In 1969, Oldsmobile faced a conundrum that would tickle any marketer’s funny bone: how do you convince a youthful crowd to buy a car with “OLD” in its name? As the century rolled onward, General Motors’ upscale buyers were starting to show their age, leaving Oldsmobile’s sales team sweating bullets. But rather than let their brand become a relic, they embraced the irony, trying to flip the script and turn Oldsmobile into the “Youngmobile.” After all, who doesn’t love a good underdog story?