In a move to modernize its lineup, Oldsmobile introduced a completely new 88 in 1961. The full-size car was now 5.5 inches shorter, 3 inches lower, and nearly 4 inches narrower than its predecessor, while utilizing the same 123-inch wheelbase. Impressively, interior room was greater. Looks were all-new, with the wrap-around windshields being replaced by flatter glass with thinner A-pillars. A straight trim piece ran tangentially across the front and rear wheel arches, and a reverse fin accented the lower rear quarter panels.

Under the hood, the prior 371-cid V-8 was replaced by the 98 model’s 394-cid unit, with power now ranging from 250 (on the Dynamic 88) to 325 hp (on the Super 88). The less powerful engine had a low compression ratio, a two-barrel Rochester carburetor, and single exhaust, while the more powerful version made use of a higher compression ratio, a four-barrel Rochester carburetor, and dual exhausts.

As one might expect, body choices ran the gamut. Most buyers opted for either a conventional four-door sedan or a four-door hardtop sedan, though two-door sedans and hardtops, station wagons, and convertibles were also available. The biggest news for 1961, possibly, was the Starfire Super 88 convertible, which was priced at $4,647. The car utilized a center console with floor shift, front bucket seats, an Oldsmobile 98 grille, trim, and wheelcovers, as well as the 98’s 330-hp engine.

For 1962, the 88 series was lightly redone with a new grille, “eye” shaped taillights, and an uptick in power to 260 hp at the low end and 345 hp at the top. The instrument panel was all-new, too. The Starfire became a series of its own, and added a hardtop coupe.

The 1963 cars had fresh exterior styling, including new modern windshields and slab-sided styling with coves in the upper body sides. For 1964, the 88 series expanded to include a lower-priced Jetstar model that utilized the same 330-cid, 230-hp V-8 used in the F-85, as well as a sportier Jetstar I sport coupe. The Dynamic 88 and Super 88 continued similar to the previous year before a full redesign introduced a new generation of Olds 88 in 1965.

Oldsmobile 88s of this period are reliable cars that were often purchased by older buyers who were quite pragmatic. Cars were routinely kept for long periods of time by the original owners, and were well maintained as a result. Olds 88s were often well-equipped as well, making them surprisingly streetable today.