1955 Mercedes-Benz 300SL Gullwing

The R107 SL is what happens when Mercedes builds a sports car for grown-ups. Where the 300SL was a race car with plates, the R107 was a gentleman's express — fast enough, comfortable enough, and built like a bank vault. It ran from 1971 to 1989, making it the longest-produced Mercedes model ever. While American manufacturers were fumbling through the malaise era with smog-choked engines and questionable build quality, Mercedes just kept refining the R107. The 450SL hit the sweet spot: enough V8 torque to move with authority, none of the early emission-control headaches of the smaller engines, and all the presence of the big-dollar 560SL without the collector premium.

The W123 is the car that built Mercedes' reputation for indestructibility. Specifically, the 300D turbodiesel became the unofficial taxi of the third world, the eco-warrior's grease-car conversion platform, and the ultimate proof that German engineering could laugh at the odometer. These cars routinely hit 300,000, 400,000, even 500,000 miles with original engines. The OM617 five-cylinder turbodiesel is considered one of the most reliable engines ever built. While American cars were being strangled by early emissions equipment, the W123 diesel just kept clattering along, sipping fuel and refusing to die. The stacked headlights became an icon — a look that said 'serious car, serious engineering.'