Mercedes-Benz 190SL (1955–1963)
Now that prices of the Mercedes's iconic 300SL Roadsters are securely in the stratosphere, interest has shifted to that radical car's less complicated younger brother: the four-cylinder, 190SL. "Though it had half the power of the Gullwing," Gooding says, "it looks nearly just as good." Gooding credits its up-and-comer status to the fact that it is "viewed as a great starter classic from a great brand, with excellent reliability and access to parts and technical support." 300SLs routinely sell in the $700,000 range, but Gooding recently sold the debonair '57 190SL pictured here for the bargain price of $198,000.