First car: 1977 Chrysler New Yorker
Took that the day I bought it, at the tender age of 16...
1989 Chrysler LeBaron (brand new in '88 - Traded in the New Yorker on it... I was in the Navy and stupid. Sold it for a huge loss just to be rid of the thing when I got out.)
Following this I got into small race cars:
1972 X 1/9
1973 914
1972 240Z
1977 280Z
1981 Lotus Esprit turbo
1988 300zx
(see a trend here?)
Eventually I moved to Virginia in the late 90's and the dotcom happened, and things got a little crazy...
1966 Mustang street rod (I thought I wanted an American Classic, I was wrong - sold it two years later)
1994 F350 dually 4-door (used to move my 28' Scarab around)
1998 300zx TT
Eventually the bubble burst and I moved back to Colorado...
2006 PT Cruiser GT (Always been a Chrysler guy, so this was inevitable...)
2010 Jeep JK Rubicon (Keeping it in the family; nice trade-in value on the PT)
2012 Chrysler 300 SRT (Still in the family for the trade-in. Another land yacht - I thought I'd learned my lesson but I guess not.)
2014 Fiat 500 Abarth (Still in the family, though estranged... The cost difference between this and the SRT 300 as a trade-in actually made me some money. Still have this.)
2016 370Z (still have. I finally got out of the Chrysler Cycle.)
The best of the lot? Hard to say... A toss up between the 914 (raw driving fun in Bermuda shorts) and the 370Z (raw driving fun in business casual)