By the mid-1960s, Oldsmobile had a branding problem hiding in plain sight: the word “old” sitting right in its own name. The company’s answer wasn’t a rename, it was a full reinvention built around the 4-4-2 option package, a livelier Cutlass lineup, and advertising aimed at buyers who had never considered an Oldsmobile before. Read on to find out how a brand built for retirees ended up building some of the era’s most collected muscle cars.