In order:
1983 Oldsmobile Omega (hand me down, it was sad but it was wheels)
1983 Fiat Spyder Pininfarina (rare FI with AC, PW, incredibly restored)
1991 Oldsmobile Calais with H.O. Quad 4 (awesome for it's day, 180 hp!)
1992 Chevy Cavalier RS 3.1 (wanted a 16v but this showed up instead)
1997 Acura CL converted to 2.2 DHOC VTEC fully built, was a 10,000 rpm animal!
2001 4Runner SR5 4wd (kept 6 months and got bored, traded for corvette.
1998 Corvette, never let me down!
2004 Mitsu EVO 8, 350+ hp, amazing machine
2005 Harley Fatboy, stolen within 6 months
2006 Infiniti M35, really nice grandpa car, got out in 8 months
1997 Porsche 911 993, last of the Air Cooled, loved it, no space for wife and kid at the same time.
2008 BMW 335i, great driver, most unreliable POS I've ever had, and I had a Fiat!
2011 GTI 4-door CW DSG. In love.