"Weird Al" Yankovic
Three Wins: Best Comedy Recording (1985), Best Concept Music Video (1989), Best Comedy Album (2004)
It was surrealistic the first time [I was nominated]. I was just a couple years out of college — with a degree in architecture, no less — and all of a sudden, there I was in a rented tux at the Grammy awards! And I have to say, as mind-blowing as it was 30 years ago, it doesn't feel any less mind-blowing now. Being a Grammy nominee never gets old — I'm not jaded about it in the slightest.
The very first time I was nominated, I was up against Rodney Dangerfield and Richard Pryor, so, no, I wasn't expecting to win. When they called my name, I thought somebody had made a mistake!
[In 2007] I remember Chamillionaire came up to me on the red carpet to tell me that "White & Nerdy" clinched his Grammy win because my parody made it "undeniable" that "Ridin'" was the Rap Song of the Year.
[All of the ceremonies I've attended have] all been great and memorable, but my favorite was probably last time — three years ago — because I got to bring my 8-year-old daughter with me to the Grammys. She even got interviewed on the red carpet, and totally nailed it!