I've won a lot of things. Not as many as some people I know, but I have had good fortune when it comes to contests. I've won an iPad from Neatorama, a signed Manny Pacquiao-Antonio Margarito boxing glove from Time Warner, and various other things from other groups: DVDs, movie tickets, magnetic toys, various kitsch, and a lot of free beers at pubquiz. I've also "won" things that have turned out to be less exciting, like a free trip to Vegas that was not free, or a signed basketball from Cricket Wireless that never actually materialized.
But overall, my luck with contests has been awesome. Sometimes it's just because I'm in the right place at the right time, as was the case for the first contest victory I ever won. I was very young, listening to Oldies 94.5, a station that no longer exists (in 2000, they switched frequencies with The Buzz, which still exists, and in 2006 and 2009 changed call signs and formats), and they had a contest that I happened to hear, at the right time that I happened to be whatever number caller they wanted.
The three songs, "Proud Mary," "Along Comes Mary," and a third song I cannot recall, had a common theme (hint: they all had the name Mary in the title), and I was asked to name that theme (see previous hint). I did so, and won!
The prize was awesome: two free movie tickets and $50 to a restaurant. I don't remember what restaurant though I think it might have been a steakhouse. And with the movie tickets, I went to see Galaxy Quest, which of course was awesome.
I'm not quite convinced that I was actually old enough to win a contest, and I have to think the radio announcers probably thought I was a woman. Every contest I've won since has made it clear that there is a minimum age to win (usually eighteen or sometimes twenty-one) and the idea that a pre-teen can win a radio contest clashes with this.
Nonetheless, it was an awesome start to what has thus far been a pretty successful contest record. Thanks, KLDE, even if you're long gone.