15 Classic Cars That Define Cool

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We’ve overheard guys say they don’t care what kind of car they drive as long as it gets them from Point A to Point B. Those guys are liars. Who wouldn’t want to own a car that turns more heads than a bikini car wash? Maybe these guys have only driven used jalopies and don’t know anything else. Well, these are the cars they should know. These are the 15 Classic Cars That Define Cool.

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1966 Shelby 427 Cobra

Anything attached to Carroll Shelby’s name is immediately worth your time. With an insane power-to-weight ratio, the Shelby 427 Cobra has a bit more giddyup than your Corolla. Plus, the hundreds of thousands of dollars you’d pay for one will seem like chump change compared to the $5.5 million shelled out for the ’66 Shelby 427 Cobra Super Snake.

1961 Jaguar E-Type

Whether you pronounce it Jagwar or Jag-u-ar, everyone agrees the brand oozes style. The E-Type was released in 1961 to some pretty heavy praise. If Enzo Ferrari referred to it as, “The most beautiful car ever made,” well, that’s good enough for us.

1969 Maserati Ghibli 4.7

The aggressive shark-shaped nose on the Maserati Ghibli is enough to place it firmly on this list. Plus, the Maserati name earns it plenty of clout. Basically, this car is what the Mazda Miata dreams of becoming as it falls asleep at night.

1964 Aston Martin DB5

If it’s cool enough for Bond, it’s cool enough for us. If you had to pick one vehicle that James Bond relied on the most, you’d be hard-pressed not to go with the DB5, and the one from Goldfinger would look pretty sweet in our garage next to the cans of beer and lawn care products.

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1957 Mercedes 300SL Gullwing

The doors are only part of the reason this is one of the coolest cars to ever hit the pavement. The fact that the 300SL was the fastest production car at the time, means driving to your ad meetings in Manhattan wouldn’t be a bore.

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1969 Boss 429 Mustang

You know you’re getting some sick power when they have to change the body of a Mustang just to accommodate your freakishly large engine. How could you not want to roll down the windows and listen to that sucker as you were cruising around? (Which would be a good idea since, due to the size of the engine, they couldn’t fit in any air conditioning.)

1963 Corvette Sting Ray

While nothing was wrong with the Corvette prior to ’63, when the Sting Ray rolled out it made the previous models look like chopped liver (fast & still somewhat attractive chopped liver). Besides the new look, the C2 Corvette was a bit lighter and handled far better than its predecessors. While some nice stylistic changes would be made in the coming years, there’s something about being first.

1969 Ferrari Dino 246 GT

Far too often cars are rigid. The lines and angles are harsh and, unless there’s something crazy under the hood, they become a complete clone of something else. The soft lines on the Ferrari Dino 246 GT tells us this car is meant to be driven fast and playfully. If we had one, we’d oblige.

1966 Alfa Romeo Spider Duetto

Something about this car just makes us want to drive the Italian countryside while occasionally stopping to drink local wines. Plus, any time you can get a car with style AND storage space, well you just hit the jackpot my friend. It’s perfect for storing all the sheets of paper with phone numbers on them.

1969 Dodge Charger

If there’s one thing we know about the ’69 Charger, it’s aerodynamic. At least that’s what we learned from Bo and Luke Duke. The ’69 Charger is a thing of beauty whether it’s a General Lee or not. It may never get the billing its Mustang counterparts always do, but the fastback look and all American style will never go out of fashion.

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1966 Lamborghini Miura

We don’t know if it’s the most stylish car on the list, but as far as cred goes, well it inspired the whole “Let’s toss a couple of seats on a rocket” sports car idea. It also became a new and different Italian sports car option outside of the Ferrari’s of the world for auto enthusiasts at the time.

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1969 Toyota 2000GT

If you’re noticing a small Bond theme here, you’re totally right. While Bond got a drop-top, the ’69 Toyota 2000GT was stylish enough without one being offered up from the factory. The elongated front, along with the design in general, makes it feel much more like an Italian roadster than something you would picture purchasing for its “dependable gas mileage.”

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1962 Ferrari 250 GTE

The Ferrari 250 GTE was the sports car for the family man. It was for the guy who wanted a Ferrari but also wanted to get little Timmy to hockey practice with all his gear. As Road & Track said, “A not only grand, but glorious, touring car.” We’d tack on cool as well.

1970 Datsun 240Z

The Jaguar E-Type’s Asian doppelgänger has the same beautiful look as the Jag with perhaps more brains underneath. The thought that went into the car became the hallmark of Japanese sports cars. See, being cool doesn’t just mean looking good (but it mostly means looking good).

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1969 Chevrolet Camaro

It was pretty much a foregone conclusion that this list would include at least one Mustang and one Camaro. What can we say, we like old-school American muscle power. Seeing those white stripes on a blue Z28 just strikes us as quintessentially cool.

Those are our picks, what are yours?


  • Terry Shea

    You’ve got the E-Type pic in the 240Z entry.

  • Terry Shea

    Um…how about a pic of a stock 240Z, not that obscene custom job.

  • http://www.facebook.com/home.php#!/therealNewman Mike Newman

    Our bad on the 240Z pic, just fixed it.

    Also, think the 240z shot we have up now is better (not too much aftermarket stuff).

    Thanks guys!

  • http://cam8510.hubpages.com/ cam8510

    Thumbs up on the 69 Charger.

  • Mr C

    you forgot the gt500 (or 350) mustang

  • Matt

    Fantastic list – big thanks to Cool Material and ArmorAll for pulling together.

    One note: I think it was a serious mistake leaving the Porsche 356 off this list. I’m just sayin..


  • Brian

    What about a GTO?

  • hatrocker

    All others become irrelevant behind the Shelby Cobra. Everything about it screams COOL!

  • Juan

    What about Porsche??… 911 or the classic 356 speedster??…

  • http://none oklacalit

    Seriously people, that’s a 68 charger pictured. The Gen Lee was a 69. 68’s have the round marker lights and the full undivided grill where the 69’s have a divided grill.

  • ernlo

    65 Sunbeam Tiger, it’s fast, rare and a total sleeper.

  • Edsel

    Your “1969” Charger is a 68.

  • http://www.facebook.com/home.php#!/therealNewman Mike Newman

    Good call on the Charger. Fixed it. Thanks for the heads up.

  • Tyler g

    What about the ford gt40!?

  • http://www.heatpumpreviews.org/ Trip

    Sick, I love those cars, great choices, I particularly like the 1969 Ferrari Dino 246 GT. That is a car I want, I have to admit before reading this article I was a A-B guy but this just changed my opinion.

  • Anthonly L

    Defining cool, WOW you took on a tough job. Some of these cars DO define cool, class, elegance, muscle, tough, or fantasy dreams…ghibli, dino, e-type, aaaaahhhhh!

  • Marcus H

    The Ferrari 250 is what I want in my garage

  • Mo

    1967 shelby gt 500?

  • AdmiralJ

    Mike Newman.
    Just wanted to correct what Edsel posted. Your pic is correct on the 69 Charger. The 68 Charger had twin round tail lights on each side. Your showing a 69 Charger. Both are almost identical but for the tail light configuration.

  • Dean S

    At Terry Shea:

    I think you ran across a better a better 1972 246GT in Spartanburg! :):):)

  • John

    3 dubious statements 1) The thing that made the 63 corvette famous was the split window on the hardtop. The roadster is not nearly as significant a model (whether or not it was the 1st year in this run) 2) Referring to the Ghibli as “what the Mazda Miata dreams of becoming as it falls asleep at night.” misses the entire, well known point of the Miata – to look like an Elan, which it clearly daydreams about. The Ghibli is stunning & is arguably what other ugly 8 cyl coupes should aspire to. 3)If one is going to pick “one vehicle that James Bond relied on the most” then it needs to be the one Ian Fleming had him actually choose – the DB4. In the film they settled for the then current DB5 but if you’re going to reference the origin of what makes a Classic car cool, shouldn’t you get it be the actual orign?

  • TJ

    The Pontiac GTO started all the muscle car magic. It IS the definitive cool car bar none!

  • Bob Dopelina

    O my god! Jut fell in love with the 1969 BOSS 429 MUSTANG
    . So great! A must have

  • lee

    that 240 Z is my pride and joy, not only is she good looking but she has a mean attitude, under that hood an LS1,,,,,,,,,,,,,,,,,COOL

  • T

    That 1969 Chevrolet Camaro is really nice I like it