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"The checkerboard Vans with the floral print seemed to be appropriately grotesque" to enhance his already wacky image, Yankovic says. Today he has 100 or so pairs, and he's sported them on album covers, in music videos, and onstage. He wears them even when he's not performing. "They're sort of like the comfort food of shoes for me," he says.

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Last updated April 30 2009: 10:47 AM ET
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