Donald Trump once stuck his face into Rudy Giuliani’s chest for a drag-queen comedy skit — and the video refuses to die

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Inside Edition / YouTube

  • The US President once pretended to sexually harass his now-lawyer in a comedy skit recorded in 2000.
  • Footage shows Trump, then a celebrity businessman, and Rudy Giuliani, then New York’s mayor, engaging in a bizarre drag encounter.
  • The footage was made for a joke – but keeps re-emerging as the pair’s fortunes remain intertwined.
  • Millions of people have seen the video on YouTube. It also trends routinely and has been dredged up for late-night TV.
  • Giuliani’s latest gig is trying to downplay the Stormy Daniels scandal as part of Trump’s legal team.

President Donald Trump once thrust his face into the ample chest of his now-lawyer Rudy Giuliani for a drag-queen-themed comedy sketch – and the video refuses to die.

Footage recorded in 2000, when Giuliani was mayor of New York City and Trump was a celebrity businessman, shows the surreal moment.

It came about as part of the Mayor’s Inner Circle Press roast, a parody event in which New York mayors show their light-hearted side.

The set-up features Giuliani’s alter-ego splashing perfume on “her” neck and then bosom in an attempt to charm Trump, who then goes further than expected and sticks his face into Giuliani’s chest.

Giuliani reacts by calling Trump a “dirty boy” and slapping him. As Giuliani walks away, Trump looks at the camera and says “Well, you can’t say I didn’t try.”

Giuliani, or

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Giuliani, or “Rudia”, making a shocked face after the Trump encounter.
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YouTube/itsgiulianitime

The skit takes on an uncomfortable sheen in light of later sexual allegations against Trump, and the infamous “grab them by the p—-” Access Hollywood tape.

Giuliani made a splash several times dressing as “Rudia” – his drag alter-ego – for the event. (A 1997 report from The New York Times of Rudia’s first outing described the spectators as “thunderstruck.”)

The skit was good for a few laughs at the turn of the 20th century. But now it reappears routinely to baffle the internet as the lives of its two protagonists take stranger and stranger turns.

Trump's reaction to being slapped.

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Trump’s reaction to being slapped.
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YouTube/itsgiulianitime

As of Monday, a re-post of the video was one of the top items in reddit’s thread for gifs and videos.

A version hosted on YouTube since 2006 has 2 million views and counting. Around a dozen other versions also exist with more modest totals.

It previously made an appearance during the 2016 presidential campaign, when Stephen Colbert ran it on his show in light of an attack by Giuliani, then a Trump campaigner, on Hillary Clinton.

When they recorded the hammy scene, Trump could have had no idea he would one day be President of the United States.

Giuliani and Trump (then President-Elect) together in late 2016.

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Giuliani and Trump (then President-Elect) together in late 2016.
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Drew Angerer/Getty Images

Giuliani would likewise have had had no inkling that his future job would be trying to shut down a scandal surrounding the exact mechanism by which the President gave $130,000 to a porn star to stop her talking about the time they allegedly had sex.

Though he set out to defend the president from allegations of wrongdoing, Giuliani’s attempts have thus far backfired. He told Fox News’ Sean Hannity that Trump “reimbursed” his lawyer for the payment to Stormy Daniels, the porn star, “over a period of several months” – something that Trump had previously denied doing.

The result of his interventions has been intensified media scrutiny of Trump, during which Giuliani potentially opened the floodgates to even more trouble.

In response, Trump has publicly distanced himself from Giuliani, and is reportedly going sour on him in private, too.