The Coolest Cadillacs Of All Time

Car Culture / 43 Comments

Some Cadillacs are simply cooler than others.

Cadillac has given the world some amazing things, including the layout of car controls as we know them today, the first reliable V8 engine in a production car, as well as the first V16. Cadillac was also the first car company to hire an automotive stylist.

Cadillacs have always had an air of cool about them, and that has led to some legendary celebrities driving them including, Clark Gable, Clint Eastwood, Gene Autry, Elvis Presley, and Marvin Gaye. But, some Cadillacs are cooler than others. Here are nine that we think are head and shoulders above the rest.


Singer, songwriter, guitarist, and all-around legend from the band ZZ Top almost single-handedly brought hot rodding back from the brink of extinction by featuring his own chopped 1933 Ford Eliminator on an album cover in the 1980s. Gibbons has never stopped loving hot rods and has a few Cadillacs under his belt as well. His second most famous car is another icon called CadZZilla, a Cadillac Series 62 Sedanette built by the late hot rod legend Boyd Coddington in the 1980s.

The Cadillac's chopped and flowing roofline is so unique that a windshield had to be specially made to fit, and the fully blended rear quarters are so beautiful it almost brings a tear to the eye. Underneath, CadZZilla burbles away with a 5.0-liter Cadillac V8 fitted with custom headers. And, best of all, Gibbons still loves to drive it.

Supercharged 1953 Eldorado

John Edwards Alexander was a Navy pilot in World War 1 before working his way up the ranks of his family's paper mill company to become president of the company. He also knew Frank Burrell, a test engineer at Cadillac that specialized in making engines produce more power. Alexander wanted a Cadillac, and he wanted Burell to supercharge it. He also wanted the exhaust pipes to be visible and dump their emissions out ahead of the doors like an airplane.

His '53 Eldorado was fitted with a 4-71 Roots-type supercharger from a GM diesel engine and fitted to a beefed-up Hydra-Matic transmission. The exhaust is synchronized with the exhaust pulses and Burrell fitted a bypass valve so the driver had the choice of the big, loud, V8 rhythm and burble or to have the system run underneath the car normally.

1941 Cadillac Custom Limousine “The Duchess"

Edward VIII was the King of Great Britain, Ireland and all the other titles that came with it. However, he abdicated his throne in 1936 to marry an American socialite from Baltimore. By abdicating his throne, Edward became "simply" the Duke of Windsor and began a career of international jet-setting. The Duke of Windsor became a purveyor of style and his influence still rings through the decades as men tie their neckties in a Windsor knot.

Rolls-Royce was going strong at the time but the Duke of Windsor wanted a Cadillac, and not just any Cadillac. His was a one-of-a-kind coachbuilt wonder with each body panel crafted by hand, and none matching any other Cadillac in existence. That carries through the entire car with ornate style and individuality down to the monogram and motifs. Then, to top it all off, the iconic Goddess hood ornament is gold plated.

Cadillac Ciel

It wouldn't be right to not mention one of Cadillac's wonderful concepts, and this one nearly got greenlit for production in 2011. The Ciel, French for sky and pronounced C-L, would have been a low-volume and high-end four-seat convertible. It was even powered by a Direct Injection twin-turbocharged V6 engine paired with a hybrid system using lithium-ion battery technology. At the time, insiders told Automotive news that it didn't have enough brand appeal to justify the investment. We think that's a crying shame because it's gorgeous, and at Pebble Beach Concours d'Elegance that year it blew a lot of people away.


Cadillac Series 452

This was actually a production Cadillac that was first built in 1930 and came standard with a 16-cylinder engine making 165 horsepower. Cadillac only sold 4,400 of the Series 452 (also simply called "Sixteen") models and money was lost on every single one of them over its 10 years and two-generation run, but making money was clearly not the point. At the time, few manufacturers were building V12 engines, and the V16 was an enormous achievement in the cylinder wars of the 1920s.

The United States Presidential State Car

Cadillac's long relationship with US presidents hit its peak in 2013 when GM was awarded the contract for the president's three new limousines. Also known as The Beast, First Car, and our favorite, Cadillac One, there isn't a public specification list for security reasons, but we do know it's bulletproof and so heavy it has to run on truck tires. Rumor has it that Cadillac One has several security spy-movie level features inside as well as a self-contained oxygen supply and a backup supply of the president's blood in case things go really wrong.

MotorAuthority Evan Vucci, AP

Hennessey CTS-V

Hennessy Performance is legendary for building monster horsepower versions of already fast cars, and its 1000- horsepower CTS-V is no exception. Getting an extra 340 horses from the supercharged 6.2-liter V8 isn't straightforward, but Hennessey has mastered the art and one of its CTS-V models will hit 0 to 60 mph in a scorching 2.9 seconds. It's also an excellent way to give the CTS-V a send-off at the end off its 15-year production run.

Of course, if something a bit bigger is more to your taste, Hennessey will dial your Escalade up to 11 as well.

Hennessey Performance Hennessey Performance Hennessey Performance Hennessey Performance

Al Capone’s Model 341

Does it get any cooler than an Al Capone owned Cadillac? Well, the four-door and five-passenger spec is not the most desirable version of the Model 341 to collectors. However, this one was actually owned by Al Capone, and due to its inch-thick bulletproof glass and flip-down bulletproof backlite, it's also one of the earliest known armored sedans. As a result, it sold in 2012 for $341,000.

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