1999 Boxster - not fast, but just plain fun
1999/1999/2003 911 - fantastic cars, all of them
2000 Jaguar XJR - 4.0L DOHC Supercharged V8 = giggle inducing instant torque. Wrapped in a sexy body, wood, leather, and chairs that are more comfortable than anything in your house. 
1970 911T - old school charm
1987 951 - boost is like crack
1991 Land Cruiser/1997 Land Rover Discovery - there's something fun about putting around in a real SUV, especially in 10" of snow
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‘07 Mazda RX8
Past: 911T, 911SC, Carrera, 951s, 955, 996s, 987s, 986s, 997s, BMW 5x, C36, C63, XJR, S8, Maserati Coupe, GT500, etc
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