Rudy Giuliani's impassioned speech at the Republican National Convention has made him an ally for Donald Trump, however, this lost video shows how far the two go back.
The footage from 16 years ago has surfaced of Giuliani dressed in drag during his tenure as mayor of New York City.
He performed the skit with Donald Trump for a charity dinner where the real estate tycoon called Guiliani’s character "really beautiful."
At one point in the skit, Trump pressed his face against Giuliani's "breasts," to which the mayor responded: "Ooh, you dirty boy!"
Giuliani's character exclaimed: "Donald, I thought you were a gentleman!"
Trump then fired back: "Don’t say I didn’t try."
As shocking as it is to see Giuliani dressed as a woman, it's not the only time. He also donned a dress and wig in a 1997 skit on Saturday Night Live.