Garage Find: 1955 Cadillac Fleetwood Sixty Special

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The ad lists it as both a ’52 and a ‘55, but this Cadillac Fleetwood 60 Special on Craigslist in the Seattle area is a 1955 four-door sedan. It seems fairly solid, if a bit shabby around the edges. Thanks to Curvette for the tip. Seattle cars don’t rust appreciably, though they get wet a lot! This car doesn’t appear to have been restored, just treated gently. The asking price is $20,000.

The Cadillac’s numbers-matching 331-cubic-inch V-8 has 102,000 miles on it, and that’s a lot of road for powerplants of that era. And we know the engine has issues. The owner says, “I haven’t driven or started the car in about two years. There is a tick when running in the number-eight cylinder. Valve heights are equal (straight edge), pushrods are straight, new lifter in that cylinder, no excessive cam or rocker arm wear. Quiets down when I place my hand on the rocker arm for a brief moment. Could it be a plugged oil galley?” The mechanically savvy are invited to weigh in. A Hydramatic transmission puts the power on the ground.

The body does look good in the slightly fuzzy photos, and the owner asserts it “holds a magnet.”  The paint is reportedly “about 60 percent original.” And the interior, with its expensive-to-replicate multi-color fabric, appears intact, though whether it’s original or not is hard to tell. The carpeting is in nice shape.

We don’t get engine or undercarriage shots, so the buyer will have to take it on faith that the car will run and drive when awakened from its two-year slumber, and that it isn’t falling apart from chassis rust. It’s probably going to need brakes, suspension, a gas tank clean-out or replacement, and miscellaneous odds and ends.

The Cadillac Sixty Special goes back to 1938, with this particular version introduced in 1954, a year before this car was built, with a $4,683 price tag. The Sixty Special model was up a notch from the Series 62. Wheelbase was 133 inches. Amenities added in the new model included better power steering and electric window washers. Options included a four-way power bench seats, power Bendix brakes. The engine now put out 230 horsepower, which was increased to 250 for the ’55 model year—this car.

There were modest styling changes to the Sixty Special in 1955, including a new grille and a $4,342 price, which helped sell 18,300 units. A remote trunk release was added as an option.

These are nice cars, if more than a bit thirsty and floaty on the road. Hagerty puts a 1955 Cadillac Fleetwood Sixty Special at $31,800 in good condition. That makes the ask for this one a bit high, considering it needs engine work and has been sitting for two years.

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Comments

  1. Terrry

    John Travolta owned a ’55 Cadillac convertible in yellow with a white top. Very graceful looking too. This car is kind of chunky with the 4 doors and pillars. It’s certainly distinctive, you knew a Cadillac when you saw it.

    Like 6
  2. Rogue1

    Nice, has the Marilyn Monroe front bumper….

    Like 4
    • Bob G

      These were called Dagmars, named after a busty blonde hostess on the late night Jerry Lester show. I fondly remember hatching the show as a teen ager.

      Like 2
  3. Ken Carney

    After Mom and Dad got married,
    he put us in used Cadillacs as these were the highest quality used cars you could buy in the early ’60s. My folks owned many of them over the years and at least 2 of them were ’55 series 62s– a 2-door hardtop and a ragtop model. Of the two, the ragtop was the sharper of the two. Pea green with a black and
    white interior, REAL wire wheels
    with monster white wall tires, and
    a continental kit out back. Boy, what a car! Sundays were great as Dad would drive us to church in that very car when he was on the day shift as a police officer.
    We’d show up at church with the top down and WLS blaring on the
    radio much to the displeasure of
    Some of the congregation. Showing up in a ragtop? Not in keeping with church policy. Rock
    music playing on the radio? Truly
    the devil’s music! That church was was VERY conservative and
    our family driving a used Cadillac
    ruffled a lot of feathers there. Didn’t get any better when we got
    a second car, Mom always showed up driving a Caddy. In the end, the green ragtop made way for a butter yellow ’59 2-door hardtop, and with it, one of the sharpest Cadillacs that ever was.
    Man, was it nice and I wish I could have it back.

    Like 10
    • Robert

      Hey Ken what part of Chicago did you grow up in ?

      Like 2
    • Wayne

      Hey Ken, Only sinners listened to WLS! Oh well we are all sinners. Thankfully there is a way to be saved from that predicament! Those sound like beautiful cars! I was stuck with 1957 Plymouths (a parade of 7 of them) and an Impala 4 door sedan.

      Like 2
  4. Andy Frobig

    This, to me, is the pinnacle of postwar American iron. I also love the 4-doors. But for what’s going to have to go into it, this is probably a little steep.

    Like 5
  5. Angel_Cadillac_Queen_Diva Angel Cadillac Queen DivaMember

    @Rogue1

    Those were referred to as dagmars after an actress who name was Dagmar and had quite an ample chest.

    @Ken

    Its a Cadillac! Never a Caddy. 😄

    Miss Daisy had a nice 1955 Fleetwood Sixty Special in black. Hers had the little a/c scoops behind the rear doors and would never let Hoke turn the a/c on.

    Like 7
  6. Ken Carney

    I’m sorry dear. Just a slip of the
    tongue. There’s something I’ve
    wondered about for years. Did
    Cadillac ever offer those rubber
    cones that fit over the dagmar itself? Dad had a ’55 that had them, and I’ve always wondered if
    they were an option or something
    aftermarket from J. C. Whitney?
    Did you get the ’58 Lincoln stuff I
    sent you? There’s also a video of
    a ’71 Eldorado wagon prototype
    too. Well honey ❤️, gotta get ready for work. 💋

    Like 2
    • Angel_Cadillac_Queen_Diva Angel Cadillac Queen DivaMember

      Yes, Ken, I got them. Sorry I didn’t get back to you on them I’ve been very busy.
      Looking for a new apartment and dont want to make another mistake. Actually looking for a small house to rent. Plus getting ready for surgery and fixing all sorts of problems I never had in Nevada. Another reason why my presence here has been limited.
      I miss you guys. Ya’ll are family.

      Like 4
      • Wayne

        Well Angel, maybe it sould be back to good old Nevada for you! We miss you here in The Silver State!

        Like 2
  7. hairyolds68

    cool caddy for sure even being a 4dr. i would cruise it with a nice fedora hat. i bet 15k buys it.

    Like 5
  8. TC

    What are electric window washers?

    Like 1
    • Wayne

      A pump that all you have to do is push the button for washer fluid to squirt up on your windshield. Rather than having to manually pump the pedal on the floor.

      Like 3
  9. Bluesman

    Old hippies might buy this for $5k, scrub it down real good, and then use it to cruise around for some laughs. That’s all it’s good for now.

    At one time, when it was more presentable, it was something you’d take to an AACA meet and have some status.

    But nobody cares anymore. It’s now a 4 door novelty car. There is no longer a “collector” market for something like this. All the interested buyers are 75 years and older. Unless you buy it really cheap, you’re gonna lose a lot of money going forward.

    It’s entered the “risk averse” phase of it’s collector lifespan. Risk averse buyers will only buy it very cheap, drive it a bit, and then sell it cheap, with a maximum risk of losing about a grand in the process.

    Like 5
    • Henry DavisMember

      Some people aren’t in the hobby for the money.

      Like 3
  10. Phil Maniatty

    The 1957 Cadillacs had rubber-tipped Dagmars. Other than that, I don’t know of any after-market rubber tip accessories.

    Like 3
  11. Ken Carney

    I”d still buy this car and drive it no matter what the investment people say. It is, a car with good
    bones and would make a top notch driver once all the mechanics are sorted. And that’s
    pretty much all she is and what she should be. You shouldn’t be
    afraid to buy and enjoy your classic car once you buy it.

    Like 6
  12. Bunky

    Dad’s ‘53, also with a 331, consistently achieved 21-23 mpg on the highway.
    $20k is all the money, and more for this nice old Caddy.

    Like 2
  13. Wayne

    Well Angel, maybe it sould be back to good old Nevada for you! We miss you here in The Silver State!

    Like 3
  14. Rodney Lustila

    People with memory of this car are getting up there in age.hard to sell at that price.beauty of a car.

    Like 3
  15. Ken Carney

    Robert, I was a down state boy who grew up in Bloomington which is about 3 hours south of Chicago. I’d listen to WLS, WMAQ, WJJD, and WCFL. My town was home to State Farm Insurance and hosted the Corvette show every summer 🏝️.
    It sure was something to hear Pete Drake play the WJJD jingle on his talking steel guitar 🎸. I got to meet him once at a package 📦 show I was playing in
    1976. He was a real down to earth guy who wore regular suits
    instead of those star spangled outfits that other country stars wore in those days. He and John
    Hale invented the talk box in 1959. It was an electronic gadget with a plastic hose on top
    of it. You sang into the hose, and
    the electronics inside made your
    instrument literally talk. Guys like
    Peter Frampton used them to make their guitars talk in the 1970s. Even Stevie Wonder used
    one of them and made his piano
    talk 🦜 too. I didn’t know who Mr
    Drake was until he played that song called Forever. And Wayne, I used to play in his hometown of
    Crete Illinois once or maybe twice
    a year depending on where they
    sent us. And more likely than not,
    it was a package 📦 show. A package show was just what the name implied. They were organized chaos. You might see
    sword 🗡️ swallowers, acrobats,
    fire 🔥 esters, comedians, and
    whatever else a booking agent could cobble together. Sometimes, we’d open for a big name performer, or all those other acts would open for us. Any way you sliced it, these shows would run 4 hours or more
    to.mske sure that people got their
    money’s worth. We weren’t really
    big stars, but the folks we played
    for made us feel like we were. They really enjoyed the entertainment we brought them.
    I still recall the night that Chubby
    Checker stole my sax 🎷 player at a show in Watseka Illinois by
    offering him more than I could pay him. And now that I’ve taken
    up.enough time, I’d like to thank
    Phil for setting me straight on those rubber cones on those Dagmar front bumpers. If I could,
    I’d buy this car, sort the mechanics, and maybe start playing music 🎵 🎶 on the road
    again. I think I got one more tour
    left in me.

    Like 3
    • Wayne

      Hi Ken, would love to hear you play! Robert, those stations like WGN were “clear radio stations” (IIRC was the term for HIGH POWER stations that reached hundreds of miles transmitting) As Ken mentioned I grew up in Crete. South of Chicago on the Illinois/Indiana border. I was in FFA in high-school as was John Mellencamp who is the same age as me. I’m a big Mellencamp fan and have found out that because of FFA. He and I were in the same place at the same time because we are the exact same age. (I have also been lucky to meet him in person.) He was hugely affected by the same radio stations. Where did you grop up?

      Like 0
  16. Ken Carney

    Wow Wayne! That’s alright! In the last
    band I led, we played John Cougar stuff like Hurts So Good and Little Pink
    Houses. If memory serves, he was one
    of the organizers of the first Farm Aid
    concert in Champaign Illinois back in
    ’85. The most heavy metal song we ever played was (Boom boom) Out Go The Lights by Pat Travers. One of the greatest audience participation songs
    of all time. We played it once at the
    Rosemont Horizon in Chicago back in
    ’79(?). Don’t recall now who we opened
    for that night, but the place was packed. Heard there were 50,000 people there that night, and I got the idea to play that song just for the fun of it. When Travers sang that song , he
    sang the phrase “When I got him in my
    sights, boom boom and the crowd would yell “Out go the lights”. Just imagine all those folks shouting that phrase all at once! The roar was defending. That was the last song we sang before before the headlining act showed up. The crowd went bat sh*t
    crazy and called for an encore which we gladly played. Never saw so many
    flash cubes going off at once in my whole life! If you want to hear the song, you can find it on YouTube. Yeah, I caught hell from the company reps, but it sure was worth it?

    Like 0
  17. Ken Carney

    Wow Wayne! That’s alright! Would like to meet you and Angel
    someday too! Before I retired, I led a band that did some John Cougar stuff like Hurts So Good
    and Little Pink Houses. I wanna say that he was one of the organizers of the First Farm aid
    concert in Champaign Illinois in
    ’85, but I might be wrong about that. The most hard rock song I
    ever played was (Boom boom)
    Out Go The Lights by Pat Travers.
    That was a great audience participation song if I ever played
    one. Played it at the Rosemont
    Horizon in ’79 (?). 50,000 people
    all yelling “Out go the lights” all at
    once was very thunderous indeed. They liked it so much they asked for an encore! Yeah, I
    caught hell from the front office for playing a rock song at a country show but it was worth it.

    Like 0
    • Wayne

      Ken, you talk about the crowd having a large impact on the concert. I was at a John Denver concert at the Stadium down town Chicago. (Same place the Blackhawks used to play.) As John Denver did. He encouraged the crowd to sing along. In the middle of one his songs, he stopped playing and listened to the audience. 30,000 people singing well and in harmony it filled to building. It was so moving it made the hair on my arms stand up. It was almost a religious experience. To this day, that experience moves me. Even John Dever said “WOW!”. Back to the Cadillac, Find a couple of more in good shape, paint them the same color and do an “Old Fogies Tour” .Kind of use the cars as part of the shtick. The cars would haul all the luggage and get a semi (old too?) To haul all the gear. !” WATCH FOR THE CADILLAC TOUR TO HIT YOUR TOWN “! OLD ROCK AND ROLL, OLD COUNTRY WESTERN AND BALLADS THAT YOU REMEMBER FOREVER “!! County Fairs are always looking for entertainment. Do the County Fair circuit!

      Like 0
  18. Ken Carney

    Sounds like a good idea Wayne! We get a GMC Cannonball tractor
    and trailer to Carry all the sound
    stuff. Then you, me, and Angel.would get a chance to meet. Wow! What a day that would be!! I can see it all now. You and I dressed nicely and Angel 😇 wearing a really nice gown. Pure heaven! Shows like the ones you describe are really
    high points for a musician like me. When you bring a crowd into
    your act, you aren’t just entertaining them, you’re interacting with them in ways that
    are very rare today. And that’s why guys like me and others like me took our music over the road
    in the first place. In every small
    town we played in, we brought joy
    and entertainment to folks who may not have gotten it any other way. Yeah Wayne, your Old Fogies Tour is a great idea which I am entirely behind. That way, we can show young people today
    how we played music 🎵🎶 and
    put on shows WITHOUT computers or AI. It wouldn’t be perfect, but nothing ever was back then. Yeah, I’d be more than
    happy to do a tour like that. Nothin’ fancy, just maybe a 10 or
    15 City road trip to relive the old days one last time. A car like this one would be a blast to use as a
    tour piece too… And would I still
    be able to do a one nighter with a
    young lady? I’d like to try that too.

    Like 0
    • Wayne

      Know any promoters that would bank roll the thing? Maybe do a hot rod tour along with the music. One of our group used to do the world of wheels shows.
      And I think another promoted concerts. We’ll guys what do you think?

      Like 0
  19. Ken Carney

    And you’re right about the fair circuit, we played that too.

    Like 0
  20. Ken Carney

    Can’t think of any promoters right off the top of my head. The Midwest Tour I played in the ’70s
    folded up after the big record companies started sending big name artists to the small towns we used to visit along the way. Before that, the big acts mainly played in the big cities and left the smaller towns for us. I remember the days that if a performer had a number one song in 3 states, that made him/her a singing star ⭐. But now, those days are pretty much
    gone forever. Now it’s massed
    produced soulless music 🎵🎶
    for the masses with the final control coming from New York, LA, or Nashville. There are a few
    outlaw labels left, but not many.
    That would be the place to go if
    if you wanna start a tour like the
    one you’re talkin about. A gimmick? Yeah, we got that! Most of our guys would be in their 40s or 50s at least. I’ve always wanted to have a young VS old competition just to see who would win. And there are valid points for both sides. Our
    younger friends may have that AI
    flash and dash, but WE have the
    soul and the know how to sing a
    song and make you feel it. The kids don’t. The suits at the record
    companies won’t let them play and sing the way we did and still
    do. And the car shows you spoke of, companies like Midwest Entertainment did indeed send bands to those venues to.play.
    It wasn’t all that uncommon to have a friend tell you that they were going to McCormick Place to play a car show there. Midwest Entertainment covered all the bases back then and that’s
    why I liked working for them. You
    played up to 42 weeks a year with
    2 months off that you could use to be at home with your family for
    Thanksgiving 🦃 and Christmas 🎄. Or, you could take up to 5 vacations a year. And by the time I left Midwest Entertainment to get sober in ’79, I had one of those cushy contracts. And by the time I came back in ’81, all of
    the things I knew were gone. The
    company, the tour– gone. So, my
    guys and I played one nighters til
    I retired in 1990. By then, I had a
    A pretty good day job along with a paper 🗞️ route so I felt it was
    time for me to leave the business. Do I miss it? Sometimes. Would I tour again?
    Maybe if the right deal came along. The Old Fogies Cadillac Tour would be the incentive to make me wanna do it. Me, you, and Angel 😇 having the time of our lives. But it’s tough on married people though. You might wanna talk it over with Mrs
    Wayne before you do it.

    Like 0

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