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Try not to cringe as Trump motorboats Rudy Giuliani in drag

'You can't say I didn't try.'


Austin Powell


Posted on Oct 17, 2016   Updated on May 25, 2021, 7:04 pm CDT

In a skit that wasn’t funny then and is even less so in light of recent accusations, Rudy Giuliani once dressed up in drag and let Donald Trump motorboat his fake breasts. 

Jezebel unearthed this incredibly bizarre clip, which was filmed for the 2000 Mayor’s Inner Circle, an annual fundraiser. It features then-NYC Mayor Rudy Giuliani as “Rudia”—a character he actually used more than once—getting hit on by Trump in a department store. It ends prophetically, with Trump boasting, “You can’t say I didn’t try.”

Here’s how Daily News reported on the video at the time: 

Some guests visibly squirmed as Giuliani, dressed in drag as the Marilyn Monroe-like “Rudia” that he first played in the 1997 show, encountered Trump at a department-store perfume counter and tested the products. The tycoon sniffed Rudia’s neck, then plunged his face into her bosom, at which point the mayor shoved Trump away.

More than 10 women have accused Trump of sexual assault after a 2005 hot mic recording of the presidential candidate making degrading remarks about women was released on Oct. 7. The Daily Dot is maintaining a running list of all the accusations here

H/T Jezebel

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*First Published: Oct 17, 2016, 3:38 pm CDT