For fun: I'm with Matt on the SWRT STi. Fun = dirt roads.
Weekend track: 22b STi
Daily driver: Spec C STi
For the wife: '06 WRX (for the AWD and moderate horsepower)
The Showoff-Mobile: '67 Shelby Cobra GT500 in blue w/ white racing stripes, or
black, fully restored '71 Corvette Stingray w/ 454ci big block V8. Tough call. Probably the GT500, just because I see too many assholes in 'Vettes.
Winter: I like that Forester STi
I don't wanna blow all my money on wildly expensive luxury cars - I'd like to have some left for gas and racing rubber