Long the choice of the Upper Crust, the 149.8-inch wheelbase Fleetwood was known as the 75. The 1959 Fleetwood 75 got its first real redesign since the early 1950s and included the signature big fins. It was available as a nine-passenger sedan or limousine. As might be expected given the hefty starting price of $9,533, only 710 sedans and 690 limousines were built. The chauffeur’s compartment was upholstered in leather, while the rear was Bedford cord, or wool cloth. A division window was standard. The car’s 390-cid V-8 engine produced 325 hp, all of which was necessary to move the model’s 5,500 pounds.

The Fleetwood 75 received the same updates for 1960 as the rest of the Cadillac line, and the more sedate fins suited the car better. A total of 718 nine-passenger sedans were sold at $9,533 and 832 limousines at $9,748.

Many of Cadillac’s big cars went into funeral home service or to wealthy families and were maintained well, but the occasional corporate limousine was often not so lucky when they fell out of fashion. Cadillac Fleetwood 75s prices are relatively affordable today considering their size and degree of luxury. Remember, though, that they are very thirsty and stretch in excess of 20 feet, making their practicality limited. Low production numbers also ensure that trim sourcing will be an adventure, and also that the car will turn heads no matter where it goes.