24. RuPaul and Milton Berle Dress Each Other Down (1993)
Few VMA pairings have been more inspired than Milton Berle and RuPaul, the most famous cross-dressers of the Forties and the Nineties, respectively, presenting a Viewer's Choice Award to Aerosmith (not for "Dude Looks Like A Lady," if you were wondering). But while it could have been comedy gold — Mr. Television himself in a three-piece suit standing at eye level with RuPaul's push-up bra — their chemistry left something to be desired. Berle, rattled by the rowdy crowd, kept telling audience members "Shut up, will ya?" and stammered "He wasn't supposed to say that!" when RuPaul adlibbed.