Stephen Colbert shared an old video of Rudy Giuliani and Donald Trump that was produced for the 2000 Inner Circle Show

By Lindsay Kimble
August 24, 2016 03:45 PM

The fight to the White House is starting to look a little more like a drag race.

While prodding around on the Internet under Rudy Giuliani‘s orders to Google "Hillary Clinton illness," The Late Show host Stephen Colbert unearthed an old video sketch that featured Donald Trump motorboating the former New York City mayor – 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 flirting with Giuliani as he wore a wig and dress.

“You know, you’re really beautiful,” Trump said to Giuliani 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 Republican candidate.

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

Of his findings, Colbert said on Tuesday, “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.’ ”

Colbert also addressed Giuliani’s claims that Clinton, the Democratic candidate for president, is hiding an undisclosed illness – something he asserted again during a Fox News appearance on Sunday.

“[I want to] point out several signs of illness by her, all you have to do is go online,” Giuliani said. In response, Clinton’s campaign has called Giuliani’s claims “deranged conspiracy theories,” according to Politico.

Joked Colbert, “I took Giuliani at his word. I Googled ‘Hillary Clinton illness,’ and this is true, the very first result is: ‘Giuliani fuels Clinton health rumors again and again.’ ”

“Here’s what’s happening. Giuliani says, ‘She’s not healthy, and look it up on the Internet.’ And when you look it up on the Internet, it says that Giuliani says she’s not healthy and to look it up on the Internet,” Colbert continued. “It’s an endless loop. It’s like a snake with its tail in its mouth. Or a man with his head up his own ass.”