Donald Trump & Rudy Giuliani: GOP Nom Kisses Breasts Of Former Mayor In Drag — Watch

We knew Donald Trump and Rudy Giuliani were close, but we didn’t know they were THIS close! The pair starred in a 2000 comedy sketch that featured Rudy in drag, and Trump getting a little too fresh with him. Click through to watch the very uncomfortable clip!

Bless (or curse?) Stephen Colbert for unearthing this 16-year-old clip on the August 23 episode The Late Show. Rudy Giuliani and GOP nominee Donald Trump play a woman and her “very forward suitor,” and it’s weirder than you could ever imagine!

Rudy and Trump produced a short sketch for the Inner Circle Show, an annual event held in New York City to poke fun at the mayor (at that time Rudy), and other major political figures in the city. In the clip, Rudy is wearing a massive purple silk dress, a terrible blonde wig, and lipstick. It almost works.

Trump sees her walking toward him down the aisle in a department store, and stops to say, “You’re really beautiful. A woman like that has to have her own scent.” Putting on a falsetto, she asks Trump to tell him what he thinks of a perfume, that she sprays all over her chest. Trump leans in and rubs his face all over Rudy’s “breasts” and gets slapped. “Well, you can’t say I didn’t try,” Trump says before the short, weird sketch ends. It may have been funny at the time, albeit a little awkward, but given the gross sexist behavior that’s come out in recent months from Trump, it doesn’t sit very well.

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Stephen decided to drag this one out of the Internet’s archives because, well, Rudy started it! The Late Show host dedicated a segment to Rudy’s claims that Hillary Clinton‘s suffering from an undisclosed illness that will make her unfit for the presidency. Stephen said he wasn’t surprised that Rudy and the presidential candidate were commenting on Hillary’s health, since they’re already “experts in female anatomy.” Cue the video! He said that instead of googling “Hillary Clinton illness.” like Rudy has repeatedly urged, “Just go online and put down ‘Donald Trump Rudy Giuliani drag queen motorboat.’” Done!

HollywoodLifers, were you grossed out by this throwback video? Tell us in the comments!