1986 Glassport 165RX - it was 16.5 feet long, inboard/outboard, with an OMC Cobra outdrive that gave me problems CONSTANTLY, floors that were starting to give out, a big dent in the side where I hit a buoy at night, and half the gauges didn't work. With that said, I bought it in college as a repo for $1,000, built the tower for it myself, and never in my life have I had more fun on a boat. Some of my best memories ever were made on that boat, including when it'd break down at night. I had it for 4 years and sold it for $200 more than I paid for it and still wish I never got rid of it.

In college I was on the UT ski/wakeboard team, which was sponsored by Mastercraft, and I was an officer which meant I had keys to the boat and could take it whenever I wanted it. We got a new one every year and I was on the team for 3 years, so I kind of had:

'05 MC X-7
'06 MC X-7
'07 MC X-15

In '08 I bought my '05 Supra Launch 24SSV and she's a great boat and we've already made some great memories.