We might have passed the Summer Solstice, but that doesn’t mean that there aren’t plenty of opportunities remaining to enjoy the sun from behind the wheel of a classic Convertible before Winter arrives. This 1969 Oldsmobile 442 could be an excellent candidate for such enjoyable activities. It presents extremely well, and its engine bay houses a freshly rebuilt 400ci V8 that is barely broken in. I must say a big thank you to Barn Finder Curvette for spotting the Olds listed here on eBay in Willowbrook, Illinois. The seller set their BIN at $53,600 with the option to make an offer.
Oldsmobile released its Second Generation 442 in 1968, marking a brief four-model-year period during which the badge would enjoy standalone model status. The latest offering followed emerging industry trends, featuring styling that was more “sculpted” than its predecessors. Our feature Convertible rolled off the line in 1969, presenting beautifully in Crimson with a power top in contrasting Black. The seller emphasizes that it isn’t a trailer queen, although the sparkling paint and arrow-straight panels ensure this Olds turns heads. Its beauty is more than skin deep. The seller blasted and powdercoated the frame, while the original floors and trunk pan are rock-solid. The top is excellent, as are the trim and chrome. Rounding out the exterior is a sparkling set of new Cragar SS wheels, wrapped in tires from the fine folks at BF Goodrich. That combination may not be original, but it is period-appropriate for this classic.
The beating heart of this Olds is its 400ci V8. The first owner teamed that motor with a three-speed Turbo Hydramatic transmission. This beauty also features power steering, with the seller stating that new items include a 12-bolt Posi rear end and a Wilwood four-wheel power disc brake conversion. The V8 presents superbly, clearly having received a cosmetic refresh during its recent rebuild. It has only clocked around 200 miles since being bolted under the hood, meaning that it should match the 350hp and 440 ft/lbs of torque quoted by Oldsmobile in that year’s Sales Brochure. The motor is barely broken in, suggesting that it should provide decades of reliable service if maintained correctly. The car runs and drives well, and the seller’s claim that it has plenty of power is unsurprising.
The exterior and drivetrain aren’t the only areas to receive updates; this Convertible’s interior also features a few additions. These include a column-mounted tachometer, an underdash gauge cluster, and an AM/FM radio/cassette. The images suggest it originally had air conditioning, but the compressor and other engine bay components are AWOL. The Black vinyl trim is in good condition, with no significant wear. The dash and pad are excellent, as is the console. A few small items exhibit slight wear, but if considered purely as a driver-grade classic, this interior easily passes muster.
Oldsmobile may have joined other iconic marques in the dusty pages of history, but as long as cars like this 1969 Oldsmobile 442 Convertible continue to ply our roads, the brand will never be forgotten. This 442 offers a wonderful blend of style and performance, and with its motor freshly rebuilt, power beneath the right foot shouldn’t be a problem. It isn’t a cheap classic, but the seller’s price is realistic for a Convertible of this caliber. The listing statistics suggest that people like what they see, but do you? If so, would you consider pursuing this beautiful Olds further?
Nice looking car.
Is the 12 bolt a Chevy or Oldsmobile?
Steve R
Looks to be a “Type-O” Olds rear that it would have come from the factory with. 12-bolt cover, 10-bolt guts.
Only thing I would change is the steering wheel to an Olds 4 Spoke Wheel
While I agree the current steering wheel should be replaced, 4-spoke wheels didn’t arrive until the ’70 model year and to me look as out of place as ’70 ram-air hoods on a ’69..
Agreed, you are 100% correct.
Well, what do you know?! There’s a 4-spoke wheel hiding in the trunk.
3 spoke steering wheel is correct I believe…
Nice 442!!
Yes, but not THAT 3-spoke wheel.
The 400 ci was painted red. This is painted gold which would be the 350 ci Rocket unless I am wrong?
50 grand nice? Don’t think so
nice car but the a/c is gone not good especially with a black gut. for that kind of money, it should be 100% and preferably unmodified.
Agreed. Per the cowl tag, It also was originally a Trophy Blue car with white top and Parchment bucket seat interior. Not every muscle car needs to be red over black.
This one is trimmed and painted how this car came from the factory. Correct 3-spoke steering wheel and all. https://bringatrailer.com/listing/1969-oldsmobile-442-56/
i agree poppy. i think there are more red/black cars now than there were when new. i also agree the factory colors were a stunning combo. this will sell nowhere near that other 442 did.
That first pic, reminds me of the Monkee Mobile. I know that was a Barris creation on a 66-67 mash-up GTO but the color, and that angle with the wrinkles in the rag top and chrome Crager SS just gave my memory synapes a jolt!