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    11. Wilco - "Outtasite (Outta Mind)"

    Year: 1997

    Whether or not it’s actually Wilco skydiving while playing their song is irrelevant really, it still made for an awesome video. It’s impossible not to have a good time just watching them do this. And the best part about it is, I’m sure Wilco didn’t think, “What would it cost and why wouldn’t it work?” They probably just said, “Let’s do it.”