If you had to pick the absolute peak of Chrysler's erstwhile Plymouth brand, you'd be hard pressed not to peg it at 1968-1969. Once content courting suburban dads with promises of economy and practicality, Plymouth emerged at the cutting edge of youth car culture — without sacrificing its core audience. A $50,000 check to Warner Brothers meant the company could associate its Road Runner car with the Road Runner cartoon character — a favorite of Cocoa Puffs junkies and crank-shooting speed freaks alike — at once recasting the staid coupe as a viable alternative to the Pontiac GTO. What a difference 38 years makes. – Mike Spinelli

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