Top 10 Coolest Classic Cars of All Time

top 10 coolest classic cars of all time

To wrap up Classics Week at Carsforsale.com, 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

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!

Shelby Cobra

1957 Mercedes 300 SL Gullwing

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.

1957 Mercedes 300 SL Gullwing

1969 Ford Mustang Boss 429

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.

1970 Plymouth Hemi ‘Cuda

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.

plymouth hemi cuda

1968 Plymouth Road Runner Hemi

Plymouth packed the same 7.0L Hemi V8 in the Road Runner, its mid-size performance car. The company allegedly paid $50,000 to Warner Brothers to use the likeness and name of the Road Runner cartoon. Having one of the best engines of the muscle car era, the Road Runner is easily one of the coolest classic cars of all time.

 Plymouth Road Runner Hemi

1969 Chevrolet Camaro ZL1

The most legendary Camaro of all time is the ZL1. The story behind the Camaro ZL1 is impressive. Only 69 of these Camaros were produced with the all-aluminum 427 V8. Experts agree these cars were capable of producing around 550hp, despite the initial rating of 425hp.

1969 chevrolet camaro zl1

1964 Pontiac GTO

“Little GTO, you’re really lookin’ fine.” While writing the song GTO, Ronnie & The Daytonas probably didn’t know that we would still be thinking the same thing about the original Pontiac GTO 51 years later. Although GM had a ban against placing big engines in small cars, Pontiac ignored this rule when creating the GTO. After great public response, it won over GM executives, paving the way for a collection of other great GM muscle cars.

1964 Pontiac GTO

1969 Ford Mustang Mach 1 428 Cobra Jet

While the Mustang Mach 1 428 Cobra Jet is sometimes forgotten in the sea of cool classics, but it’s certainly worthy of recognition. The Mach 1 has a larger engine bay to accommodate big block engines. Combine the cool classic Mustang look with a 428 Cobra Jet engine, and you’ve got one of the coolest classic cars of all time.

Ford Mustang Mach 1 Cobra Jet

1962 Jaguar E-Type

In the same way many women swoon over David Beckham, the international automotive community is swooning over this car. The E-Type is a British sports car for the ages. Enzo Ferrari called it, “The most beautiful car ever made.” Mr. Ferrari wasn’t the only one to love this car. It also earned 1st place in The Daily Telegraph’s 100 Most Beautiful Cars of All Time.

1962 Jaguar E-Type

1966 Corvette Stingray 427

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.

1966 Corvette 427

What’s the coolest classic car of all time? Let us know what you think in the comments below!