1st - 1978 Chevy van. Bought it brand new off the lot after working a killer summer job. Paid $5900 cash. Spent the winter customizing it... stereo, bed, custom paint, windows, all of it. I drove that from age 18 to 22 and I swear on a bible if I had one, I got laid easily 500 times in that 4 years (not 500 different women, just 500 times).
Now... 2004 RX8