, which is why today he is against The Gay Marriage.
And, in the movie's most famous moment, caught Trump's lawyer, Rudy Giuliani, in a very compromising position. But, in the movie, she portrayed the character of Borat's fifteen-year-old daughter, who he was trying to "marry off. He then ran away I only later realized it must have been Sacha Baron Cohen.