9. Cadillac Cimarron

Cadillac tried to win over younger drivers with the Cimarron, but the plan quickly backfired.
Essentially a dressed-up Chevy Cavalier, the Cimarron lacked the luxury, performance, and refinement expected from America’s premier luxury brand.
The move didn’t just fail to attract new customers—it also damaged Cadillac’s reputation for years to come, serving as a classic example of misguided badge engineering. Source: Autoweek