Giuliani's Cross-Dressing Antics Debated

New York Mayor Rudolph Giuliani, right, dressed in drag as a role in "Victor/Victoria," sings with Julie Andrews at the New York Hilton in this March 1, 1997 file photo, during an event presented by the Inner Circle. Shocking New Yorkers is difficult, yet Giuliani teetered close to the line when he sauntered on stage wearing a platinum blond wig, a face full of makeup, dainty white gloves and a frilly pink gown filled out in all the right places. Dressing in drag is de rigeuer for New York mayors at the city's annual Inner Circle dinner - but how it will play with conservative voters in the Republican presidential primaries is unknown. (AP Photo/Joe DeMaria, File) (Joe Demaria - AP)

Southern Baptist Convention official Richard Land said gay issues represent just one area of the problems religious conservatives have with Giuliani.

"There are so many dealbreakers for Giuliani, it's difficult to know where to start," he said.

Throughout his eight years in City Hall, Giuliani supported laws that protected gays against harassment, marched in gay pride parades, welcomed the Olympic-style Gay Games to New York City and, after his second marriage broke up, lived with two friends who happened to be a gay couple.

He does not support gay marriage, but he does not see the need to ban it with a constitutional amendment. And in a 1994 cover story with The Advocate, a national gay magazine, he condemned Pat Buchanan's speech at the Republican National Convention two years earlier during which the failed presidential candidate declared a "cultural war" against homosexuality, radical feminists, abortion rights supporters and other "liberals."

The speech, Giuliani said, "tried to narrow rather than to broaden the Republican Party. There is no reason why the party shouldn't appeal to gays and lesbians in the same way it does to all Americans."

Over the years, Giuliani's relationship with gays has not been exactly cozy _ he was often heckled while marching in the city's annual gay pride parade.

Asked this month about his theatrical past, Giuliani told Fox News that it shows voters another side of him.

"I think what they'll find out about me is I enjoy having fun. I mean, I really enjoy those Inner Circles. I made them fun, and I enjoyed them," he said. "And so you're going to get a couple of things people can interpret different ways, I guess."