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Excess or Success? 1959 Cadillac Fleetwood Sixty Special

In the 1950s the American public was under the spell of the space race. To indulge this obsession, auto designers saturated cars with jet turbine shapes -repeated in fronts, interiors, and rears. Customers also sought luxury in a way that hadn’t happened before: chrome, gadgets, and power became more accessible to the average driver as Americans became wealthier. An epitome of the style of the day, here on eBay is a 1959 Cadillac Fleetwood Sixty Special for sale, bid to $50,100. The car is located in Austin, Texas, and we have T.J. to thank for this swanky tip! You need a cheat sheet to figure out the 1950s Cadillac species: there were fourteen Cadillac versions within four different model categories. As it turns out, the Sixty Special was right near the top of the heap, exceeded only by the Fleetwood 75 Sedan with its massively long wheelbase.

Faults on this car are nearly nonexistent. The engine bay could be spiffier, but that’s just time and elbow grease. Meanwhile the 390 cu. in. V8 matched with the Hydramatic automatic transmission generated 325 bhp and took the car from zero to sixty in about ten seconds. The seller has rebuilt the carburetor and the brakes; installed new points, cap, coil, rotor, and condenser; and rebuilt the original fuel pump, along with attending to other mechanical items.  The car rides on new tires installed on rare Kelsey Hayes alloy wheels. The original steel wheels and hubcaps come with the car.

The interior is in superb original condition with leather and cloth seats. The Hampton Green color was a special order color (“SO” on the VIN tag). Barely seen in this photo is the Autronic Eye, a period accessory that automatically dims the brights when required – and sometimes when not required! The Autronic Eye could be tricked by reflective signs, rain, and other ordinary phenomena.

The underside is less glamorous; I might spend some time down here to see if a good cleansing would bring improvement – because it’s so fun to get dirt in your eyes. While we’re talking about cleaning, note the grille detail, which is repeated front and back. It’s spotless. The new owner will be charged with keeping it that way. And, while we’re on the topic of the grille, the gas cap is hidden behind a rotating portion of the rear grille, which you can see if you squint. Ok, I can’t close without mentioning those FINS! I am a fin fan, and these are so satisfying. With all these advantages, I think this price has a ways to go. What do you think this car should sell for?


  1. bobhess bobhess Member

    My ex mother in law bought one of these for only one reason… trunk was big enough to hold her outboard motor and all the fishing gear. Need to carry a lunch to get from the front to the back. Well preserved and probably worth the bid at this point.

    Like 19
  2. RayT Member

    Years ago, I had several long talks with one of the GM designers who worked on the ’59 Cads. There’s a fascinating story behind them. While his preference was for the cleaner ’61s, he admitted that the ’59s did exactly what the Chief of Design wanted them to do. Fins and flash pretty much peaked that year….

    Never got to drive a sedan, though I did put some miles on a convertible. It was big. No, make that HUGE. But it was also comfy, smooth, and a real attention-grabber.

    A great car. All it needs is a Lava Lamp.

    Like 22
  3. Rex Kahrs Member

    If you have any doubt how universal the ’59 Cadillac’s appeal is, look at this photo, taken today, as I attended a car show in Croxley about an hour north of London.

    Like 35
    • normadesmond

      How could that not attract attention in the UK?

      Like 12
    • Angel_Cadillac_Diva Angel_Cadillac_Diva Member

      Rex, what is with the chrome skirts?
      And the amber taillights? Are those completely rewired? My aunt next door had a Coupe de Ville and all 4 bullet lights worked for running, stop and blinkers. This looks like the 2 inner do that and the 2 outer are for blinkers.

      Like 5
      • Rex Kahrs Member

        Hi Angel. The Brits use amber lights for the directional signals, so somehow this guy found amber bullet lenses for his ’59 Caddie. Not sure about the chrome skirts, maybe just a one-off thing by a previous owner?

        I was into the Volvo 1800s pretty heavily, and the US tail lenses were red/red. The Euro versions were amber/red. The Americans coveted the amber/red lenses, and the Euros wanted the red/red version.

        Like 15
      • Bill McCoskey Bill McCoskey Member


        Good spotting those lenses. Yes, European specifications require amber turn signals, separate from the red stop/tail lenses WHEN POSSIBLE. Some UK and European insurance companies do give discounts for retrofitting amber lights on the rear. I guess the people reproducing these Caddy lenses also make them in amber.

        In 1987 I imported a 1964 Bentley S-3 sedan from England. It had amber rear lights, and because the car wasn’t yet 25 years old, to get it thru state inspection I had to buy a very expensive pair of rear taillights that were all red!

        As for the chrome skirts [or “spats” in UK speak], no ’59 caddy left the factory wearing them. Somewhere down the line of ownership they were chromed. [Not my style!]

        I had a ’59 Eldorado Biarritz convertible in the same color scheme, but my Eldo had factory bucket seats and red fender skirts! Sold it in the early 1990s, and I still miss it today!

        Like 4
    • Melton Mooney

      …but there is literally nobody looking at it.

      Like 11
    • Kelly MacGregor

      Like the father’s car in the legendary British TV comedy “As Time Goes By”. Missing the cow-horns; but close.

      Like 3
    • Steve

      How did 50s Caddies navigate those narrow English roads?

      Like 6
      • Bill McCoskey Bill McCoskey Member

        “How did 50s Caddies navigate those narrow English roads?”

        Very carefully, especially when driving down single lane country roads, with high berms or hedgerows on each side. And of course Brits are notorious for driving down these country lanes at 50mph or more! All the time I’m thinking “keep left, keep left.”

        When I lived in central Germany in the mid 1950s, my everyday car was a 1956 Imperial sedan, and I can remember the time I got stuck in downtown Heidelberg, and needed the local police to escort me out using a pedestrian-only road. They were happy to lend a hand.

        Like 4
  4. Cadmanls Member

    My grandfather owned one of these when I was young believe it was in 1960 it took the road trip. We drove to Miami Fl from Cleveland Oh, my grandparents, my mother and younger sister all loaded in, his was white with a light brown leather interior. Some things you don’t forget, as I remember his had some fold down rear foot rests. Quite a car, he was a Caddy guy till the early seventies. Quality fell off and he went Lincoln. Anyway the car later went to my uncle and was painted beige. Maybe a year later fuel line or something failed and caught fire. Went for scrap after that. Always will remember that road trip and this was before interstate travel. That Fleetwood was huge, just fit in his garage.

    Like 14
    • panther1000

      If it had the rear foot rests, it would also have the rear fold out extra seats, which makes it a Series 75 Fleetwood (aka 1959 ‘limo’).

      Like 3
      • Bill McCoskey Bill McCoskey Member


        While you are basically [and likely] correct, Cadillac did off a 6 passenger sedan [with or without the division window] on the Fleetwood 75 chassis, sans the jump seats, however only a few were made each year. While this was always an option, it rarely made it to the factory brochures.

        I first discovered these 6 passenger LWB GM cars existed when I found [and bought] a 1941 Buick Limited LWB limo without jump seats [this was the same body as used in the Cadillac series 75]. I also remember seeing a 1957 or ’58 Cadillac 75 LWB sedan at a car show about 10 years ago, again without jump seats from the factory.

        With my Buick, I found that unlike those with jump seats where each seat base was recessed into a lower section of the floor [so the main floor would be flat when the seats were folded up], the Buick had a completely flat floor as part of the body shell.

        Like 1
  5. angliagt angliagt Member

    That thing looks longer than my old ’60 Chevy 1 ton Apache-
    panel truck (it was 20′ long).Could probably put my Midget in the
    A while back,in our neighborhood,I saw a nice deep red
    ’59 going the other way.That thing was HUGE!
    This is the kind of car you want your Dad/Uncle to own –
    you get to drive it (& put gas in it),but get to return it afterwards.
    That way,they do the maintenence on it,& store it.

    Like 6
  6. Bob_in_TN Bob_in_TN Member

    What a unique time and “feel” for the US when this car was designed and manufactured. And it shows.

    Take a look at the ebay ad, it’s spectacular. As is the car.

    Like 14
    • bill tebbutt

      Jewelry. Interstate jewelry..

      Like 15
      • GitterDunn

        “Interstate jewelry” – I like that!

        Like 5
    • Jay E. Member

      I agree. I kept hoping for more photos and the ad delivered. The photography is amazing. The car is stunning. I cant believe this isn’t a 6 figure car.

      Like 10
  7. tom Crum

    I used to have a stretch Cadillac limo. I used to brag that the limo is so long that the area codes on the front and rear telephones are different

    Like 4
  8. Tom Crum

    Only automobile I like better than the 1959 Cadillac Fleetwood is the 1958 Cadillac Fleetwood. It had about 100 pounds more chrome hanging on it.

    Like 3
  9. Joe

    What a gorgeous car! I miss the days when you could instantly identify what make and model it was.

    Like 14
    • Emel

      The nondescript cars of today, mirror the group think & group herd mentality being pushed. The individuality of the cars of the past….expressed individualism, which is being stomped into oblivion.

      Like 3
  10. Jim

    I was 16 and attempting to get my driver’s license in my parent’s 1959 coupe de ville. I did well in everything but trying to parallel park that beast. The DMV passed me out of sympathy

    Like 18
  11. Jack M.

    I would coat everywhere that I could reach on the underside with POR 15 before it gets any worse.

    Like 7
  12. Bob_S

    A 59 Cadillac is easy to drive. All 4 corners are clearly defined by the gunsight in front and the fins in back. I find it’s easier to drive than my F150 crew cab, they’re about the same size. So if you can drive a pickup truck without killing somebody, then you can easily drive a 1959 Cadillac.

    Like 9
  13. Bob_S

    Matter a fact I just lookup the length of the f150 and its ~232” and the 59 Cadillac coupe is ~219”.

    Like 3
  14. FordGuy1972 FordGuy1972 Member

    I had a ’60 4-door hardtop Caddy which was very similar to the ’59 models and yeah, it was big. I drove moving vans at the time (1980s), so size wasn’t an issue for me. I could parallel park the Caddy without too much effort, you just have to know how to use your mirrors. I parallel parked the moving van I drove quite a few times, too; especially when I was in NYC. This Cadillac is an absolute beauty and worth every penny.

    Like 6
  15. Dave Brown

    The promise of flying cars never happened. I am from that era. It’s seems like a fantasy now. Everything has gone to hell since then. God bless us all!

    Like 7
    • 370zpp 370zpp Member

      Dave, I feel your pain. No flying cars like Popular Science promised us. No shuttle busses to Mars either.

      But we do have ten varieties of Oreos to choose from on any given day and telephones that are so small you can barely use one as a lethal weapon anymore.


      Like 4
    • PRA4SNW PRA4SNW Member

      There’s still hope. Look it up – George Jetson was just born the other day.

  16. Roseland Pete

    Compare the styling on this car to what car companies have been turning out the last few decades. At what point did the the car companies disband their styling departments or maybe a federal law was passed outlawing nicely- designed cars.

    Like 11
  17. Karl

    A Rick Payton Restoration.

    Like 3
  18. Steve H

    Safety standards, fuel economy standards, emissions standards, and affordability put the kibosh to cars like this. Today’s cars and trucks are amazingly well built and efficient compared to the good old days. Oh well, time marches on.

    Like 1
    • Emel

      Actually fuel mileage hasn’t changed substantially in over 20-25 years. So how is that amazingly efficient ? And you can’t even attempt to work on thse garbage cars of today. All of this done on purpose. And the cost of cars is outrageous as well. You’re paying on these things for 5 & 6 years.
      They were certainly the Good Old Days.

      Like 2
  19. Tom

    Stumbled across a 1962 Eldorado convertible at age 19. It had 26K on the odometer and looked like brand new. Was the green with green top and green leather interior. I was “pimpin” and thought the world was my oyster. Here’s the deal, I only paid 800.00 for it and the seller, (an elderly woman) threw in a joint to boot. AHHH… those were the days!
    p.s. a large cooler for drinks fit behind the back seat like it was meant to be there. What a car!!

    Like 5
  20. Steve Clinton

    Back when a Cadillac was a CADILLAC!

    Like 8
  21. Bruce

    I can relate to Jim’s drivers license story. I was fiddling with a 68 VW super beetle at home awaiting turning 16. The day I turned 16 I couldn’t get it started. I asked my mom if we could go let me take the test and use our 64r Buick LeSabre. The size didn’t cause a problem with the driving test since I had been driving our old 3 speed on the column pickup truck around the farm But at the end he asked me to parallel park in front of the DMV. I asked him ow long did he have to wait while I tried to park it? He said….”Because?” And I told him I had never parallel parked ever. He asked, “Are you going to drive this?” I told him no, I had a 68 beetle at home already inspected. He just got out, said “Find a spot to park this and come in and get your driver’s license.” Oh the good old days were common sense prevailed. To this day I can’t parallel park. Try hard to never try.

    Like 10
    • Dale S

      I can remember my driving test taken in a 1965 Pontiac Catalina sedan, given by an ‘old school’ deputy sheriff. When I had drivers training, my instructor told me after I turned a corner to accelerate immediately to the posted speed limit. He said that it would impress the deputy. It made sense to me. During the test, I was asked to parallel park the beast. I had two tries at it, and failed. He took six points off for that. I lost another two points for failing to use my turn signal when pulling away from a curb. After that I was zoned in. I passed with a 92 on my drivers test, but when I got back in the car, after the test was over, I asked my instructor to drive. He insisted that I drive. I lost it. I don’t remember exactly what I did, but my instructor told me if the deputy had seen that, I wouldn’t have passed. Ah, the sixties!

      Like 2
  22. GTOMAN455

    The car is Spectacular, but you better have a long garage. And a gas card. LMAO. awesome piece of US automobile history

    Like 2
  23. Fran

    It’s in Austin Texas???? Why isn’t it electric?

    Like 3
  24. Michael Berkemeier

    Who was the idiot that installed the Flowmasters?

    Like 1
  25. matthew grant

    we had the identical car. my stepfather was a Chrysler dealer and someone traded one for an imperial and he dumped it on my mother. it was pretty nice.

    Like 3
  26. Anthony Caruso

    I was a sixteen year old from Northern Ontario working in Chicago for a tile company. I had to run errands for the office and got to drive one of several white 59 Caddy coupe de ville cars parked by the office. It was an amazing experience for a young Canadian kid from the sticks. To this day I thrill when I see one in a parade.

    Like 2
  27. Emel

    The Space Race was in the 1960’s not the 1950’s, after JFK’s famous speech….to be the first to the Moon. Astronaut Alan Shepard was the first American launched into space on May 5, 1961, a couple weeks after Soviet cosmonaut Yuri Gregarin’s first human in space. Mercury led to Gemini which led to Apollo. Moon in 1969, Apollo 11.

    • bill tebbutt

      I had to look it up, as I thought it was earlier. Apparently, Aug. 2 1955 was the technical start of the space race, when the USSR responded to the USA’s statement that it would be working to launch a satellite with its own statement to the same effect. So this piece of automotive gold was designed and sold well into the space race.


      Like 2
      • Emel

        I would suggest that most folks in the 1950’s thought little about a space race. What they were saturated with was; a plethora of Hollywood sci fi movies with Rocket Ships and space aliens and Ufos.
        Movies like Forbidden Planet, Destination Moon, The Day the Earth Stood Still, The Thing from Another World, When World’s Collide, Red Planet Mars, Invaders from Mars, It Came from Outer Space, The War of the Worlds, This Island Earth, Earth vs The Flying Saucers, World Without End, From the Earth to the Moon, and dozens of others. This is what caused Detroit to change it’s styling to rocket fins, etc. Not some statement made in 1955…that very few people in America even took note of. Indeed Cheers. Happy Hour !

        Like 1
    • GitterDunn

      NASA considers Russia’s launch of the Sputnik on Oct. 4, 1957 to have been the start of the space age, and the USA-USSR Space Race.

      Like 1
      • Emel

        Well that’s interesting cause NASA wasn’t even established until July, 1958….so it was hardly in the majority of Americans minds.
        What brought it into the national consciousness was JFK’s speech in 1962 and only after that…. did NASA’s budget grow exponentially.
        Prior to that year of 1962, NASA’s budget was a minuscule 1/10th of 1% of the US budget. Hardly representing a Space Race.

      • bill tebbutt

        Emel, I wasn’t around in the 50s, so to determine what happened when, I have to research it. The space race originated in the 1950s.

        “After the successful launches of Sputnik I and II, President Dwight D. Eisenhower rapidly advanced the development of the United States space program. Within months, Congress passed legislation establishing the National Aeronautics and Space Administration (NASA). In this photograph, President Dwight D. Eisenhower presents commissions of office to Dr. T. Keith Glennan (right) as the first administrator for NASA and Dr. Hugh L. Dryden (left) as its first deputy administrator, during a White House ceremony on August 19, 1958.”

        The bold/brave/ambitious/amazing decision to go to the moon was certainly a monumental achievement in the space race, but it did not start it by any means.


        Like 1
  28. RallyAce

    I only need to add 6 feet to the depth of my garage and increase the door height by 2 feet so it can hold this beauty. I guess I won’t be bidding on this one.

    Like 2
    • 67Firebird_Cvt Member

      Around here, Northern KY, it is not unusual to see small old frame garages behind houses that have several feet added to the front for when cars became longer. Our house, built in 1907 had a small frame garage and it was added onto sometime back for this reason.

      Like 2
  29. Kenneth L Putney

    Drove a 59 Caddy 4dr sedan in HS for my band mates, Sundowner’s, with a U-Haul trailer behind to the Catholic Church on Bunker Hiil Boston MA for a gig. Tight streets but made it in and out with out a hitch.

    Like 2
    • Bill McCoskey Bill McCoskey Member

      “Tight streets but made it in and out with out a hitch.”

      But . . . but . . . . but, How did you tow the trailer without a hitch?

      Sorry, the devil made me say it!

      Like 3
  30. Chuck Dickinson

    The only folks who ‘shiver’ at the thought of driving a ‘barge’ this size are those who obviously were born too late. These were normal Cadillacs to me since that’s what was on the streets when I was growing up. Never bothered me driving one, and a 59 Cad will actually fit into my garage with about 2″ to spare!

    Like 3
  31. Motorcityman Member

    A work of art for sure, BUT……I remember how my first car a 73 Ford Galaxie 500 felt like it was going to roll over when u took a curve at ANY speed.
    I can imagine how this feels!!

    Like 1
  32. Motorcityman Member

    “ROSWELL” was in 47, hence the “space race” of the 50s.
    Maybe, maybe not!
    Our technology seemed to advance pretty quickly, maybe we learned a lot from those little green men.

    Like 1
  33. John Muller

    When I was growing up in the suburbs outside of Detroit my grandfather on my father’s side was a truck mechanic and gained a local reputation for being a capable and fair person so he was always wrenching at his own garage. At one point my uncle had bought 2 early 60s Cadillacs, both white and my grandfather had one as well all bought used and cheap in the 70s. Those cars rode well and had power everything and cigarette lighters and metal ashtrays in every door. Sweet memories. Someone had taken a photo of the three of them parked in the street outside my grandparents house. Wish I had that photo now. I thought I would share as I enjoy reading the comments from others.

    Like 4
  34. Angel_Cadillac_Diva Angel_Cadillac_Diva Member

    Same old story, Rex, Europeans want red/red and we want yellow/red.
    Still curious if the wiring was changed, also.

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