Oldsmobile, part of the auto giant, General Motors, first introduced the Oldsmobile 442 as an optional package for the Cutlass and F-85 models made from 1964 to 1968. The 442 would become a car on its own from 1968 to 1971, only to become an option package once again in the mid-1970s.

The Oldsmobile 442 arose from an internal competition between the Oldsmobile and Pontiac divisions of General Motors. Originally, the muscle car was developed in response to the unexpected success of the Pontiac Tempest GTO in 1964.

Since the 1964 model year was more than halfway done by the time the Oldsmobile 442 was ready, the car became the B09 Police Apprehender Pursuit option for the F-85 and the Cutlass. The name, "442" referenced the model's four-barrel carburetor, manual four-speed transmission and dual exhaust.

 The 442 package included a heavy duty drive shaft, wheels and shock absorbers. Buyers could also add on air conditioning, an AM/FM radio, an electronic opener for the trunk and two-speed windshield wipers.

In 1965, Oldsmobile introduced the 442 as a more aggressive package. The new, official definition of "442" became 400 cubic inches, 4-barrel carburetor and two exhausts. The default transmission was a manual three-speed, with the fourth speed as an alternative option. Buyers could also choose a two-speed automatic transmission instead of the manual one.

The 1965 the Oldsmobile body had the "442" label on the dashboard and chrome body side scoops. Both the retractable front seatbelts and the interior console were optional. Models made from 1966 to 1968 would have slight changes, such as three-speed automatic transmission, which was introduced as an option in 1967.

The Oldsmobile 442 became its own car model in 1968. The engines had a bright copper hue with a red air cleaner. These models used newer technology and had more options available than the package predecessors. In 1970, the 442 was overhauled for performance, sporting a sleeker body and using a V-8 engine.

In 1972, muscle car sales began to slow because of gas and insurance price hikes. The 442 went back to being an option for other models, such as the Holiday Coupe. Eventually, the 442 became a limited edition option only and was not available by 1981.