Creative Nomad Jukebox. $500, used it for one trip, not even as much as I though I might on that trip and didn't use it too much after that.
$150 Bass Guitar Practice Amp - The sound is so terrible, it's not worth playing.
I have some other things that I payed quite a bit of money for that have been underused, but I wouldn't call them my worst purchases ever. Oh for the days when I had money to spend but didn't invest it in things that would retain their value.
Worst Non-Purchase - not buying a house when I got married in 2004. My wife and I thought these brand new houses were too much at 190,000. Had we known prices were going to go up so much, we could have made something work, and we'd be sitting much prettier now.
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