I stil have my '69 Mustang convertible that I bought when I was in High School in 1987, so that kind of fits the bill for me. If I were to have the opportunity to get a true Dream Car, it would probably be one of those Superformance GT40s. The new high performance/supercars are really amazing feats of engineering, but I feel with all the new tech, comes a loss of the driving experience. My cousin has one of the new Corvettes, it's fun and cool as hell, but while riding in it, it feels like a lot of other new cars.
So, if I were to buy another car that was an occasional driver that I just wanted to have fun in, I'd want something more loud, raw and definitely a clutch and H-pattern shifter.