My Date with Drew (2004)
This was delightful. A financially strapped, aspiring filmmaker in L.A. uses the winnings from a game show ($1100) and a video camera purchased from Circuit City on a friend's credit card (with the intention of taking it back in thirty days to take advantage of Circuit City’s return policy) and tries to get a date with Drew Barrymore. A couple of his friends help him document his attempts. It’s funny and kind of amazing and inspiring. I loved it!