Jay Leno Takes an Oldsmobile 442 From a Museum to Memory Lane

Naturally, compared to their modern counterparts, classic muscle cars aren’t quite as fast. But the appeal of vintage cars is about more than just outright speed. It’s why Jay Leno enjoys driving both his ’02 Pontiac Firebird and his 1979 Trans Am. And it’s why he enjoyed being behind the wheel of a museum-loaned 1966 Oldsmobile 442.

‘442’ stands for something significant to Oldsmobile

A black 1966 Oldsmobile 442 in a stone-lined driveway
1966 Oldsmobile 442 | Bring a Trailer

Although Oldsmobile is best-remembered for its luxury offerings, the brand was once “a motorsports powerhouse,” Road & Track reports. However, while it enjoyed great racing success in the ‘40s and ‘50s, by the ‘60s, they were becoming mere memories, Hemmings reports. Luckily, the Pontiac GTO gave Oldsmobile some extra motivation to inject some performance into its lineup, Automobile reports. The result of that was the 1964 Oldsmobile 442.

Often written as ‘4-4-2,’ it was originally an options package for the Oldsmobile Cutlass. However, in 1968 it became its own model, Hagerty reports. And the numbers spelled out exactly what the muscle car offered. But the ‘what’ actually changed throughout production, Hagerty explains.

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In 1964, ‘442’ meant the Oldsmobile 442 had a four-barrel carburetor, a four-speed manual transmission, and two exhausts. However, starting in 1965, the ‘442’ meant a 400-cubic-inch (6.6-liter) V8, a four-barrel carburetor, and two exhausts. But Oldsmobile wasn’t done tweaking the 442.

The Oldsmobile 442 combined performance and luxury

Starting in 1966, the brand offered an optional ‘L69’ engine upgrade for the muscle car. The L69 package swapped the single four-barrel carburetor for three two-barrel carbs, Hagerty explains. And while the L69 option didn’t quite match the 442 W-30’s output, it did provide a noticeable performance boost.

Back in 1964, the Oldsmobile 442 made 310 hp and 355 lb-ft from its 5.4-liter V8, Street Muscle reports. Then in 1965, the muscle car’s 6.6-liter V8 made 345 hp and 440 lb-ft. And thanks to the L69 carb swap, the 1966 Oldsmobile 442 has 360 hp and 440 lb-ft. 1966 was also the first year that Hurst shifters became standard equipment in manual-equipped 442s.

The black-vinyl interior of a black 1966 Oldsmobile 442 with a Hurst shifter
1966 Oldsmobile 442 interior | Bring a Trailer

But the Oldsmobile 442 offered more than just a big engine. Compared to the standard Cutlass, it has bucket seats, wider tires, and “heavy-duty” sway bars, shocks, brakes, suspension, and frame, Hagerty reports. Car and Driver reports that “the 442 was the first of the muscle cars to employ a rear anti-roll bar.” So, not only can the muscle car do burnouts at the drop of a hat, but it actually “handles better than most of its peers,” Automobile reports.

Plus, Oldsmobile didn’t completely lose its luxury image when making the 442. The muscle car offered optional A/C, an AM/FM stereo, power steering and brakes, and a limited-slip differential, Bring a Trailer reports. Later models offered power seats, too, as well as power locks and cruise control. Compared to the contemporary GTO, it’s a more “genteel hot rod,” Automobile reports.

A museum-quality 1966 Oldsmobile 442 takes Jay Leno right back to high school

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Although Jay Leno has a lot of cars, the 1966 Oldsmobile 442 featured in his latest video isn’t his. Rather, it’s on-loan to the Audrain Auto Museum in Rhode Island. The current owner just asked if Jay could “do a little work on it,” Leno says. And while there are a few things left to do, overall, the muscle car is in great shape.

It also comes with some of the previously-mentioned luxury features, like the A/C, power steering, and power brakes. Jay Leno likens it to the Bentley Continental GT since it’s sporty but also big, luxurious, and comfortable. And once those secondary barrels open up, “boy this thing really takes off,” he says.

The rear 3/4 view of a black 1966 Oldsmobile 442 parked on a stone-lined driveway by some trees
1966 Oldsmobile 442 rear 3/4 | Bring a Trailer

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Jay Leno admits that part of the reason he thinks the Oldsmobile 442 is fun to drive might be because it reminds him of high school. “It was just made of unobtanium” back then, he says. Plus, 1966 is one of his favorite years, because car designs weren’t yet affected by crash regulations. But regardless of the reason, he enjoys driving it.

Back in the ‘60s, a four-speed manual was often an optional upgrade for performance cars. A Hurst shifter was even rarer. And in this 1966 Oldsmobile 442 it shifts rather nicely, Jay Leno reports. Plus, that V8 is so torquey, you don’t really need a tachometer to time shifts or need to be in a low gear to pass someone. Overall, the 442 makes for a great classic cruiser.

These luxury muscle cars aren’t terribly expensive

The ‘442’ name appeared on several other Oldsmobile Cutlasses, including the 1990 Cutlass Calais Quad 442. However, while that car was genuinely quick for its time, by this point, the ‘442’ package was “more show than go,” Automobile reports. As a result, the original 1964-1972 442s are the most desirable, especially the 1968-1972 W30 ones, Hagerty reports.

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But, while pristine examples can get pricey, the Oldsmobile 442 is a bit over-looked compared to its contemporaries. You can find decent examples on Bring a Trailer for $20,000-$40,000. And even the museum-quality example in the Jay Leno video sold for less than $80,000.

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