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Oh yeah, I think my sister won backstage passes to a Backstreet Boys concert through one of those "be the 6th caller" contests XD

There's a couple music things I've won, like the concerto competition my sophomore year of my undergrad. I won a free bagel once from a bagel shop by guessing their trivia question "name 3 centaurs from Harry Potter." I haven't won anything from sheer luck, however.