“I’m gonna get me a Cadillac too, if it’s the last thing that I do.”—Stray Cats

For almost a century, Cadillac stood as the epitome of a vehicular oxymoron: American Luxury. But for generations, a shiny new Cadillac in the driveway was proof the American dream was a tangible reality. So ubiquitous was the idea of Cadillacs being the best, that it became a part of the lexicon to refer to anything at the top of its field: “The Cadillac of ______.”

Here are seven great examples available right now, from when Cadillac was truly the Cadillac of cars.

ebay/classic-car-studio

1941 Series 62 Convertible

From gangsters like Al Capone to starlets like Jean Harlow (hers a gift from Howard Hughes), seemingly every boldfaced name of the 1930s and '40s was behind the wheel of a big, bulbous Caddy. This stunningly preserved example was a product of none other than Harley Earl, perhaps the most famous American car designer of all time.

ebay/larryhenso

1949 Sedanette Hot Rod

Is this the car Cadillac meant to produce? It most certainly isn’t. Is this chopped and dropped purple beast the perfect example of everything wonderful about the cult of the Hot Rod Caddy? You’re damn right it is.

ebay/memorylaneautobrokers

1957 DeVille

Elvis bought one for his mother. The Stones, Bruce Springsteen, Aretha Franklin, and Joni Mitchell all sang about them. If there’s anything more famous than a Cadillac, it’s a pink Cadillac. The one available here, a 1957 Coupe DeVille wearing its original pink paint, has been spruced up and is ready to put every other car at your diner’s classic cruise-in to shame.

ebay/annapolis_classic

1959 Eldorado Biarritz

Few specific design elements of a car are more famous and more celebrated than the fins of a classic Cadillac. And Caddy fins literally reached their pinnacle in the 1959 model year, being the largest and most pronounced that the brand—or anyone for that matter—would ever produce. While they produced a number of cars that are certified legends, for many this is the Caddilac to have.

ebay/super-sport-motors

1967 Eldorado

The 1967 Eldorado took Cadillac out of the plush, big-finned era and directly into the space age. With razor sharp angles and a futuristic design, this wasn’t just one of the coolest Cadillacs, it was one of the coolest cars designed. Ever. And while I happen to think these look most sinister in black, it’s hard to say no to this crystal firemist-over-houndstooth example.

ebay/classicsllc

1975 Coupe DeVille

Two doors, 20 feet, tufted leather and rides like a cloud. This big long coupe is everything a '70s Cadillac should be. Add the Rolls-Royce style grill, the winged hood ornament, the wire wheels, and the hard-shell spare, and there’s just no other way to put it: This car is king.

ebay/traveler1670

2013 CTS-V

If you’re asking what a two-year-old car is doing in this roundup of the all-time great Cadillacs, it just means you’ve never driven a CTS-V. This is the car that truly announced that Cadillac was back, and in a very big way. A 556 horsepower way to be exact. This is, without a doubt, the greatest American sports sedan ever produced. Perhaps until its 640 hp 2016 replacement hits the showrooms that is. 


John Munson is a contributor to Supercompressor. 

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