12 of the Classiest Cadillacs Ever Made

The first Cadillac — named for the French explorer who founded Detroit — was built in 1902 on an experimental chassis left over from Henry Ford's second failed company, married with a single-cylinder engine from the recently founded Oldsmobile company, and an American icon was born. The stunning luxury car was an instant hit with the Gilded Age elite. Henry Ford took full control in 1904 and in 1909, and the newly formed General Motors bought the Cadillac Automobile Co. for $4.5 million. Here's a look at some of its most memorable models over the years.

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Cadillac changed the game in 1930 and launched itself past Packard as the preferred luxury brand of America's elite with the debut of the V16 at the New York Auto Show. Although Bugatti had experimented with the concept, the V16, as the name implies, was the world's first true 16-cylinder car. It was also groundbreaking as the first "styled" engine, which concealed all the wiring and sparkled with polished porcelain and aluminum. It cost 10 times as much as a standard Chevy convertible, but stood out as the pinnacle of one of the most exciting eras in automotive history. The V16 embodied the power, elegance, and ingenuity of design that would come to embody the brand.

A Cadillac like literally no other sold in February 2012 for just shy of $1 million at a Sotheby's auction: one built in the 1980s from scratch by renowned craftsman and restorer Fran Roxason from original blueprints and sketches for a 1937 Style 5859 Custom Phaeton that was imagined and planned but never produced. Assembled on a low-mileage 1937 seven-passenger Series 90 limousine, Roxas' Phaeton won first in class at Pebble Beach.

The vaunted Cadillac Eldorado model would later stand on the shoulders of its predecessor, the Series 62. The entry-level replacement to the Series 61 was unveiled in 1940 — the last year running boards and side-mounted spares were available — as a coupe, sedan, and convertible. The C-body gives it a classic torpedo shape, merging a 1930s elegance that was on its way out and a 1940s feel of modernization that was about to arrive.

If you've ever seen an old gangster movie, you've almost certainly seen a Series 70 Cadillac. Of its entire run from the 1930s to the 1980s, though, the peak might have come with the 1946 Fleetwood Series 75. This massive, V8-powered beauty was one of the first luxury cars built in large numbers during the postwar boom. Cadillac cars were back in full production once the company was no longer committed to cranking out M24 tanks for the military, a service Cadillac leveraged for its postwar "battle-tested" marketing campaign. The '46 Fleetwood stoked Cadillac fever in an era when war-fatigued and newly wealthy Americans were thirsty for the finer things. Only 28,144 were ever built, leaving around 96,000 orders unfulfilled for the year.

It's just wrong to talk about Cadillacs without mentioning the 1953 Eldorado. The Eldorado nameplate ran uninterrupted for 10 generations, from 1952 to the early 2000s, and it all started with the '53. The Eldorado was the most expensive car Cadillac made at the time, and it would remain the top of the line or very close to it for decades. Massively powerful, its 331-CI V8 engine roared and its 12-volt electrical system and standard air conditioning epitomized early '50s luxury. Not only is it undeniably elegant, but it's rare — only 532 were ever made of this convertible-only, top-of-the-line version of the Series 62 model.

A four-door sedan that cost more than a Ferrari or a Rolls-Royce ($13,974, or $125,704 in today's dollars), the '57 Cadillac Eldorado Brougham defined postwar opulence and Cadillac luxury and style — it just might be the finest Caddy ever built. It's also one of the rarest — only 740 "Eldo Bros" were ever produced. Fully disappearing side windows, rear-hinged back doors, a brushed steel roof, quad headlights, and a whole heap of 1930s throwback features were all part of the elegant package.

The de Ville Series broke off from Series 62 to become its own model in 1959, and whether you're a fan of the Sedan de Ville or the more famous Coupe de Ville, the long, sleek, sharply curved 1959 model year will always be associated with one word: tail fins. Cadillac introduced them the decade prior, but they peaked — literally and figuratively — with the '59 model, on which they terminated in bullet taillights. The 325-horsepower beast sold more than 53,000 units during its debut year, though in 1960 the de Villes were tamped down; the tail fins remained, but they would never be as outrageous.

Related: Tail Fins and Other Vintage Car Design Features You Don't See Anymore

The designations of "Sixty Special," "Fleetwood," and "Brougham" date back to 1925, when Cadillac began offering Fleetwood-built bodies on its very finest cars, and "Sixty Special" is an homage to models from the late 1930s. All those concepts gelled with the arrival of the 1965 Cadillac Fleetwood Sixty Special Brougham. A four-door sedan version of the high-end Eldorado convertible, which joined the exclusive Sixty Special club in 1963 — most other Caddies bodied by Fleetwood were limousines — the '65 Fleetwood Sixty Special Brougham was, essentially, a yacht on wheels.

No, that's not an El Camino. It's a Mirage, one of the rarest Cadillacs ever made — only around 200 were produced and only between 1975-76. Chevy, of course, produced the most famous and enduring sedan-based light pickup in history, but the Mirage sold to a different crowd. The Mirage had every cubic inch of the de Ville's 500CI V8 engine, and the first one ever sold was bought by none other than stunt driver Evel Knievel. The Mirage was a third-party customization sold through traditional Caddy dealers, but no one can question its importance in the Cadillac legacy; it's the direct forebear of a segment-leading Cadillac that would emerge 24 years later to redefine the brand and serve as the poster child for luxury full-size SUVs: the Escalade.

On April 22, 1976, the "last American convertible" rolled off the assembly line. It was a white Cadillac Fleetwood Eldorado, one of 200 identical collectors edition cars — all with special Michigan plates — built to signify the end of an era. Detroit's auto industry had announced in a collective press release that, like the running boards and rumble seats of old, convertible tops were being phased out as a trend that had passed. Detroit brass, of course, proved to be wrong, but the '76 Eldorado Fleetwood remains a soft-top for the ages, sporting white bodies with white tops, white wheel covers, white leather seats with red piping and, fittingly for the U.S. Bicentennial, red, white, and blue stripes on the hood.

The Seville series ran from 1975 to 2004 and was the highest-priced Cadillac sedan for virtually its entire run. In 1980, its pinnacle emerged in the form of the sleek and swooping Seville Elegante, — the word "elegant" is right there in the name, even if not everyone appreciated the look. The European-inspired interior, French curve, velvety leather and carpeting, and suite of cutting-edge technology were all standard, taking the quality associated with Seville to a new level.

In 1999, Cadillac was still building fantastic cars, but the brand was no longer associated with the world's rich, famous, and elite. That changed when the company roared into the exploding SUV market with a beast of a vehicle that made Cadillac luxury hip again: the Escalade. By then, Lexus and Mercedes-Benz had emerged as the standouts in the luxury SUV market, along with Ford's Lincoln Navigator, but the arrival of the hulking but elegant Escalade quickly became a must-have accessory for movie stars, athletes, rock stars, and other pop culture trendsetters. The Escalade revitalized the brand, sent sales soaring, and introduced Cadillac to an entirely new generation of cult loyalists.