When Hugh Hefner first asked out singer Barbi Benton, she supposedly said, "I've never been out with anyone over 24." "Neither have I," Hef replied.

We should all be so lucky.

When it comes to cars, however, it's easier to get fired up over mature curves. Contemporary rides are obviously miles ahead in terms of power, handling, gas mileage, and technology. But they lack the intangible mojo that made these landmark vehicles timeless. Here are 10 classic American cars that left a permanent mark on the automotive industry.

1 - 1953 Chevrolet Corvette

The Corvette was America's first two-seat sports car. To some, it's still the only sports car worth owning. What began in 1953 as a slow performer in the showrooms and on the street soon gained momentum and V8 power, and it evolved into an American icon. To desire a 'Vette is only human. To own one is to belong to a family as passionate for their cars as any you'll find. Each generation of Corvette has been better than the last, and all represent passion molded in fiberglass.

Cool Fact: Red is the color we usually associate with the 'Vette, but in 1953, white was the only color offered.

2 - 1955-1957 Chevrolets

By the end of 1954, the Corvette was on financial shaky ground, but it still had style and showed promise. The same couldn't be said for the rest of Chevy's lineup, the members of which all looked much the same as the 1949 model and loped along on six cylinders. That all changed in 1955.

Chevrolet's redesign was modern yet tasteful. The best part of it was the debut of the small-block V8. From there, the '56 got a nose job. And lightning struck a third time with the legendary '57. The tri-five cars each have their own unique look and loyal fans, but together they embody cruising like nothing else.

Cool Fact: If the "regular" versions weren't exclusive enough for you, there was always the Chevy Nomad, a rare two-door wagon.

3 - 1966 Ford GT40

Who says that great things don't come from hard feelings? When talks broke down regarding Ford's prospective acquisition of Ferrari in the '60s, the Blue Oval guys became fixated on humbling Enzo at Le Mans. With the dedication of Carroll Shelby and his crew, they did just that with the GT40, beginning in 1966. This mid-engine car was equally brutal and beautiful, and the new Ford GT's lines look almost tame by comparison.

Cool Fact: You gotta love the "Gurney Bubble," that little raised roof section first installed over the driver's seat to accommodate team racer Dan Gurney's height.

4 - 1948 Tucker

The Tucker is a great underdog story and an even better car. In the late 1940s, Preston Tucker decided to build a better car, and the Big Three took notice (some say they did more than take notice, but that's another discussion). Tucker clearly succeeded in his goal to develop a better, safer car. It rode on a four-wheel independent suspension. The innovative safety features continued inside with a padded dash and the "crash cowl," an area for the front passengers to duck into before an impending collision. Furthermore, a Cyclops-esque center headlight rotated with the front wheels.

To the rear, the Tucker's horizontally-opposed six-cylinder pushed the car to an impressive 120 mph. Too bad Tucker's dream came to a halt after just 51 models had been built.

Cool Fact: If you've seen Star Wars: Episode III -- Revenge of the Sith, you may notice that Senator Bail Organa's (Jimmy Smits) ride was inspired by the Tucker.

5 - 1948-1986 Jeep CJ

It's tougher than a car, more nimble than a truck, and it helped win World War II. How freaking cool is that? For decades, the Jeep CJ represented rugged individuality and a sense of adventure. It wasn't known for its speed, and even less so for comfort. But that wasn't the point. "It's a Jeep thing... you wouldn't understand," as the saying goes.

With the Jeep CJ, you could ditch the top and doors, fold the windshield and go for it. When you were done playing, you could hose the exterior and the interior. Try that with your Navigator.

Cool Fact: Without Jeep, it's debatable whether or not SUVs would have ever caught on.

6 - 1969 Dodge Daytona/1970 Plymouth Superbird

Not many guys can claim their car was too hot for NASCAR, but you can if you own a Dodge Daytona or a Plymouth Superbird. They were even wilder than the original models form which they evolved -- the Charger and Road Runner. The Daytona and the Superbird could really fly, but their elongated snouts and sky-high rear wings kept them planted. No one really knew it at the time, but they were the apex of the muscle car era; and like that period, they were gone too soon after NASCAR rule changes made them obsolete.

Cool Fact: Buddy Baker took his Daytona just over the 200-mph barrier at Talladega, a record that stood for 13 years.

7 - 1964-1970 Ford Mustang

We can forgive Lee Iacocca for the Mopar K-cars. He's the father of the Mustang. When it debuted in 1964, everybody -- really, everybody -- wanted one. Huge lines formed at dealers just to see one. Equally big lines formed to actually buy one. Dozens of options allowed the driver to equip it from mild to wild without breaking the bank.

And it wasn't long before Carroll Shelby lent his magic touch to some truly special editions. Oh, and can you say Bullitt without thinking Mustang?

Cool Fact: The earliest Mustangs, known as 1964 models, didn't have adjustable passenger seats.

8 - 1964-1970 Pontiac GTO

Years before he crafted Michael J. Fox's Back to the Future wheels, John DeLorean quietly created what many consider to be the first serious muscle car. It may have been a Tempest on steroids with a name lifted from Ferrari, but the GTO was like nothing else. Its looks alone made you think twice about trying to outgun it. If that didn't do it, the Goat's unruly horsepower would give you ample opportunity to check out the back end as it pulled further ahead of you.

Cool Fact: The GTO clearly violated General Motors' restrictions on racing and power-to-weight ratios at the time of its development.

9 - 1959 Cadillac

Here's a car that can be described in just three words: tailfins, tailfins and tailfins. No doubt the resulting huge blind spots caused some VWs to be swatted aside during lane changes. Maybe that's why tailfins simmered down in the following years -- or maybe it was a secret Big Three treaty that was responsible. Whatever it was, this car marked the end of an era in automotive design.

A gaudy way to go out? Sure. But today, it's a huge part of this car's timeless appeal. When you have a car as unapologetically big and bold as a '50s Caddy, why be modest?

Cool Fact: If you can force yourself to quit staring at the tailfins, move your eyes a little lower. The '59 had another unique design element: The front grille design was mimicked in the rear.

10 - 1949-1951 Mercury Coupe

What other car looked like a chopped-top, lead sled straight from the factory? While the other guys' cars looked more liked warmed-over pre-war models, Mercury cut down the greenhouse and smoothed the sides of theirs. It's one of the earliest designs that gave the illusion of speed even while at a standstill. A few years later, its popularity grew even more when it becomes the ride of choice for James Dean in Rebel Without a Cause.

Cool Fact: The slightly-modified Merc in Rebel is rumored to have been an early project of famed Hollywood customizer George Barris.

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