The 1964 Aston Martin DB5 is considered one of the coolest cars of all time.

The 1964 Aston Martin DB5 is considered one of the coolest cars of all time.

Some cars just ooze cool, especially those with a high price tag, sexy good looks and the “right” people driving them.

Here are four of the coolest classics of all time along with the film and music legends who drove them and pushed their cool factor over the top:1. 1964 Aston Martin DB5

James Bond’s long-standing association with this iconic British GT began in 1964, in Goldfinger. “You’ll be using this Aston Martin DB5, with modifications.” (Remember that?)

Whether you love the gadgets like the machine guns and ejector seat or you’re just a fan of its classic Italian styling by Touring Superleggera and chrome wire wheels, the DB5 has more cool in the air of its tires than the entire first season of Mad Men.

2. 1955 Porsche 550 Spyder

James Dean was a budding race car driver of some talent. He ordered what was then Porsche’s fastest dual-purpose (race/street) car available, and after wrapping Giant, had famed customizer Dean Jeffries paint in script on the car the words “Little Bastard.”

Whether that was a reference to the car itself or a reference made to Dean by studio head Jack Warner isn’t clear.

What is clear is that Dean tragically perished in the car on his way to a race in Salinas, Calif., at the age of 24, remaining forever young and sparing fans from a Brando-esque decline.  Dean and the 550 were the originators of the cool ethos “live fast, die young and leave a good-looking corpse.”

3. 1968 Ford Mustang GT 390

Combine a Highland Green 1968 Mustang GT 390 Fastback, Steve “The King of Cool” McQueen and Bullitt, which contains perhaps the greatest chase scene ever committed to celluloid – it just doesn’t get any cooler than this.

4. 1957 Continental Mark II

The Continental MK II of 1956-57 wasn’t branded a Lincoln. Continental was a division unto itself for those years, and to this day it remains America’s best attempt at building a car of Rolls-Royce or Bentley calibre.

At 10 grand, it was double the cost of the average Cadillac and so much hand labor went into the car that Ford estimates they lost $1,000 on each one. The Mark II’s spot in the iconography of cool comes from its association with the Rat Pack during its Vegas/Palm Springs glory years.

Rob Sass is the vice-president of content for Hagerty Insurance. Hagerty is the world’s leading specialist provider of classic car and boat insurance. Learn more at

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