Cadillac’s influential Sixty Special launched in 1938 as a replacement for the Series 65, filling a sizeable gap between entry-level Series 60 models and the larger, more luxurious Series 70. Notable for both its style—the work of a young Bill Mitchell, under Design Chief Harley Earl—and substance, the Series 60 was a showcase of innovations for the brand. A major redesign for 1942 set a precedent that persisted through its final year of production in 1993: Growing a full seven inches in length and one inch lower, the Sixty Special became Cadillac’s longest non-limousine model, outfitted with every amenity and bountiful legroom.

Subsequent redesigns continued to dazzle with the latest styles from the talented Bill Mitchell. For 1957, the Sixty Special Fleetwood adopted sleek “pillarless” four-door hardtop bodywork introduced the year prior on the Sedan DeVille. It also swapped the model’s trademark chromed fender louvers for expansive, ribbed metal panels on its flanks—part of a jaunty rear-end treatment rife with Jet Age inspiration, from the exhaust-nozzle bumper protrusions to towering, chrome-topped tailfins. Pricey and popular as ever, this would prove the best-selling model in Sixty Special history. The design persisted one more year, with 1958’s glitzy model seeing about half the sales of its predecessor as a recession hammered Detroit.

This 1958 Cadillac Sixty Special Fleetwood was previously part of the noted collection of Glenn Boyd and is an exemplary specimen, retaining its factory-correct finishes and numbers-matching engine. A copy of its build sheet on file confirms the car was originally finished as it is today, in Black over Special Sixty-exclusive Silver and Black Calcutta cloth with White leather. Standard equipment included power steering, brakes, and windows, fore-and-aft power front seat, Hydra-Matic automatic transmission, and a burly 365-cubic-inch V-8 engine. Optional equipment included a six-way power front seat adjuster, Basic Group B, consisting of whitewall tires, heater, and radio, and Equipment Group 3, featuring Autronic Eye, fog lamps, door guards, and two license plate frames.

Presented in well-preserved condition with the engine bay showing signs of use, this jaunty Jet Age masterpiece will delight equally at events as much as on the road.