Unearthed Sketch Features Donald Trump Flirting with a Drag-Dressed Rudy Giuliani in 2000

"Oh you dirty boy," Rudy Giuliani told Donald Trump


A decades-old video featuring President Donald Trump’s personal lawyer Rudy Giuliani has resurfaced amid Trump’s impeachment inquiry and questions surrounding the former New York City mayor’s level of involvement.

The clip was first brought back into the public eye in 2016, when Stephen Colbert — who was prodding around on the internet under Giuliani’s orders to Google “Hillary Clinton illness” — unearthed an old video sketch that featured Trump motor-boating the Republican, who was dressed in drag.

The skit — which was recorded for 2000’s Inner Circle Show, an annual event put on by media to poke fun at the N.Y.C. mayor and other local political figures — included Trump pretending to flirt with Giuliani as he wore a wig and dress.

“You know, you’re really beautiful,” Trump, now 73, said to Giuliani, 75, as he tried on perfume at a department store counter. After Trump got closer to smell Giuliani’s neck, the then-mayor sprayed a scent on his chest area. Trump went in for a whiff, pushing his face in between Giuliani’s fake breasts.

“Oh you dirty boy,” Giuliani reacted, slapping the now president.

Trump retorted, “Can’t say I didn’t try!”

Of his findings, Colbert said at the time, “Obviously that’s shocking. You’re going to want to verify that video. Just go online and put down ‘Donald Trump Rudy Giuliani drag queen motorboat.’ ”

Though Colbert’s segment was three years ago, the video has gained momentum on social media after House Speaker Nancy Pelosi announced last week that the House would launch a formal impeachment inquiry against Trump amid a whistleblower complaint that he pressured Ukraine’s government to investigate unsubstantiated theories regarding former Vice President Joe Biden, who is challenging him in the 2020 election. (Trump has denied wrongdoing).

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Giuliani, meanwhile, has been in the thick of the scandal. According to the whistleblower, Giuliani was a “central figure in [Trump’s] effort,” and had been dispatched by Trump to pressure Ukrainian officials into digging up dirt on Biden and his son Hunter, the New York Times reports.

The complaint claimed that multiple officials with the State Department were “deeply concerned” by Giuliani’s actions in engaging with Ukrainian officials.

Giuliani was subpoenaed by House Democrats on Monday for documents “related to his interactions with Ukrainian officials,” according to the Associated Press.

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