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We’re taking one last trip down automotive memory lane. Across the world, millions of cars have been produced, but only of few have stood the test of time to become classic car icons. We’re compiling a list of the 10 coolest classic cars of all time based on industry impact, rarity, power, and style.

1966 Shelby 427 Cobra

1966 Shelby 427 Cobra - carsforsale.com
1966 Shelby 427 Cobra - carsforsale.com

The Shelby Cobra was great, but the 1966 Shelby 427 Cobra is certainly one of the coolest classic cars of all time. This classic car was yet another beautiful machine from Carroll Shelby, and only 23 Cobra 427s were ever produced. Supposedly, this machine could drive from 0 to 100 mpg AND come to a complete stop in under 14 seconds!

1957 Mercedes 300 SL Gullwing

1957 Mercedes 300 SL Gullwing - carsforsale.com
1957 Mercedes 300 SL Gullwing - carsforsale.com

Rocking gull wings before it was cool, Mercedes-Benz pioneered gull wing doors in the beautiful Mercedes-Benz 300 SL Gullwing. This Mercedes was largely successful, and it’s extremely collectible today. In bold at the top of this vehicle’s resume, it was considered the fastest production car at the time.

1969 Ford Mustang Boss 429

1969 Ford Mustang Boss 429 - autowise.com
1969 Ford Mustang Boss 429 - autowise.com

Less than 1400 original Ford Mustang Boss 429s were built. Ford wanted to develop a Hemi engine for NASCAR to compete with Chrysler’s powerful 426 Hemi. While the Boss 429 was only rated at 375 hp and 450 lb ft of torque, some auto experts suggest it could easily produce greater than 500hp. Ford had to adjust the body and remove AC just to fit this giant engine.

1959-60 Cadillac Eldorado

1960 Cadillac Eldorado - carsforsale.com
1960 Cadillac Eldorado - carsforsale.com

Though the American luxo-barge would continue on for the better part of three decades, it reached a high watermark with the 4th generation Cadillac Eldorado back in 1959. It was large, sumptuous, and ostentatiously styled. The chrome, that grille, those headlights, those taillights! Fins had been getting bigger and more elaborate as the 1950s had gone on, and the Eldorado’s fins, complete with the “rocketship” double-bullet taillights, were never to be equaled or surpassed.

1970 Plymouth Hemi ‘Cuda

1970 Plymouth Barracuda - carsforsale.com
1970 Plymouth Barracuda - carsforsale.com

The Plymouth Hemi ‘Cuda (Barracuda) packed Chrysler’s 426 cubic inch 7.0L Hemi V8. The Barracuda was Plymouth’s first pony car. From 1970 on, the ‘Cuda was built on an E-body, establishing its own look and feel among the competition. These are some of the most valuable and collectible muscle cars today.

1966 Corvette Stingray 427

1966 Corvette Stingray 427 - carsforsale.com
1966 Corvette Stingray 427 - carsforsale.com

The Chevrolet Corvette C2 began in the model year 1963. It was a beautiful upgrade from C1 Corvettes. In 1966, Chevy offered an impressive 427 cubic inch big block V8 in their Corvette. Some Vette fans still think the C2 was the best-looking generation to date.

1984-96 Ferrari Testarossa

1990 Ferrari Testarossa - carsforsale.com
1990 Ferrari Testarossa - carsforsale.com

It doesn’t get more 80s excess than the white ‘86 Ferrari Testarossa driven by Don Johnson in Miami Vice. Like all proper Ferrari, the Testarossa featured a V12, a 4.9L in this case, paired to a 5-speed manual. The Testarossa is a single car collection of our favorite classic car designs including pop-up headlights, automatic seat belts, and a directional dome light (like you find in commercial airplanes).

1970 Chevrolet El Camino

1970 Chevrolet El Camino - carsforsale.com
1970 Chevrolet El Camino - carsforsale.com

Admittedly, we may be stretching the definition of “cool” for some of you, but there are people who unironically think of the El Camino as a cool classic car. And when it comes to the 1970 Chevy El Comino SS, you can count us among the converted. Among the engine options in 1970 was the monstrous 454 ci LS6 V8 making 450hp and 500lb.-ft. of torque. Add in those racing stripes down the middle and the six-foot bed and you’ve got a legit and unique classic of the muscle car era.

1989-91 BMW Z1

1988 BMW Z1 - netcarshow.com
1988 BMW Z1 - netcarshow.com

The BMW Z1 is the car that started the German version of Z cars. Sure, it wasn’t even sold in the US, but this car represents all that is weird and quirky about 1980s sports cars, and that qualifies it as super cool. The Z1 featured the same engine as the 3-Series of its day, a 2.5L I-6 making 168hp. But it isn’t the engine or its performance that the Z1 is remembered for. No, it’s the Z1’s unique slide down doors. Though this wasn’t super practical, as it forced driver and passenger to hurdle over the high door sill to get in, it sure looked cool. And in the 80s, that’s really all that mattered.

1948-66 Porsche 356

1960 Porsche 356 - carsforsale.com
1960 Porsche 356 - carsforsale.com

Legends don’t spring out of nowhere, and the Porsche 911 is no exception. The greatest sports car of all time traces its linage directly to Porsche’s preceding roadster and their first production car, the 356. The aerodynamic, rear-engine two-seater was designed by Ferdinand Porsche and debuted in 1948. It began it’s run (lasting all the way to 1966) with a modest 1.1L 4-cylinder air-cooled naturally aspirated boxer engine and a four-speed manual transmission. With their sleek design and rear engine set-up its easy to see the family resemblance to the 911. Today, 356s are a major collector’s items for Porsche fans. A Porsche 356A 1600 Speedster auctioned at Sotheby’s in 2016 went for $665,500.

Editor’s Note: This post was originally published in December 2015 and has been completely revamped and updated for accuracy and comprehensiveness.

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Chris Kaiser
Chris Kaiser

Chris’ greatest passions include topiary, spelunking, and pushing aging compact cars well past 200,000 miles on cross-country road trips. His taste in cars runs from the classic and esoteric to the deeply practical with an abiding affection for VW Things, old Studebakers, and all things hybrid-crossover.

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