OH MAN!
OK, for Christmas and graduation I traded my Daewoo Wagon for a brand new 04 Nissan pickup (the small one). Had another Nissan p-up bought new in 88, and got 300 thousand miles before I traded it on the Daewoo. Daewoo went out of business about the time I bought, and the car began costing a lot more to upkeep than the p-up ever did. Best part, as a recent college grad they gave me a sweet deal! Love my truck!
Of cars I've had in the past, my favorites for fun to drive would be my first two, a 71 Toyota Celica, a screamin' little go-cart!, and a 62 Chrysler New Yorker that lit up like a jukebox at night.
While I love the little two seat roadsters, I would have to disagree about two doors "only" looking good topless. I love the old phaetons, especially from the 30's. Give me a Doosey any old time. Of course, the Lincoln Continental made a phaeton (4 door drop top with suicide doors in the rear) in the early 60's that looked pretty cool. Next after a 34 Duesenburg, my wish list would have to be a 70 Daytona Charger, and a 60 Thunderbird (4-seater), or an XKE Jaguar (hardtop!, that's one convertible I don't care for). I like most all of the old muscle cars from the late fifties through the early 70's. Anybody remember the Rambler Marlin? Used to have one, they're really cool looking, but I haven't even seen one on the online auto auctions.
There aren't a lot of newer cars I care for, they all looked the same for so long. The new Nissan Z roadster is pretty cool looking, but looks like a nightmare (read: $$$) to mechanic. The last two cars I really liked the looks of are the Cadillac Allante, and the Buick Reatta, both limited production and short lived. Oh, I forgot the new Cadillac "corvette" XLR, wouldn't mind one of those. Ah, maybe one day...