1966 Shelby 427 Cobra

The Cobra series produced by American automotive manufacturer Shelby is one of the most powerful mass produced vehicles of its (or any) era. The 1966 model has so much power in fact, that it goes from 0-100-0 miles per hour in about 14 seconds, undoubtedly cementing its place as one of the coolest car series to come out of the U.S.

1961 Jaguar E Type

You know a car is cool when a competitor car manufacturer calls it “the most beautiful car ever made.” That’s exactly what Enzo Ferrari said of the Jaguar E Type when it released in 1961, and it’s an extremely difficult quote to argue with. It’s one of only three cars to be admitted into the Museum Of Modern Art’s permanent design collection and it was faster than the Ferraris of its time for half the price. What more do you want?

1969 Ferrari Dino 246 GT

What makes this car so cool is the fact that no one expected it to be. It was originally meant to be a “budget,” road-faring vehicle, modeled after the successful Dino series vehicles that preceded it. Heck, Ferrari didn’t even want to put their logo on this car. Of course, as the years passed, drivers began to seek out the Dino 246 GT for its incredibly sleek body and reliable build.

1969 Maserati Ghibli 4.7

When the Ghibli was first unveiled to the public in 1969, the world wasn’t expecting such a rugged body style to come out of Italy given its history of producing cars with natural curves at the time. Nevertheless, the Ghibli sold like hotcakes on the premise of style alone (there were no notably exceptional mechanical specifications to be heard of), but quickly gained a reputation as one of the most reliable cars on the road. Perhaps the Ghibli’s steel body and solid rear axle had something to do with that.

1966 Alfa Romeo Spider Duetto

If you’re a fan of ‘60s movies, you’ve probably seen Dustin Hoffman behind the wheel of this one in “The Graduate.” Otherwise, you may simply feel the overwhelming urge to take an extended road trip while in the presence of this machine. There’s plenty of storage space too, so you can bring as much as you need.

1964 Aston Martin DB5

James Bond wrote the book on cool (okay, technically Ian Fleming wrote the book on James Bond but whatever), and this is the car that the world’s most dangerous man drove. Only 1,063 DB5s were ever made and far less are still on the road today, so if you’re lucky enough (or cool enough) to get your hands on one, you would be wise to hold on tight.

1957 Mercedes 300SL Gullwing

Just look at those doors! Sure, Lamborghini began manufacturing doors that opened vertically on their cars too, but that wasn’t until 1974. This was 1957 and there was NOTHING cooler than opening your car doors like the cockpit of an airplane for your date. Doors aside, the Gullwing was the first car to use direct fuel injection, and has captured several high-profile race victories (Le Mans anyone?) as a result.

1969 Boss 429 Mustang

Style points right off the bat for having “Boss” in its name. It’s a good thing this car is so cool because the engine in this beast is so big that there’s no room for frivolous additions like air conditioning. Trust us when we say you won’t notice when you’re screaming down the highway in this oversized 7.0L semi-hemi powered beauty though.

1966 Lamborghini Miura

The Miura is the granddaddy of all high performance, two-seater sports cars as well as Lamborghini’s flagship vehicle (in its prime, of course) which makes it inarguably cool by default. Besides that, it has a super slick body and a 3929cc V12 engine that is sure to bring a smile to the face of anyone lucky enough to control it — IF you can control it.

1969 Toyota 2000GT

Two words are prevalent here: limited production. A staggeringly low 351 Toyota 2000GTs were ever produced, making this one of the most sought after cars in history. It’s not just the rarity of this vehicle that appeals to gear heads though, this car also represents a significant turning point in the Japanese automotive industry. Before the 2000GT, Japan was mostly known for creating affordable economy vehicles before this baby hit the market.

1963 Corvette Stingray

For automotive enthusiasts worldwide, the original Corvette Stingray stands tall as one of Chevrolet’s most notable achievements (certainly the most notable of the Corvette line). This version of the Corvette is faster and more stylish than any of its predecessors, and while some may argue that several of its successors have experienced stylistic upgrades, something about that “classic cool” element still carries a lot of weight with us.

1969 Dodge Charger

For some reason, Dodge just never got as much recognition for its Charger line as Ford did for their Mustangs. We’re not quite sure why though. The Charger is a quintessential American muscle car and it has just as much under the hood as any of its competitors do. It did get its big break as “The General Lee” on “The Dukes Of Hazard” though and that’s cool enough for us.

1970 Datsun 240Z

Grand tourer or powerful sports car? Well, why not have both? That’s exactly what you get with the Datsun 240Z (although they prefer you call it a “personal” GT car). Datsun put this machine together with quite a bit of forethought and intelligence with the price being a key factor. The end product is a well-balanced, well-thought-out vehicle that captured the attention of adventurous American sports car fans. If you find one of these vehicles for a fair price certainly jump on it!

1962 Ferrari 250 GT/E

Yes, we have a four-seater Ferrari on our list of definitively cool cars. Get over it. This was the first large production four-seat Ferrari ever made and it greatly contributed to the company’s financial success it still enjoys today. Never have you seen such a tough-looking, smooth-driving family car. If that’s not cool, we don’t know what is.

1969 Chevrolet Camaro

Boy, 1969 was one cool year for auto manufacturing, but Chevrolet took the cake with (arguably) the best Camaro ever produced. It’s American muscle, which we love, but it’s also one of the most popular cars among collectors. A list of cars that define cool simply would not be complete without this entry.