Klassic Kenny: The Mysterious 1950 Oldsmobile 88 Holiday coupe

If you ask retired Old Cars Weekly Research Editor Kenny Buttolph what kind of man he’d call himself — and I have — he’d say he’s a Buick man. That surprised me — I had him pegged as an Olds man through and through.

If you know the vast quantity of cars Kenny has owned (more than 1,200 by last count) and the variety he still owns, you can begin to understand there is room for confusion. Of the cars he still owns — Kaisers, Chevrolets, Fords, Metropolitans, Chryslers and, of course, Buicks and Oldsmobiles — his favorite for the last 10 years or so has been a 1955 Oldsmobile Ninety-Eight Holiday coupe we featured a few years ago. That story also included some tales of Kenny's years working at a Wisconsin Oldsmobile dealership back in the day.

But this is the story of another Olds altogether. An Olds of mysterious origins.

Somewhere between buying his current '55 Olds Ninety-Eight and working at the Olds dealership when ’55s like his would have been new cars, Kenny bought an unusual 1950 Oldsmobile 88. He knows he bought that '50 88 before 1972, because he was able to get the license plate combination “A5088” (get it?) for the Olds before collector plates and personalized plates were possible. And he remembers that Wisconsin began issuing collector plates in 1972, because he selected collector plate number 72 as his personal number to remember the year in which the bill passed.

Besides the fitting “A5088” license plate, Kenny's unrestored and unmolested 1950 Olds was special. Not only because it was a first-year 88 two-door hardtop, but because his was an especially early car. As a result, the car appeared more like a convertible with a hardtop attached more than a car built to be a hardtop. To this day, Kenny cannot explain the hardtop’s several unusual features, some right off the convertible. That's what makes this Olds somewhat mysterious.

“With the hardtop visors, you could block the sun from the side window, but not mine,” Kenny said. “They would only swing up and down like on a convertible.”

Early 1950 88 Holiday coupes have a two-piece windshield, as on a convertible, while later cars had a one-piece windshield. Kenny’s ’50 Olds Holiday coupe had the early two-piece windshield as well as an unusual finish to the windshield header.

Kenny said header panel above the windshield on most of those first-year 1950 Oldsmobile 88 two-door hardtops was fabric-covered, but the header on his highly original car was painted, and there were grinder marks visible under the original dark green paint. The exterior was the same dark green color and it, too, was the original paint sprayed by the Fisher body plant, yet something didn't add up.

“The green was not an Oldsmobile color,” Kenny added. “I got some Olds paint and nothing would match until I found a Pontiac color, and it was a match.”

Incidentally, the interior consisted of dark green leather with tan bedford cloth inserts. Kenny recalled the instrument panel was painted a two-tone silver-gray and a green that matched the exterior.

Kenny said in the early 1970s he took the ’50 Olds to what he thought was the club’s first Oldsmobile meet and members were crawling all over the car's unusual features. Yet none f them could determine with absolution why Kenny’s 1950 Oldsmobile was different. (My guess is that it was some kind of pre-production car.) Kenny didn’t really care. He simply liked it because “It was just a nice car.”

We’ll probably never know the backstory of the car. The car is long gone from Kenny's collection, having been sold to a man in Racine, Wis., who was a longtime friend of retired Old Cars Weekly staffer James T. Lenzke. That subsequent owner would call Kenny about once a year to tell him he'd took the car around the block before putting it back in storage. Then, one year, the new owner contacted Kenny by mail instead of phone and gave him a dramatically different type of update.

“I got pictures and they showed that they painted it black and put in a red interior and made it like everybody else’s,” Kenny said. “I never heard from him since.”

Without record of the car's trim tag or serial number, and the tie to the subsequent owner lost with Lenzke's recent death, it would be hard to track the car now.

Somewhere, there’s an unusual 1950 Oldsmobile 88 Holiday coupe driving around and its owner may not know how unusual it really is, or was. Perhaps it’s even your car. If you think it may be, drop us a line at oldcars@krause.com.