Same Owner For 53 Years: 1965 Oldsmobile 442

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There is somewhat of a debate that crops up every now and then related to the Olds 4-4-2, that the numbers always define a 4-barrel carburetor, 4-speed manual transmission, and dual exhaust. That would mean that this 1965 Oldsmobile 442 convertible isn’t a real one because it has an automatic. This solid, rust-free example can be found here on craigslist in beautiful Sonoma, California. The seller is asking $9,500 or reasonable offer for this car. Thanks to Ikey H. for sending in this tip!

The Oldsmobile 4-4-2 has had more than one definition throughout the decades, even by Oldsmobile itself. It did start out as defining their new model with a 4-barrel, 4-speed, and 2-exhaust pipes and it was an option that was a mere $285 extra in 1964 ($2,337 today). It was available on both the Cutlass and F-85, but most examples were Cutlass-based. Things changed the next year when the 400 V8 was dropped into the 1965 models thus tweaking the 4-4-2 definition to being a 400 V8, 4-barrel carb, and dual exhausts. On modern cars it would probably stand for 4 heated seats, 4 charging ports, and 2 latte holders.

Despite the surface rust, this 442 looks and sounds like a rock-solid car. The seller says that it has no rust-through and the panels look straight and the frame is as straight as an arrow according to the seller. This is one of those drive-as-you-restore projects and it would be a great one for that. This car is being sold by its second owner who has owned it since 1966! A convertible has to be about the ultimate option for most cars and NADA lists an average retail value for a ’65 442 convertible as being $50,200. Recent sales of nice cars show that to be a fairly accurate number.

Power windows in a 1965 car! Sorry, I got overly-excited there but I rarely see power windows in vehicles of this vintage. The Olds 442 was somewhat of a luxury-muscle car as the Cutlass was a nice model, not a stripped-down economy car. Oldsmobile was already trending (as nobody in 1965 most likely ever said) towards the luxury end of GM’s car family for the last several decades so it shouldn’t be as surprising to see those power windows as it is. You can see that there will be lots of work to do inside but new parts are available as you might expect. I have to admit that a 4-speed manual would have been great to see in this car. I wonder how much more it would be worth?

This isn’t the 330 V8 that first appeared in the 442 in 1964, in 1965 Oldsmobile gave us their 400 cubic-inch V8 which had a very stout 345 hp and 440 ft-lb of torque. The engine looks rough and rusty and this car deserves a proper restoration so it’ll most likely come out for a full rebuild. They say that it was started and driven no less than 5 years ago, but hopefully, it’ll fire up for the next owner. Are there any 1965 Olds 442 fans out there?

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  1. JP

    Had a 69 442 convertible in 1983-86-I would love to have it again.

    Like 1
  2. Will Fox

    Power windows ARE a rare option for the `65 Cutlass models. It was also available in `64, and just as seldom ordered. Believe it or not, the `62 first-year small “Cutlass” package on the F-85 models had them too, as options! While plenty of reproduction parts are available for the more popular `68-72 442’s, I have to wonder what’s around for the `65 models. Upholstery? Door seals? door panel/trim items? I’d have to research that one. Nice solid west-coaster, well worth the expense to restore.

    Like 5
    • Scotty GilbertsonAuthor

      Will, that’s good to hear, I thought that I was maybe making too much about it having power windows. It seems like we sometimes don’t even see them on luxury cars of this era – Cadillacs, Lincolns, Imperials, Olds 98s, etc.

      There are a few reproduction parts available from different companies for the early 442s, I put a link in the 4th paragraph:

      Like 2
    • Robert L Roberge

      I had a ’63 Buick Skylark conv. It had pwr windows as it’s sole option. I wonder if they were favored because of the fact it’s a convert. and it’s way more convenient when going topless.

      Like 1
  3. karl

    Definitely a car worth restoring , but to me the ’65 Cutlass was the weakest of the mid size GM designs for that year – Too “Delmont 88” looking , if you know what I mean . The Skylark, Lemans and Chevelle had such clean lines – but that’s just my opinion ; and I hope it finds a good home !

    Like 5
  4. Todd FitchStaff

    Friends of mine are restoring a ’65 Cutlass convertible (330, manual trans, non 4-4-2) right now. People forget how these hot 3xx cid engines could be before the 400+ cid monsters came in later. Love the power windows, and how the radio and other controls are located conveniently nine feet away in front of the passenger. Had a legitimate guffaw from your “4 heated seats, 4 charging ports, and 2 latte holders.” zinger. Nice one, Scotty.

    Like 10
    • Scott Williams

      My first car was a 65 Cutlass with the 330 4v and Jetaway auto. Lightly optioned and that car was pretty quick to 16 year old me!
      Sold it to a guy who test drove it, then looked at me and asked me if it had a 400 in it…

      Like 3
  5. TomMember

    Wow, what a shame. Same owner for 53 years and this is how they took care (or lack thereof) of it?

    I have a 64 Olds 98 with 58K miles on it. Dad bought it 1 year old in 65. I was born in 66. Still has the plastic on the seats.

    Power windows are a rare options as I have had a few cars of the 60’s with them including the 98, a 67 442 and a 67 Firebird 400 Convertible. HOWEVER, albeit cool & rare, crank windows ALWAYS WORK. Power windows are nice to brag about but a can be a PITA !. (Pain in the …)

    Like 9
    • local_sheriff

      Agree it’s surpricing how awful it looks considering it was almost a new car when they got it.

      Agree with you on the power windows (or power top for that matter)too,I’ve never really understood the point with them. OK, I understand most people will say it’s ‘convenient’ to have them, but I’ll ascertain it’s not particularly CONVENIENT to troubleshoot them in the middle of nowhere and you need them to come up! And don’t expect them to fail on you on a bright shiny day… Though 60s cars wiring harnesses aren’t that complex, there are enough wires there already for most of us

      Like 3
  6. Jim in FL

    Can confirm that it was not unusual to see higher end cars with fewer options in the 60’s. As a kid in the 70’s, mom drove dad’s hand-me-down 66 Bonneville convertible. Top of the line, but no AC or power windows. Did have FM with reverb, though. I think it was more common to order what you wanted and leave out what you didn’t. As someone here said, 389 was no slouch for power either.

    Hydro-e-lectric has a lot of the rubber and convertible bits for these.

    Like 1
  7. John Taylor

    I like it, but with our dollar being more and more like a Paco every day this would cost me nearly $13,600 plus freight etc to get it here, but I think it would be a great project especially if it doesn’t have any rust issues. Just a cool cruiser, but just what I would think strip the whole car down chassis off and do a nice fresh rebuild.

    Like 1
  8. ccrvtt

    Before we go any further – the 1965 Cutlass was not as good-looking as the LeMans, but it was far superior to the Buick & Chevy.

    A friend from high school showed up in my driveway with one of these around 1968. It was dark green and had a column shifted automatic. Some goofball had managed to wedge some L60’s on the back giving the car an awkward rake.

    My mother had a 1965 Vista Cruiser and it was a very nicely trimmed car. Of course it was assembled in Lansing so it was probably a better Oldsmobile than one made in California ;)

    This one deserves a total restoration. Please don’t put 20″ rims and rubber band tires on it.

    Like 6
  9. cold340t

    I remember seeing this car driving 30yrs. ago. Always wondered what happened to it. Hope it gets restored. Glad it’s still with us and not parted out/crushed. Despite the poor condition it’s in now.

    Like 3
  10. Steve

    Aftermarket sheet metal is basically non existent. Rear qtr like to rust out as with the rear bottom of fenders. Mechanically parts are easy and fairly cheap., interior parts are the same way. Front bumpers are not reproduced, front bumpers like to rust out at the mounting points, but used cores are out there.

    Like 1
  11. Rex Kahrs Rex KahrsMember

    Nowadays it’s 4 hipster douchebags with 4 dogs staring at their I phones for 2 long!

    But all seriousness aside, get serious! 10K? As the hipsters would say, LOL, OMG! NOT!

    Like 2
  12. Mike Schnittker

    My Dad bought a 1965 F-85 new, I remember going to the dealer and seeing the Toronado which blew my mind. It was a terrific family car, I later drove it in college in the early 1970’s, could hold half of the world in the trunk!

    Like 0
  13. Dave S

    Had a blue ‘65 Skylark in the early ‘80’s with power windows and a power top. Loved it! Parked it on the wrong side of the street and it got mauled along with two other cars. Bad way to start the day. A guy in school had a red ‘64 442, convert with a black top. That was one really nice car!

    Like 0

    I had a ’67 Cutlass Supreme without the 442 option yet the original owner of the car ordered hers with all the same individual options as the “4-4-2-” designated option. She told me her sales agent at the dealership suggested it as to avoid higher insurance premiums that the normal 442 option(with badging), garnered.

    Like 0
  15. mike D

    HI,, first off… 442 = 4- 400 CI 4+ 4bbl 2_ 2 exhaust one can’t say the 4 is for 4 speed cuz some came with automatics Most likely this was a dealer ordered car to be put on the showroom floor thus all the options it will be indeed a nice looking , nice running car once brought up to par

    Like 0
    • Scott Williams

      For 1964 only, it did mean 4 barrel, 4 speed, and dual exhaust. No slushbox 442s in 1964 (And no 400 engine either).
      The 64s are *very* rare now though.

      Like 2
  16. Pete Phillips

    Go ahead and whine and criticize the car, the styling and the price all you want. This is a blue-chip collectible muscle car that hasn’t been molested. And it’s a convertible, to boot! Go out and find another one this solid and this original at this price. Go ahead, I’ll wait. No matter how much you put into this car, you will get it back when you sell it, and there will be 40 or 50 buyers waiting for it. If I were closer and had the space, this would already be in my garage at the asking price.

    Like 4
  17. CaCarDude

    The ’64 and ’65 “A” body Olds was a nice body style and were superior to the later year models IMO. Also as far as the lineup from GM for ’65 I think the LeMans was top and then Skylark, Olds and finally the boxy Chevelle. I may be a bit prejudiced as I prefer Buick over all the others,.. someone once said that a Skylark is just like a Chevelle but with nicer taillights. This Olds listed deserves a total restoration and hope it gets it as not many of these are seen at shows I have been to.
    As far as Interior you can buy the whole pkg. from Legendary in New York and is actually as good if not better than OEM.

    Like 1
  18. Maestro1

    Read Pete Phillips remarks and keep quiet or buy the car. This has very strong upside and is a joy to drive. Take it down to the bones and do it right and you will get every penny out of it. Meanwhile drive and enjoy. I’m near Sonoma but I have no room. If I did, I’d buy it right now.

    Like 3
  19. C parsons

    There are parts available for this not as much as the 69-72. I have a 64 cutlass from California in primer I’ve had for 30 years I would consider selling with lots of extra parts

    Like 0
  20. jackthemailman(ret)

    My ’66 was 4(00 c.i.), 4 speed transmission, dual(2) exhaust.

    Like 0

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