First car: 1986 Ford Taurus Wagon. $2k at the time, pretty bombproof and cheap to repair. A lot of fun during Vermont winters with snows on the front wheels only (that whale tail would pass you if you weren't careful). I'm still a wagon-loving freak:
Second car (my first independent purchase): 1993 Subaru Legacy Sport. My first turbo, first manual transmission
A lot of car- probably overpaid, but rare and it went like stink (WRXs weren't available in the US yet):
Third (first bought new): 2003.5 Mazdaspeed Protege. Horrible color, but got $5k off sticker because of it. Fast, fun, and a bit silly. No cruise control (!). Doesn't match my personality, so didn't last long...
Fourth: 2005 Saab 9-2x Aero. Cheaper than a WRX, better dealer service, too. GM were throwing money at consumers to get these off the lot at one point, so I bit. Tuned it a bit, drove it like an arse at times, got horrific mileage for the most part. The seats weren't very comfortable either- the main reason I sold (plenty of 5-7 hour drives out here in the desert):
Current: 2007 Saab 9-3 SportCombi 2.0T. Everything I need. Peppy turbo'd engine, manual transmission, enough room to throw my road bike in the back with both wheels on, mountain bike with front wheel removed. 30mpg @ 80mph. Cheap to insure. 40k miles and fewer issues than the Mazdaspeed or Saabaru. Fell off the truck on its way to me from Salt Lake City. Frightening depreciation, though:
Just for fun: We lifted my girlfriend's 2005 Subaru Outback Sport (Impreza). 9.5in of ground clearance with Forester springs and wheels.
Surprisingly capable on moderately nasty dirt roads: