Credit: CBS

Donald Trump and Rudy Giuliani once participated in a 2000 comedy sketch that featured Giuliani in drag, video of which Stephen Colbert unearthed on Tuesday’s episode of The Late Show.

Colbert played the clip as part of a segment designed to hit back at Giuliani for his claims that Trump’s opponent for President of the United States, Democratic nominee Hillary Clinton, has an undisclosed illness. In an earlier interview with Fox News, Giuliani urged viewers to do a Google search for “Hillary Clinton illness,” a query that now leads to numerous stories about Giuliani’s claims.

“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,'” Colbert explained. “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. 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.”

But the Late Show host said he wasn’t surprised Giuliani and Trump have tried to diagnose Clinton from the sidelines, as they are “experts in the female anatomy.”

“It’s true,” Colbert said, before playing a clip from the drag sketch. In the 16-year-old video, which was produced for the Inner Circle Show, an annual event held by the media to spoof the mayor and other political figures in New York City, Giuliani is dressed as a woman and finds himself confronted by a “very forward suitor” in Trump. The current GOP nominee is shown putting his face into Giuliani’s chest.


Watch a clip of the video and Colbert’s take on the conspiracy claims about Clinton’s illness below.