The 1959 Cadillac will always be in the pantheon of iconic ’50s designs. When I first saw pictures of one, and later saw the actual car in real life (parked at a funeral home, same color and model as this example), I had trouble believing that what I was seeing was real. Yes, it’s the fins–but it’s more than that. It’s the voluptuous size, the “streamlined” looks, the masses of chrome formed into interesting shapes, the thundering yet silky V-8 engine, and the quad taillights that look like flames of fire shooting out the back of a rocket. It is a car that has captured the imagination of millions, which is why you’ll have to pony up a lot of cash to own one–more so than comparable Cadillacs that are a few years older or newer. Which makes this Series 62 sedan, despite its faults, seem like a good value for the 1959 Cadillac lover.
This ’59 Cadillac in Pinehurst Green (original paint) is located in Wingdale NY, about 50 miles north of New York City. It is described thusly:
Let’s get to the good stuff: the seats and upholstery look outstanding…
Excellent original upholstery means a lot to me. It can never be duplicated quite like it was when the car left the factory. Same with…
…the dash pad, which isn’t cracked or warped (as many of them are). Autronic Eye is present.
Just beautiful!
Trunk lid with original jack instructions.
“How many bodies can you fit in there?” That joke is so old…🙄
Under the hood: the 390 cubic inch V-8 engine develops 325 horsepower at 4800 RPM. Everything looks neat, correct, and in place.
OK, there’s some rust. It’s bad, but not too bad. I think it can be dealt with.
Ditto with this surface rust on the trunk lid. I’d like to think that it could be scrubbed and polished out–I’ve done this before with reasonable success. I believe in preserving original paint whenever possible, even if it’s not perfect.
Paint code 30: Pinehurst Green.
Loving the instrument panel, which is in excellent shape. Rather minimalist compared to the chrome-bespangled ’58 instruments. Still a product of its time.
So I think this car has a lot going for it. The $25,000 price (subject to negotiation) is not outrageous for what this car is. Most ’59 Cadillacs that are not basket-cases sell for a lot more. If it were me, I would simply repair things that need attention, clean and polish to make it as cosmetically appealing as I can, and just drive it.
Too many cars of this type that I see at shows are so over-restored and artificial-looking–it is refreshing to see something like this which is so honest and original. It’s the way I remember them.

Since we’re talking Cadillac, I thought I would share my experience owning two 1958 Cadillacs, one year older than our featured car.
The black one (above) I purchased at the Lead East car show held at the Parsippany (NJ) Hilton in 1995. I paid $5500 for it. I always wanted a car from the ’50s, and now I had one. It was a very exciting time for me. I called it “the gothic cathedral” of automobiles, and it boldly stood out from everything else on the road at that time.
When I first drove it, my feeling was, “This thing rides like a train!” You step on the gas and the Cadillac would surge forward–there seemed to be tons in motion (and there were!) This heavy car builds up so much inertia that you have to adjust your driving style a little bit. The brakes, though power assisted, had a rather hard pedal and the brakes were none too powerful. Whoa! Who is the master of whom? On smooth roads the Caddy was very level and solid, as if it were riding on seamless train tracks. You gently guided that big steering wheel as the engine silently purred. Off the boulevard on more challenging surfaces, it felt a little bit squishy and imprecise, but not terrible. Nothing’s perfect, right? You get used to it.

I owned the black Caddy until 2017 when I found the two-toned gray one (identical model) on eBay. My black one now had 133,000 miles, while this gray one had only 79,000 miles and was in much better condition overall. So I bought the gray one for $12,900 and sold the black one for $10,000, which allowed me to recoup much of the money I had spent on it over the years.
A lot of this sounds like sweetness and light (and it often was). But I have discovered some less-than-desirable things about Cadillacs of this vintage. They are more fussy, expensive to run, and trouble-prone than other old cars I have owned. I needed to have the Bendix Treadle-Vac power brake boosters rebuilt several times. Without an electric fuel pump, cold starting is very hard. Electric fuel pumps failed. The carburetor would flood (with or without the electric pump). New water pump. Rebuild radiator. New driveshaft bearing. New exhaust system (duals, twice as expensive). Cracked exhaust manifold. And other things I can’t remember. Plus I was getting maybe 8 MPG in town, maybe 12 on the highway (premium).
All of this fuss and expense was really taking away from the fun. And now new problems were cropping up. So in 2021 I sold the gray ’58 for $14,000 and bought this 1960 Dodge Dart Phoenix for $8000, giving me $6000 to play with. The Dodge was a dull gray (not original paint), so I had it repainted blue and white. It is a Slant Six, with power steering and power brakes.
So surprise, surprise–in my opinion, compared to the ’58 Cadillac, this Dodge rides and handles better. It has comparable engine smoothness, silence and pick-up, and plush seating comfort that meets or exceeds Cadillac! TorqueFlite is smoother and more responsive than Hydra-Matic. The power brakes apply like velvet. I know it’s hard to believe, but it’s true. Plus it has a dramatic styling concept in the space-age ’50s vein, with a unique look all its own.
My 1960 Dodge dashboard.
In 5 years of ownership I’ve had very little trouble with it. I had some brake work done, and I just put in a new electric fuel pump. Other than that, it’s just “turn the key and go.” I’m getting much better fuel economy too–and it’s regular or mid-grade gasoline, not expensive premium.
So I can’t exactly give Cadillac a ringing endorsement because I think other cars are better overall and cost less to buy and maintain. But I’m still a Cadillac fan because they have that certain “special something”, especially this ’59. And I’m thinking that the 1959 Cadillac is a better product functionality-wise than the ’58 because of its mechanical refinements: a revised 4-coil suspension (If it’s anything like the ’59 Chevrolet’s, it will be soft and absorb bumps well, while still feeling “geared to the road.”) There was a new power steering unit (Roto-Matic) which may feel less “gooey” and steer more responsively. The power brake unit was re-designed; maybe it’s more reliable with better brake pedal feel. The only way to find out is to drive a ’59 Cadillac yourself.

Yes, the 1959 Cadillac. It’s a beautiful and inspired machine–and like most of man’s creations, it is an interesting mixture of good and bad features. It will always have a place in my heart despite its imperfections. Who said, “It’s not things themselves that are important, but the emotions they create.” That’s certainly true of the ’59 Cadillac!
Related CC reading:
Curbside Classic: 1959 Cadillac Coupe de Ville–Flamboyant Survivor by Moparlee
Curbside Classic: 1959 Cadillac Coupe deVille–False Prophet Of A New Era by Paul Niedermeyer











































Seeing one of these in the wild now is an extremely dramatic sight! Several years ago I saw one in very original condition, probably a notch or two more worn than this one, in black. I saw it turn into the parking lot of a local Mexican restaurant and two or three couples get out of it. I have seen so many pictures of highly restored ones (often painted red or pink) that seeing an actual one in motion is almost surreal, like you don’t expect something of this shape to actually function like a car.
Like you, I prize original upholstery. This one looks extraordinarily plain for a Cadillac – the original fabric of my 1959 Plymouth Fury (preserved under clear plastic seat covers) looked more ornate. Though this fabric is almost certainly of higher quality.
Also, this 59 is kind of the bookend to the 1963 model I once owned, which I peg as the end of the 1950’s Cadillac driving experience. I remember being amazed that a 5000+ pound car with under 400 cubic inches could be so fast. And I remember the steering on my car as quite good – it drove extremely well in almost all conditions. So I feel like this 59 would probably feel much the same. If I ever get another old car, it will be something smaller and simpler than one of these. But I have to admit that this is one sweet old Caddy.
My dad bought a cream puff used 1960 Cadillac in 1967 with only 20,000 some miles. All the bells and whistles but no AC. Greatest radio ever. Took my driving test in this car. It was easy to park because the fins lined up with the guide posts. Learned to keep it to the right on rural two lane roads. I think my dad liked this car better than any other he owned.
I wonder what the rationale was for GM spraying lacquer instead of enamel on their cars. Seems like it was not very durable.
It is my understanding that lacquer flowed out better after painting and looked better when brand new. Also, imperfections that made it to the dealer would often buff out easily.
I was here to say the same. No amount of polishing and waxing will make that paint shiny in five years or even less.
My father bought a ‘67 Fleetwood either in 1970 or ‘71. It was a lovely car, rode and drove beautifully.
He ended up trading it toward a new ‘72 AMC Ambassador. Reason being that the Caddy was nickel and diming him to death.
It’s always nice to see your Dodge. Even so, I wish it had that crazy clock, which, scaled up, wouldn’t look out of place at a World’s Fair.
Ah, yes–the “Satellite” clock– Here it is in action:
https://youtube.com/shorts/Bm-zENbgAP4?si=2chcycN3qdOuUOZD
Thanks for showing us that, Stephen! Always wondered what it was like in action.
I am not much of a fan of the 1959 Cadillac, or the ’58 that came before it. Both went way too far with chrome, fins and other geegaws. It took until 1961 to return to some semblance of sanity.
I also don’t get the soft ride. I suppose it was comfortable on the interstate, but any kind of rough road would induce undulations and bottoming out. Your Dodge is proof: it doesn’t really ride any worse than the Cadillac and it much more controlled on rough roads.
My first Cadillac was a 1959 Coupe deVille, Starlight Silver, Dover White top, black and white cloth and leather interior. That was in 1966 when I was 19. It was was an extremely sharp car and I paid $850. It turns out today it would have been very wise to have hung on to it !!!
The Dodge dashboard is amazing !
I didn’t like the ’59 Caddies back when, now I think they’re great, look like space ships =8-) .
That turret clock is fantastic, I’ve never seen one before .
-Nate
I own 8 – 1959 Cadillacs, including Eldorado Sevilles. Also own a few ’60 EldSevs. My suggestion: there are tons of these models out there, that is, they’re certainly not rare, particularly SDV’s. Don’t get in a hurry. Wait for a rot-free car to come along, even if you have to spend another $10K…. it’s worth it. If I were you, and you were fine owning a 4-door model, definitely go for the Fleetwood. You only live once, and the Fleetwood epitomized the 1950’s over-the-top design.