Get an MX-5.
Mazda has an amazing history with the MX-5, and as long as you're man enough to handle a few people saying 'dude, that's a chick car', then you're going to have the most fun legally allowed on four wheels. The resale is one of the best out there - look up an early 90's model in good shape, you won't find one in good shape for under $5K. They're cheap to own and fun to drive, only drawbacks could be 1) cozy interior, not much room for 'stuff'. 2) soft-top convertible, depends on your preference and where you live. 3) Stupid people call it a chick car. It isn't. They have flocked to the VWs, Cute 'Utes, and Mustang convertibles.
Don't take my word for it, check out Motor Trend, where they found it was more fun than a brand-new 370Z, a Shelby GT500, and even a ZR1.
http://www.motortrend.com/features/p...x_5_miata.html