Rupaul vs. Milton Berle
At the 1993 MTV VMAs, drag superstar RuPaul and late comedy legend Milton Berle caused quite scene, when backstage tensions between the two spilled over onstage as they presented an award together. Berle famously fondled Ru’s fake breasts, prompting the drag star to spitefully poke fun at Berle’s past comedic cross-dressing moments, “So you used to wear gowns, but now you’re wearing diapers.” Berle fired back, “Oh, we’re going to ad lib? I’ll check my brain and we’ll start even,” making the moment even more awkward and leaving audience members stunned by the scene.