The 20 Coolest Classic Cars Ever

Mercedes Benz 300SL

The world’s first supercar was also the first to sport gullwing doors. At the time of production, the Mercedes Benz 300SL was the fastest car in the world, with a top speed of 160 mph. And while that’s been surpassed in the years since, the classic looks of this Merc have made it one of the most iconic autos in history.

Aston Martin DB5

Even non-petrolheads should recognize this one: the Aston Martin DB5, the most famous of all James Bond cars. Agent 007 first took the 143 mph ride – which featured a larger engine and improved transmission over the previous DB4 Series V – for a spin in 1964’s Goldfinger, the year after the car debuted to the public.

Dodge Charger

While the Dodge Charger is a fantastic car in its original form, it’s probably the 1969 second-generation variant that is most well known, thanks to its appearance in The Dukes of Hazzard TV show. The bright orange “General Lee” spent most of the series making wild jumps and stunts, popularizing it with audiences everywhere.

Chevrolet Camaro

While the Chevrolet Camaro has been called a “rush job” by some, it’s difficult to deny that it is nevertheless incredibly cool. First introduced by General Motors in 1966 to compete with the wildly popular Ford Mustang, the 1967 Camaro variant was available in either standard or convertible models.

Ford Mustang Boss 302

The car so good they brought it back, 40 years later. Indeed, the high-performance Boss 302 – designed to bring the Mustang’s engine up to speed with its Camaro rival’s – was revitalised for a second production run in 2012-13, decades after its original release in 1969.

Ferrari 365 “Daytona” GTB/4

Another vintage car popularized by a TV series; you’ll probably recognize the Daytona from Don Johnson’s eminently cool black version in Miami Vice. This beauty’s slick, rounded shell eschewed the angular nature of previous models, resulting in a uniquely iconic – and impressively powerful – car.

MG MGB Roadster

The 1970 model Roadster may not have the biggest engine – particularly in America, where emission standards restricted it further – or the smoothest handling, but what it lacks in power it makes up for in class. It’s also accessible and affordable, with a fair condition version running as low as $8,000.

Jaguar E-Type

Enzo Ferrari once called the Jaguar E-Type “the most beautiful car ever made” – as if it weren’t cool enough already. Yes, so long as you steer clear of any Austin Powers-style Union Jack paint finish, its curvaceous shell is certainly sufficient to cement it as one of the coolest cars of all time – and that’s not even counting its rip-roaring V12 engine.

Ford Mustang Mach 1 428 Cobra Jet

Prior to 1969, the Mustang series had carried the GT moniker, but owing to concerns that this wasn’t promoting the right image for the sporty speed demon, it was replaced by “Mach 1.” Success followed instantly, no doubt partly thanks to the introduction of the seven litre Cobra Jet FE engine.

AC Shelby Cobra 427

Packing Carroll Shelby’s monster 520bhp V8 engine into the British AC Cobra sports car was no mean feat – but in 1966 Ford managed it, and the results blew the minds of gearheads everywhere. Only 23 of this speed machine were ever manufactured, essentially ensuring that it would one day become a legendary vehicle.

Ferrari 250 GTO

This is U.K. car fanatic and TV personality Chris Evans’ dream ride, which could well be an indication that it’s something special. The Ferrari 250 GTO carries a monumental price tag of around $20 million, and it’s no wonder: thought by most to be one of Ferrari’s most gorgeous designs, the 250 GTO enjoyed only a few years on the production line in the 1960s.

Porsche 911

Forget Ferrari, Ford or Jaguar: the Porsche 911 is the original speed demon. Its inaugural 1963 incarnation has been described as “the most recognizable sports car in history” – and not without reason. It may look like a Volkswagen Beetle that’s been sat on, but it’s still a stone-cold classic that oozes charm and has spawned countless versions over the years.

Chevrolet Corvette

The 1963 Sting Ray model of the Corvette was notable for a couple of reasons: as well as representing the first fixed-roof option – all previous models had been convertibles – it also offered an odd split rear window. Complete with rear suspension, it’s a fast, sporty road vehicle that’s rarely been paralleled since.

Lamborghini Miura

An accidental success for Ferruccio Lamborghini, who didn’t like the original design, the Miura blazed a trail for mid-engined layouts for road cars. The 1971 SV model was the last of the Miuras, able to reach 60 mph in just five and a half seconds and with a top speed of 170 mph.

Ford GT40

Here’s something for the trivia fans out there: the GT40 took its name from the car’s height, which – thanks to its low-slung body – is a mere 40 inches. The super speedy vehicle was originally designed in 1964 to beat Ferrari at Le Mans, and it didn’t disappoint. With four consecutive victories from 1966 to ’69, it doesn’t get much cooler than this.

Alfa Romeo 33 Stradale

Another benchmark for automotive construction, the street-legal Stradale variant of Alfa’s Tipo 33 sports prototype is widely considered to be the first car to have sported butterfly doors. Only 18 such vehicles were produced, between 1967 and 1969, making this stunning car ultra-rare and ultra-expensive.

Porsche 550

The Porsche 550: a racing car unfortunately made famous by actor James Dean, who was driving his own version – nicknamed “Little Bastard” – when he was killed in a crash in 1955. Nevertheless, it’s an exceptionally cool-looking ride and was uniquely versatile for a racing car in that it could also be driven to and from the track.

Jaguar XJ13

Proving to be something of a middle ground between the D-type and E-type Jaguars, the XJ13 has a smooth shell that is truly unique – as only one was ever manufactured. Originally designed to compete at Le Mans, the car never in fact raced, and has never been sold either, with a $10 million bid having been turned down in 1996.

Ferrari Dino

More affordable than the manufacturer’s previous offerings, the Dino was the first mid-engined road Ferrari. And while it may have sacrificed power to achieve that, with a V6 engine in place of the usual V12, it certainly didn’t skimp on stylishness.

Pontiac GTO “The Judge”

In 1969 a new version of the Pontiac GTO – which had itself won Car of the Year two years prior – was introduced; it was nicknamed the “Judge” after a comedy routine on a popular TV show. A muscle car trendsetter, the 1970 GTO Judge’s feature color may have officially been called “Orbit Orange,” but to everyone else it was a striking canary yellow. And it rocks.

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