Cadillac, the Gangsters’ Favorite Car

Imagine yourself behind the wheel: heart pounding, dead of night, roaring through Chicago’s streets. It’s raining, steam rising from the asphalt, and police sirens blare close behind. No, this isn’t the opening of a spy thriller—you’re almost certainly in a Cadillac.

It’s likely 1928 and your name is Al Capone. The most feared criminal of the 1930s owned the first bulletproof car in history. Auctioned in 2012, that very Cadillac sold for a staggering $341,000.

Unlike many automakers, Cadillac’s destiny seemed almost prewritten. Just six years after its 1908 debut, it became part of General Motors—a relationship that endures today. But let’s rewind a bit.

On August 22, 1902, industrialist Henry M. Leland founded the company, naming it after Antoine Laumet de La Mothe, Sieur de Cadillac, the French explorer who in 1701 founded Ville d’Etroit (later Detroit). From its earliest days, Cadillac’s gift for innovation carried it all the way to Hollywood, spawning countless stories involving its celebrity drivers.

Cadillac’s Model A was the first car with electric lighting and a 10-horsepower single-cylinder engine—features that won Britain’s prestigious Dewar Trophy for automotive engineering. But Cadillac’s real revolution was parts interchangeability: mass-producing uniform components so they could be swapped seamlessly from one car to another. The LaSalle, designed by Harley Earl (who went on to become Cadillac’s chief stylist), pioneered this approach.

In 1912 Cadillac won a second Dewar Trophy for its electric starter. Fast-forward to 1957, and the Brougham introduced self-leveling suspension; in 1964, an automatic light sensor turned headlights off in bright conditions; and in 1970, the Eldorado boasted the largest production-car engine ever fitted. Milestones continued with seat belts (1972), the onboard computer (1978), body-contouring seats (1998), and in 1999, the first night-vision camera system and Magnetic Ride Control—an adaptive shock absorber system hailed as one of the greatest automotive inventions of all time.

In 1953 Cadillac unveiled the first Eldorado, widely regarded as the pinnacle of personal luxury cars. Priced at over $7,000—a small fortune then—only 400 were built. Each featured automatic transmission, six-direction power seats, power windows, and, believe it or not, air conditioning. The 1957 Silver Hardtop Brougham convertible offered an automatic folding top and epitomized extra-luxury. With prices starting at $11,000 (up to $14,000 with memory seats), it was perfection on wheels.

Cadillac’s motto was simplicity, yet its clientele were anything but. In 1935, Marlene Dietrich cruised in her Fleetwood Town Cabriolet. Clark Gable—Hollywood’s Rhett Butler—loved his black V16 Fleetwood convertible. Richard Burton spared no expense on his 1956 Series 62 convertible; Rita Hayworth owned one of only two 1953 Ghia-bodied models, now displayed at the Petersen Automotive Museum after meticulous restoration. Sugar Ray Robinson drove a 1959 “Cadillac Rosa.” Nat King Cole, Elvis Presley, and French rocker Johnny Hallyday (in an electric-blue Cadillac) all fell under its spell. From Ronald Reagan to Clint Eastwood, Schwarzenegger to Adam Sandler, Cadillac has remained Hollywood’s favorite car—starring in films from The Matrix to Inferno—and is even a top pick for the fictional gentleman thief, Lupin.