Outrageously Cool Vintage Cars

America's first two-seat sports car, the Corvette was among the first to be made from fiberglass. After crummy sales in the early '50s, Soviet engineer, Arkus-Duntov, modified its V8 engine with a three-speed manual transmission, turning the already good lookin' Corvette into a real performance car.

Made to compete with Ford's Thunderbird, the Buick Riviera—with its aggressive front grill and silky smooth side vents—had a tough-guy vibe that somehow still feels luxe. Boasting the same level of power as its larger Buick siblings but with less weight, the Riviera has serious speed.

In the mid '50s, the Oldsmobile 88 was restyled with longer and lower body shells and wrap-around windshields that made them look a little bit like luxury speedboats. Still, there's no denying that it's one of the handsomest vintage rides around—and with top speeds of 240 mph for Super 88 models, it's a pretty speedy one, too.

With its luscious curves and glinting chrome details, the '62 Shelby Cobra—which the brand (wisely) decided to reproduce for its 50th anniversary—is easily one of the sexiest cars ever built. First-editions can cost in the millions, but the faithful re-creation models come in at a slightly more reasonable $145,000.

It would be hard not to look good behind the wheel of a '59 Austin-Healey 3000 (better known as "Big Healey"). Known for throaty engine rumbles and its elegant and quintessentially British styling, a ride in one of these calls for winding country roads and a scarf tied in your hair.

Ferrari may have only built 350 of their Berlinetta Lusso roadsters, but they certainly left their mark on the industry. Beneath that classic "touring" exterior beats the heart of a real road racer. To wit, one of the few original owners included Steve McQueen, whose speedy 1963 Lusso went for $2.3 million at Christie's in 2007.

Few cars emanate the same rugged, snarling American cool as the '66 Ford Mustang, which was made famous by the Steve McQueen movie Bullitt. Of course, if you're seriously considering buying one, classic red is the preferred paint job for a pony.

In the mid '70s, GM produced its final muscle car, the GTO Judge, a tough, masculine beast with a sloping back window and long, pointed nose. Like its name suggests, this ride commands authority wherever it takes you.

With fans including Enzo Ferrari (who dubbed it "the most beautiful car ever made"), the Jaguar XKE is the pinnacle of muscle car style. Produced in several versions including "Lightweight" and "Low-Drag" editions, this gorgeous car drives as good as it looks.

Standing for "super leicht" (or "super light"), the tiny frame of the Mercedes SL belies its sturdiness. Often nicknamed "pagodas" for their oddly-shaped roofs—which sink down in the middle—SL models are a crucial chapter in Meredes' history of top-notch performers.