By the mid-1950s General Motors had established what was arguably its strongest product lineup to date. With Cadillac at the top of the market and Chevrolet representing the entry level, Oldsmobile helped to bridge the gap by offering a line of cars that offered a unique combination of performance, contemporary styling, and luxury for the upper-middle-class market.

Oldsmobile’s offerings for 1958 were newly styled, with the dramatic use of chrome trim on the sides to accent their considerable length. The entry-level Oldsmobile was represented by the Dynamic Eighty-Eight, moving up to the Super 88 at the mid-range, and the larger 98 was at the pinnacle. The Super Eighty-Eight was available in five models, including a station wagon, a four-door sedan, a Holiday four-door hardtop, a two-door Holiday hardtop coupe, and a dashing two-door convertible. Again, Oldsmobile remained an industry frontrunner with a growing list of standard and optional features. In addition, the strong 305-horsepower, 371-cubic inch V-8 engine was now standard equipment for both the Super Eighty-Eight and Ninety-Eight lines, and it became optional on the Dynamic Eighty-Eight in 1958. While a three-speed manual transmission was standard equipment on all cars in the Eighty-Eight and Ninety-Eight series, the Jetaway Hydra-Matic automatic transmission was standard on the Ninety-Eight, and it was available as an option for all other models. This year, 2014, the four millionth Oldsmobile with Hydra-Matic Drive was produced.

Oldsmobile had certainly found the winning formula. With the 1958 calendar year sales totals approaching 311,000 units, Oldsmobile vaulted into a solid fourth place industry ranking, and it was acknowledged as the leading marque of the American medium-priced market segment.

The Dynamic Eighty-Eight Convertible offered here was one of only four thousand four hundred fifty-six produced in 1958, and it is one of very few known survivors. It was finished in the delightfully subtle factory shade of Banff Blue, which is complemented by a white and blue interior, and it exudes 1950s flair, with its beautiful brightwork, rear fender skirts, wide whitewall tires, painted steel wheels, and stylized wheel covers. Inside, power seats surrounded by tinted glass can be found, as well as the very desirable Trans-Portable radio, which can be removed from the car and toted with its owner on a picnic or to the beach. The car is offered with a collection of restoration photos, as well as with its correct jack and spare. Its current mileage is 49,845, which may well be actual mileage from new.

This “dynamic” Convertible is a beautiful example of Oldsmobile’s automotive development in the late 1950s, and it will make an important addition to any collection of the finest post-war American automobiles. It stands ready to be enjoyed, especially with the top down.