Pontiac established itself as the performance arm of the General Motors empire during the 1960s, releasing what many believe to be the first muscle car in its GTO. Other brands wanted “in” on the action, including Oldsmobile. Its answer was the 442, which enjoys a strong following in the classic world. Our feature 442 emerged in 1966 and is a largely original beast with 88,000 genuine miles on the clock. It presents acceptably as a driver-grade vehicle, but lifting its appearance courtesy of a cosmetic refresh would be straightforward. The Olds is listed here on Craigslist in Southampton, New York. It could be yours for $40,000, and I must say a big thank you to eagle-eyed Barn Finder T.J. for spotting another absolute gem.
The First Generation 442 graced showroom floors from 1964 until 1967. It was essentially an options pack on its more mainstream Cutlass, not receiving standalone model status until 1968. This 1966 model presents reasonably well, with its condition acceptable for a driver-grade classic. The seller confirms it received an older repaint in its original shade of Almond Beige, acknowledging that the quality isn’t great. It would undoubtedly benefit from a repeat performance, although the new owner won’t need to rush their decision. The car is rock-solid, with only a few isolated and minor exterior rust spots. The underside shots confirm it is rock-solid, not suffering the floor or trunk pan issues that often plague these classics. The Black vinyl top is in good order, as are the trim and glass. I doubt the Magnum 500 wheels are original, but they and the redline tires suit this car’s character.
Interior trim in cars of this vintage can show age, and this Oldsmobile is no exception. However, I must qualify that by saying it also isn’t horrendous. The driver’s seat exhibits wear and a couple of splits, which I believe are probably beyond repair. The back seat’s condition is unknown, but it might only require around $450 for a pair of front seatcovers to make a world of difference. The remaining upholstered surfaces look good, and the dash and pad are excellent. I can’t spot any aftermarket additions, and the Hurst shifter provides a hint of muscular purpose.
The performance of the early 442s was hampered by a lack of engine power, with the company forced to utilize its 330ci V8 in 1964. However, the situation soon changed, with the 400ci powerplant joining the party in 1965. Things grew serious in 1966, with two optional versions of the 400 finding their way onto the options list. The W30 is the most powerful and desirable, although the L69 Tri-Power unit occupying this engine bay is no lightweight. It sends 360hp and 440 ft/lbs of torque to a Posi rear end via a four-speed manual transmission. The GTO may have been the king of the muscle cars, but this classic’s ability to generate a 14-second ¼-mile ET proved the 442 was a genuine contender. The seller made a couple of changes to improve safety and reliability, including a front disc brake conversion and a swap to an electronic ignition. Otherwise, the car is original and unmolested. It runs and drives perfectly, making flying in and driving home a viable option for the new owner.
This 1966 Oldsmobile 442 isn’t perfect, and the seller’s price reflects that. The 2023 market correction hit values hard, although there are signs of a rebound. That could make now the ideal time to buy a vehicle like this because it could be a financial winner if values continue climbing. However, some enthusiasts care less about investment potential than driving enjoyment. If you fall into that category, this 442 deserves a close look.
I love how these fine examples of American automotive history continue to roll out of garages, sheds and barns. Even that damn “beautifully ugly”58 Lincoln on here that won’t sell! I love ‘em all!
I like the post roof and plush seats. So few of these seen with the multiple carbs of which this was the last year. Get her out and stretch her legs.
Pretty car! Looks well kept. Love the engine/trans combo. Not crazy about the exterior color but, that’s what you get when your dream car hasn’t been manufactured in almost 60 years. Someone with enough bucks to buy will probably be very happy with this car.
“The GTO may be the king of muscle cars”.
I agree, but what are you trying to do, start World War III??
I disagree, but I’m persuadable. Others may have stronger opinions…
One of the very fastest cars I was ever in was this here, with the 4 speed. In Louisville in ’78 a gent had 2 of these, 4 spds, $400. Each, a lot at the time. Took me for a spin and I remember it very well to this day, 1st gear was we were rear-ended by a bus.
There were old 60’s muscle cars everywhere then but they were all very tired. Not this one.
I bought a ’68 Cougar GT with a 390 and did like it but was not impressive like the Olds 442.
Really like this one.
I had a black one just like this back in the day and it was a quick ride, Loved that car, Wish i woulda kept it!!!
Friend of mine bought one ,red with black top, needed a clutch in maybe 1984 ,500 bucks.
I bought a ’65 when I was working in WV. Mine was a 4 speed car and I liked it. A friend bought a ’66 a week later and I was envious. His was prettier and faster. I like this ’66.
How long ago was that?
I would be hard pressed to decide which body style I liked better, 64/65 or 66/67. They were both quality designs. I appreciated the trim, light look of the 64/65 but also liked the more muscular look of the 66/67. So hard to decide!
That was in 1972
Brian, I distinctly remember your ’65. By the way, did you ever sort out that issue with the rear tires producing all that smoke?
Right number of doors, right number of pedals, and the right number of carburetors. How can you lose?
TRUE diamond in the rough! Sooo rare to find one w/the L69 tri-carbs still intact….& being a sedan w/no console & factory super stock wheels!
What’s NOT to luv’?!
I owned a 67 442 and the only rust was under the vinyl top around the rear window. Big ugly hole that I never knew was there. I loved that car otherwise.
Only qualm I have is the price; it would be in line with a #2 hardtop, but a post coupe that the seller admits isn’t perfect? And there’s no mention of matching numbers. Lower the price to $25k and I might be all over this one like a cheap suit.
Not only is there a mention of matching numbers but there’s also a mention of the T on the heads which goes in line with the three two barrel carburetor setup. It looks 100% legit to me but you’d have to be up there to actually do the research to know for sure.
“Jerry was a race car driver. With 4:11 gears in his 442, he would light em up just for fun.”
Those are not “Magnum 500’s”…they are Olds Super Stock 1’s. Oh yeah, and the L69 3×2 set-up was likely added. If this were a real W-30 car it would be about $100K more. If it’s a numbers-matching 4-speed car though, it is a steal at $40K.
It says right in the ad the tea on the heads means that the three two barrel carburetors came factory. Was a rare option on the 442. You would have to research the van and everything else to make sure it’s accurate but it did happen that way.
Stupid autocorrect. The T on the heads and you would have to research the VIN
This is rare with the L69 option combined with being a sports coupe (post), may have a low gearset but rear gears are never mentioned it seems (a pet peeve of mine).