Car of the Week: 1956 Cadillac Sixty Special

dodgechargerfan

In a 55 gallon drum, floating down river, and
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Danny Plotkin’s aching back wasn’t funny at the time, but he can laugh about it now. He knows that if it wasn’t for some unpleasant lumbar pain, he never would have wound up with his favorite ride: a 1956 Cadillac Fleetwood Sixty Special that knocks ’em dead wherever he takes it.

Buying an old, jumbo-sized Cadillac was the last thing on Plotkin’s mind when he was hobbling around the grounds at the AACA Hershey fall extravaganza 3-1/2 years ago. All he could think about was getting some relief from his throbbing back.

“I could hardly walk, so I decided to go out and sit by the cars and wait for my friends so we could go home,” recalled Plotkin, a resident of Longmeadow, Pa. “So I went out there to sit on the curb and lament my bad back, and I look across the way and see a kind of faded ’56 Fleetwood for sale. I said to myself, ‘That Fleetwood looks like a good place to sit. I’ll go sit in that. It’s a comfortable car and I’ll pretend I’m interested in buying it.’ So I waddled over and sat behind the wheel and the old guy who owned it came over and tried to sell me the car — he was dangling the keys and telling me all about the car.”

Plotkin wasn’t overly impressed at first, but the longer he sat in the Fleetwood’s plush upholstery and the more he heard the owner gush about how nice the car was, the more interested he became. When his buddies showed up, a predictable outcome followed. “You know how it is when a pack of guys get together and one of them is interested in car!” he laughed.

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If you're into Cadillacs (I'm not), that's a nice one.

Betcha the re-plating cost as much, if not more, than the body & paint...

I painted a '56 very similar to that one only in Black several years ago. You've no idea just how big these cars are until you're walking around them with a loaded paint gun several times. :O
 
Did anyone else think of Madonna when looking at the front bumper?

I'm not a Caddy guy either, but I do like some of the '60s models and think the '59 is kind of cool. My uncle's first Cadillac was a '65 Deville Eldorado convertible he bought new, and he's never driven anything but a Caddy since. He rarely drove that car. He hung onto it for nearly 30 years and didn't even rack up 40,000 miles. That car was in gorgeous shape; it needed nothing.

I'm sure Stretch remembers the '75 Eldorado in a local yard that's factory orange with T-tops (Hurst Hatches, if memory serves). That's gotta be worth something.
 
Did anyone else think of Madonna when looking at the front bumper?

I'm not a Caddy guy either, but I do like some of the '60s models and think the '59 is kind of cool. My uncle's first Cadillac was a '65 Deville Eldorado convertible he bought new, and he's never driven anything but a Caddy since. He rarely drove that car. He hung onto it for nearly 30 years and didn't even rack up 40,000 miles. That car was in gorgeous shape; it needed nothing.

I'm sure Stretch remembers the '75 Eldorado in a local yard that's factory orange with T-tops (Hurst Hatches, if memory serves). That's gotta be worth something.

the t top eldos are rare as sin.....but if youve ever driven one....you wont want to keep it

the eldo's are the only caddys i dont like..but my love for caddys stops dead at 74..drastic changes were on the way and they got UGLY inside and out....the only car i miss thats been sold parted or left for dead over the years is my 71 coupe deville with its pe smog headded 472....that was a seriously under rated BEAST and fun as hell to drive....

my real complaint about the 50s caddys is if you scroll that direct on nose shot so you cant see the grill only the top half of the car..your looking at a 57 chevy
 
my real complaint about the 50s caddys is if you scroll that direct on nose shot so you cant see the grill only the top half of the car..your looking at a 57 chevy
Well the Bel-Airs were meant to be the "Poor mans Cadillac".
 
Cadillacs never used the same chassis or shared body parts of any kind with lesser brands until well after the '50s. It was just GM's styling department at the time. They were all shooting for a certain "look" and there are similarities between all the lineups in every year.

My uncle's Eldorado was prior to the front-wheel-drive years. It was technically a Fleetwood with the Eldorado package. It looked exactly like this car, but the interior was sort of a cream/off-white color:

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Hey! A good friend had his Grandpa's '66 Coupe DeVille in that colour with the light cream coloured interior. I loved that car! It was the classiest Caddy I've ever seen.
Sadly, he let it rot away behind his shop. He had bought some southern sheet metal for it (both quarters were crunched but zero rust on the car) and let that rot as well. :(
 
the FWD era elodos were a WASTE

i know they share no sheetmetal but they suuuuuuuur looked like it at that moment..
 
When my uncle traded in the convertible at the dealership where he'd bought it and always had it serviced, they wrote him a check. If I recall, it was a '94 SLS that he got out of the deal. They already had his wife's '65 DeVille 4-door hardtop, which he'd traded around '87 after she died. Both were prominently displayed side-by-side in the showroom, with a little storyboard about the cars' histories. They were unrestored but detailed, and behind red-velvet ropes.
 
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very nice...few cars can weather and still look so royal than a caddy..lincoln tryed and failed somehwere in the 50s..the porker and imperial lost the ability in the 60s....caddy finnaly failed with the 76 model year..the 75s had allready lost the grill and tail but maintained the body 1 last year
 
Neither one of those '65s were weathered, despite being in Green Bay, WI from day one. They never sat outdoors, ever. I saw them on display shortly before I left for GA, and they were still in spectacular condition. I actually told the dealer principal, "You've got them lined up incorrectly. The four-door's LH door always faced the RH door of the Eldorado in the garage." He said he would correct that, but I don't know that he did.

Of course, by the time both cars were purchased new, two of their children were of driving age already and had cars, and did a lot of the schlepping of the younger three since my aunt didn't really like to drive anyhow. Both cars were low-mileage, unrusted examples of their breed. The four-door was a light metallic blue hardtop with a white gut. I'd love to know where they are now, as that dealership is long defunct.
 
I don't want to own one but I love the styling of the '50s caddys. I have a few friends with 50's era caddys. I've driven a few of these guys caddys and I must say they are cool cars that are fun to drive. One of those caddys is a 57 2 door eldarado with a factory 2 4bbl set up. Very cool ride even though it needs to be restored.
 

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