When I was a little kid and everyone was into Webkinz, I won one of the digital-exclusive Webkinz by submitting an essay to them. Um... A few months ago NOW! That's What I Call Music had a contest leading up to the Grammys where you could win Adele merchandise all week. I won once that week and then later on in the week I was the only one that entered (and I entered under like, 5 different accounts), but they just decided no one would win because they didn't think that was enough people, which they failed to tell us.

Anyways... I won
Live at the Royal Albert Hall, which I already had, although this one was slightly different because it was altered in size and format because it was in a CD case rather than a DVD case. I also won a Best Costume contest at a horror film festival earlier this year (well, technically last year, 'cause it was October 2013) for my James Bond costume. I won an Amazon gift card.
