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The only 2008 presidential candidate who's performed in drag. Frightening but true. Giuliani dressed in drag for the 2000 Mayor's Inner Circle Press Roast. Wearing a blond wig and a mink, Giuliani vamped it up as Marylin Monroe and Donald Trump got into the act by rubbing his head between the mayor's fake boobs.

As if the cowboy in the flight suit with the stuffed cod piece wasn't embarassing enough for America! The leading contender for the 2008 Republican nomination is on video prancing around in a makeup and a dress. America's mayor or America's sweetheart?

Rudy Giuliani isn't exactly what I'd call presidential, but if he cheats on his current wife (like he did on his last two) we don't have to worry because he can always double as his own First Lady.
by DK Sett May 07, 2007
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a 9-11 good 9-11 candidate 9-11 for 9-11 the 9-11 presidency 9-11
Rudy Giuliani won't shut up about 9-11 because the thinks that if he reminds people about one of the worst days in U.S. history.
by codeman2103 October 12, 2007
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A moderate/centrist Republican and former Democrat who served two terms as mayor of New York City in the 1990s and early 2000s; the man who turned the Big Apple around after many years of decline and decay and showed tremedous leadership ability on 9/11. Essentially a fiscal conservative, but socially liberally on issues such as abortion and gay rights. Generally well liked by moderate Republicans, moderate Democrats and Libertarians, but disliked by the far right and the far left. A man who would have a very good chance of becoming president in a general election in 2008 but who, regrettably, probably couldn't get through a GOP presidential primary because most of the GOP has been hijacked by far-right religious fundamentalist nutcases (also known as "The American Taliban").
Swing Voter #1, A Moderate Democrat: "I think Rudy Giuliani could easily carry a lot of Blue States in 2008. I wouldn't vote for a neocon whack job like Jeb Bush or Rick Santorum, but I would vote for Rudy Giuliani."

Swing Voter #2, A Libertarian: "Yeah, I like Rudy. I would probably vote for him for president in 2008. He isn't ideal from a Libertarian standpoint, but he's good. He isn't a tax-and-spend ultra-liberal, but he isn't a neocon Bible Thumper either. But do you really think Rudy could make it through a GOP presidential primary in 2008? Let's be realistic: his positions on abortion and gay rights--the very things that would play well with swing voters--would prevent him from winning a GOP presidential primary. Rudy is a moderate, and moderates are hated by the jihadists of the Christian Right. Just ask Arlen Specter."

Democratic Party Operative: "Please, dear God, don't let Rudy win the GOP presidential nomination in 2008. He would probably carry Pennsylvania, California and other Blue States. Hopefully, the GOP will behave like the self-destructive idiots that I think they are and give the nomination to some neocon wacko on the far right like Rick Santorum or Sam Brownback--someone my Democratic candidate could easily slaughter in a general election. If the GOP is smart, they will make my job much more difficult and nominate someone as electable as Rudy. But lucky for me, the GOP isn't very smart. Ha ha ha ha ha! Hey, Rudy, if the neocon Bible thumpers diss you too badly in 2008, you might want to consider becoming a Democrat again. Call me, OK??????"
by Sir Bullwhip October 09, 2006
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Despite his frequented controversy surrounding his mayoral policies, Rudy Giuliani has rightfully earned his place as one of the most signifigant political leaders of our time. He reversed a staggering and disgustingly increasing crime rate, reduced welfare dependancy, got rid of many seedy disgusting sex shops that plauged New York City, and instituded many policies and programs to better life for New Yorkers in all 5 buroughs. It it wasn't for the leadership displayed by Rudy Giuliani, then New York City would be nothing more than a disgusting crime plauged gangster's paradise, instead of the pearl of the civilized world such as it is today!
Rudy Giuliani is one of the greatest political figures of our time.
by preppyguy21 August 29, 2004
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