I entered a contest to win a Gameboy pocket some Pokemon games for Kids WB back in the day. I got a runner up prize, which was a transparent super ball with a Pikachu figure in the middle.
Also I won a 3DS from a Stack 'Ems machine. This particular machine only needed on quarter so I thought, why the hell not? After I had won, I accidentally chose the wrong prize, some Beats by Dre headphones, but the guy managing the place was nice enough to let me switch it for the 3DS instead.