96 SS (now Team LoPrep's whip). Torque, looks, stoopid reliability, not common, highway hero, better than expected handling. You think it's just a Caprice, and it is... but it isn't.
95 F250 Powerstroke. Stripped down, radio delete, rubber floors. I bought it with 40k, put 100k completely trouble-free miles on it, collected three insurance checks on it from fender benders but never fixed the dents, towed 10k lbs for easily 75% of my use, never had to replace even a brake pad. The A/C would fog up the outside of the windows on a 100 degree day. I sold it for more than I paid.
Already posted about my 87 Cutlass Salon in the other thread. 140hp of marshmallow, but it was reliable, easy to work on, and looked like a million bucks. Little old lady car. I found this one on the back lot of a dealer ready to be auctioned off, so I saved them the transport costs and gave them what they would have got at the auction and drove away. I think I bought it with 36,000 miles.
83 Baja 190SS. This boat was so bad when I bought it, it had grass growing out of the motor stringers. It was one of those "trailer $1000, must take boat." I built a Vortec 350 for it expecting they typical heavy, 1978 Cadillac feeling you get from most I/Os. I didn't get that. That thing was wicked fun. 65mph with four people, open exhaust, and just enough weight to keep handling fun.
73 Impala S/W. Bought it sight-unseen from 1400 miles away and did a rent-and-drive. Ran when parked on it's nylon bias-ply tires. 454, A/C and no other options. Built a 468 for it and drove it cross country four times gettting 9mpg. I towed 10k lbs with it a few times, and once filled the cargo area with concrete parking curbs. It was the "truck" that replaced the F250. It was like driving a couch.
Scion xB. What it lacked in power it made up for in off-the-wall usefulness. Great MPG, zero repairs in 200k except for a hatch latch that broke, and just fun to drive. The only reason it isn't on the road still is because my ex couldn't afford a radiator so she sold it to a college kid.