Not so long ago, General Motors was able to justify having at least one brand for every day of the week. In postwar America, Oldsmobile lay comfortably in the middle of GM's brand hierarchy as the maker of cars for middle-class folks who enjoyed the latest features but wanted something more reserved than a Cadillac or a Buick. Oldsmobile's dignified customers still appreciated horsepower, as evinced by the famous overhead-valve Rocket V-8 of 1949, but the division's performance image was in decline by the early 1960s. In April 1964, though, just six months after the historic release of the Pontiac GTO, Olds boosted its reputation with its own big-engine package -- the 442 -- for its newly redesigned F-85 series, which shared its platform with the GTO as well as the Chevrolet Chevelle and the Buick Skylark.
Confusingly, the 442 (pronounced "four four two") did not have a 442-cubic-inch engine. Instead, the numerals indicated that the car had a four-barrel carburetor (atop a 330-cubic-inch V-8), a four-speed manual, and dual exhausts. Olds was able to respond quickly to the less civilized GTO, since many of the 442's performance add-ons came from police-spec Oldsmobiles. The $136 package (option code B09) added 20 hp and included an upgraded suspension, redline tires on wider six-inch wheels, a high-lift camshaft, and fender badges. The B09 option could be applied to any F-85 body style other than a station wagon, but no more than ten four-door 442s were built in '64 -- the package almost always adorned one of the many two-doors in Oldsmobile's convoluted mid-size lineup: F-85 Club Coupe, Cutlass Club Coupe, Cutlass Holiday, and Cutlass convertible.
Only 2999 cars received the 442 package in 1964, but demand was high and Olds built about 25,000 units for '65, when 442 models -- now all two-doors -- got a 345-hp, 400-cubic-inch version of the 425 V-8 from Oldsmobile's full-size offerings. The first "4" now referenced the larger engine, as a three-speed manual became the base transmission and a two-speed automatic was also newly available. The 1966 model year saw a redesign and another break from the meaning of the 442 label (although Olds didn't try to redefine it this time), since a triple two-barrel setup, known as Tri-Power in the Pontiac camp, could be enlisted for the V-8's carburetion duty, boosting output from 350 to 360 hp.