Porsche 550 Spyder
Of all the Kennedyesque curses to befall Porsche – the shunned 928, the ridiculed 914, the fact that the name of their longest-running model, the 911, now reeks of disaster – none has been more destructive than the 550 Spyder. This is the car in which James Dean had his fatal crash. Somewhat less important, this is also the car that set Porsche back 40 years.
Developed expressly for racing, the 550 Spyder was Porsche's attempt to move toward a mid-engine design. The advantages of placing the motor in the middle of the car, rather than hanging it off the back, are myriad, and also vaguely dull and scientific. But it comes down to this: Cars simply handle better when they carry their weight between their axles.
The Spyder's layout necessitated a novel Porsche design language. With its engine and driver positioned amidships, the 550 had a lovely symmetry to its front and rear ends and a lithe, visual weightlessness that telegraphed Porsche's new engineering direction.
But it was not to be. After Dean lost it at the junction of California's highways 41 and 46, Porsche nixed the Spyder. It would be another four decades before the car maker began putting engines in the right place, in cars such as the Boxster, the Cayman, and the Carrera GT, all of which owe a debt to the 550.
What to watch out for: These cars are so rare (Porsche built only 90), and all are so meticulously restored, that there isn't much to worry about other than the funding. Besides, cars this expensive don't get driven anyway.