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The original “businessman’s hot rod” combined a racing pedigree with luxury trimmings

When people boasted of the performance of Chrysler-branded automobiles during the postwar years, it was usually in reference to the cars’ mechanical prowess: smooth and reliable, just like a luxury vehicle should be. Naturally, powerful acceleration was a key element, but it was intended to make premium models more capable on the road, and not meant for speed contests. The corporation’s other divisions were better equipped to manage a young buyer’s stoplight-sprint antics.

Part of that perspective changed when the division released the C-300 in 1955. Fitted with the 300-hp, 331-cu.in. “FirePower” V-8 capable of pushing it to a top speed of 130 mph, the specially trimmed hardtop coupe broke the mold while redefining the parameters of a luxury coupe. Adventurous CEOs could feel the excitement of raw power while seated in a luxurious cabin, surrounded by coachwork that spoke of edgy—yet not audacious — exclusivity. And it was exclusive: Just 1,725 were built in the first year, each costing $4,110 (or $40,095 today) without options.

More compelling was how the C-300 began to cement its legacy beyond the boulevard. Trimmed for racing, it utterly dominated the NASCAR and AAA stock car ranks, which continued a year later with the updated 300B. For 1957, the 300C set a notable production car speed record at Daytona Beach before the Chrysler division took a bow and left the business of racing to Dodge and Plymouth, prior to the AMA embargo.

Although the on-track exploits may have been put to rest, the exclusive “Letter Cars” remained in production, continuously improved both visually and mechanically. The model’s evolution took a significant leap forward when the 300F was introduced in 1960, the basic elements of which carried through to the 300G of ’61, with attributes that not only set these cars apart from their predecessors but have attracted both collectors and vintage-car driving enthusiasts alike since. If you’ve been considering the purchase of one, here are some things you should be aware of

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