Cadillacs

Cadillac produced what many considered to be icons of 20th-century automotive design. Although the 1920 Model 59 featured Hollywood style king Harley Earl’s custom coachwork and the powerful V-16 1931 Touring Car was owned by Hollywood starlet Marlene Dietrich and baseball superstar Babe Ruth, it was the Coupe DeVille Series 62 that reestablished Cadillac as the top luxury brand after WWII. Later, the Eldorado’s supersized tail fins because the brand’s signature, prompting jazz great Dizzy Gillespie to pay homage with “Swing Low, Sweet Cadillac.”

Although the late 20th century saw the brand once synonymous with American success become a shell of its former self, the arrival of the Cadillac Escalade spawned a 21st-century comeback. The carmaker began courting a younger generation and the developing world's upwardly mobile middle class with the development of new cars using an “art and science” approach.

Now, a wreathless crest badge is prominently displayed on new models, from the sporty and refined ATS coupe to the ELR plug-in hybrid. And the nameplate is once again a popular luxury option. Everything from pristine old-model Cadillacs to newcomers with high-tech appeal can be found at auction.

Quick Facts

• In the 1920s and '30s, Cadillac's V-16 engines powered limousines that were part of a desert taxi service running between Beirut, Lebanon, and Damascus, Syria
• Vaudeville and classic movie comedian W. C. Fields owned a 1938 V-16 Fleetwood limousine, which he left to his longtime girlfriend, Carlotta Monti
• In 2010, a 1959 Eldorado Biarritz sold at an RM Auction in Culver City, California, for $148,500 while a concurrent event saw a 1930 Cadillac V-16 roadster go for $693,000