For the tenth annual MTV Video Music Awards, which aired live on September 2, 1993, somebody came up with the idea of having veteran comedian Milton Berle present an award with RuPaul. By RuPaul’s own admission, the pairing made sense on paper, given Berle’s long history of dressing in drag. However, according to the Drag Race star’s 1995 memoir Lettin’ It All Hang Out, things got off to a rocky start between the two because Berle reportedly got a little handsy during their rehearsal, and allegedly grabbed RuPaul’s fake breasts as soon as they met.That awkwardness pretty obviously carried over onto the stage, with Berle introducing himself and RuPaul as “Wilt and Milt,” and repeatedly making faces at RuPaul’s chest, which happened to be at eye level for him. At first, the jabs seem lighthearted and clearly scripted, like when Berle tells RuPaul, “I love that gown,” and RuPaul responds by saying, “You should, queen, it’s one of your old ones.” After Berle jokes that he wishes he’d said that, RuPaul fires back with, “Don’t worry, you will”—a nod to Berle’s reputation for stealing material. The 1993 MTV VMA Moment When RuPaul and Milton Berle Stopped Playing NiceFrom there, Berle quips that he’s beginning to feel like a “straight man,” playing with the double meaning of the term (for those who don’t know, the straight man in a comedy duo traditionally served as the foil to the person who got all the laughs). “I don’t know about him, but me,” Berle clarifies, gesturing toward RuPaul in the process. RuPaul looked visibly uncomfortable by that point, and that’s when the ad-libbing evidently began. “40 years ago, when I was on TV, I used to wear gowns myself,” Berle explains. “Is that right? You used to wear gowns, and, that’s funny, now you wear diapers,” RuPaul replies, earning a mixed reaction from the audience. Berle then makes it clear to the crowd that the last line wasn’t on the teleprompter. “You wanna ad-lib? I’ll check my brains, we’ll start even,” says Berle, before making RuPaul redo the planned dialogue, which ends with him revealing that he’d stopped wearing women’s clothes because it was a drag.You can check out their full exchange in the video above.The post RuPaul and Milton Berle Had One of the Most Awkward MTV VMA Moments Ever appeared first on VICE.