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23. Billy Corgan and Tila Tequila

Remember Tila Tequila? She had that MTV reality show A Shot at Love with Tila Tequila in 2007 and then she showed up at Bravo’s A-List Awards with Smashing Pumpkins frontman Billy Corgan in 2009. The romance was short-lived at best, but still one of the weirdest celeb hook-ups ever.