Flagship Drop-tops: 1990 Mercedes-Benz 500SL vs 1970 Oldsmobile 98

Shitbox Showdown Flagship Ragtops
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Hello everyone and welcome to another edition of Shitbox Showdown. For a brief period of time, I’ll be taking over duties from Mark in the wonderful task of separating the “or best offer” wheat from the “no lowballers, I know what I have” chaff. You’ll likely see some minor alterations, but please be assured that the hooptie parade will continue.

For starters, cars in good condition will likely be a little more rare. Bad examples of great cars are just too fun. Secondly, pricing will somewhat vary as shitboxes exist across the entire automotive pricing spectrum. That 1989 Volvo 740 sitting on a lawn with a dollar store for sale sign in the window? Possibly a shitbox. That high-mileage 2008 Toyota 4Runner from a rust belt state? Probably a shitbox. That rebuilt-title former-rental Ferrari 360 sitting at your local buy-here-pay-here dealer? Most definitely a shitbox.

While I’ll still try to stick to a reasonable budget cap, today we’re exploiting the joke that Canadian currency is basically worthless. Even though the weather’s cooling down, the deals are heating up as everyone’s looking to offload cars before paying for winter storage. But first, let’s take a look at the results from yesterday’s showdown.

Charade Poll

Huh, looks like only me and 99 other people wanted to play charades. This isn’t just a victory for the LTD, it’s a slaughter. Given the car’s condition, it’s easy to understand why. That Fox-body Ford is ridiculously clean for $2,500, plus parts availability is likely superior compared to the Daihatsu. Anyway, let’s get into the main event, where we’ll be looking at two flagship cabriolets from very different eras. Drop temperatures, drop tops, drop dead, etc.

1990 Mercedes-Benz 500SL – $5,000 Canadian

500sl 1

Engine/drivetrain: Five-liter 32-valve V8, four-speed automatic gearbox, rear-wheel-drive

Location: Brampton, Ontario

Odometer Reading: 260,000 kilometers

Runs/drives? You bet.

When you think of flagship cars, a bevy of Mercedes-Benz models likely come to mind. The S-Class is the definitive plutocrat express, Bobby Ewing had an R107 SL, and every lifestyle of the rich and famous tends to include a Geländewagen of some sort. Still, aside from a handful of much more expensive models, the gorgeous R129 SL might just be the pick of the bunch.

500sl 4

As this is a relatively early R129 500SL, it gets some tasty treats that later cars were deprived of, starting with the 32-valve M119 V8. This dual overhead cam wonder pumped out 322 horsepower, 20 more than the later M113 V8. Despite the four-speed automatic gearbox, this thing’s still quick by modern standards, dashing from zero-to-sixty in roughly six seconds. The other neat highlight is a motorized interior rear-view mirror, controlled in the same manner as the exterior mirrors. It’s completely excessive yet wholly indicative of an era when Mercedes-Benz built cars to a standard and sold them for whatever that standard cost.

500sl 2

This particular 500SL does appear impressively rust-free, although it’s certainly not without its warts. The front bumper and the plastics ahead of the left door seem to be flaking like a scab, an easy body shop fix but an unsightly issue as it stands. In addition, the complex hydraulic roof reportedly hasn’t been tested, which could prove expensive should it be non-operational, and the seller notes that the car may need a starter soon. Oh, and the gauge cluster appears to be on the rear package tray.

500sl 3

With a little bit of cosmetic work, this Sacco-era cruiser should be a marvelous three-season daily driver. Its interior still looks to be in stellar shape, while a set of somewhat undersized AMG wheels can easily be flogged to make a set of factory gullideckel alloys virtually free. Sure, some big German maintenance bills are likely on the way, but the periods between servicing sound like an absolute dream.

1970 Oldsmobile 98 – $4,800 Canadian

Oldsmobile 98 1

Engine/drivetrain: 455 cubic-inch V8, Turbo 400 automatic gearbox, rear-wheel-drive.

Location: Toronto, Ontario

Odometer reading: 98,927 miles

Runs/drives? Yes

Speaking of flagship drop-tops of bygone eras, how about your father’s Oldsmobile? Okay, your dad would’ve needed to make serious bank to drive a headless 98 back in the 1970s, but this large in-charge barge theoretically fits right in valet parked out front of a fancy restaurant. Forget the eight-ounce sirloin, you’re going for the porterhouse steak tonight.

Oldsmobile 98 2

Like the 500SL, you won’t have to explain what the 98 is, albeit for a very different reason. While the three-pointed star holds luxury appeal, John Q. Public will see a cabriolet with a hood large enough to park a Ram TRX on and assume that you have money to burn and a classic sense of style. Plus, because this is an old car, nobody will care about its fuel economy because it’s retro cool without falling into the fat Elvis Cadillac trap.

Oldsmobile 98 3

However, this big unit will need some work before it’s truly ready for the road. The seller advises that the brakes need bleeding, that a right ball joint needs replacing, and that the gas tank isn’t exactly installed because the car “needs some truck work before the tank can go back in.” Judging by the slightly crunchy door skins, it’s easy to imagine why. Oh, and the convertible top is very much split. Minor details, right?

Oldsmobile 98 4

Still, just look at it. More than 18 feet of primrose yellow land yacht with all the power amenities you’d expect from a classic flagship. So what if a 455 cubic-inch V8 isn’t the cheapest thing to run in an era of expensive gas? This thing is made to eat up the miles in style. Pop an eight-track into the player, set the cruise control, and lord over regular traffic in RAV4s and Civics. The dashboard packs more wood and chrome than Don Draper’s office, the seats look as comfy as anything from IKEA, and the multitude of lap belts suggest that this thing’s at least as practical as a well-equipped Ford Explorer.

So there we are, two posh soft-tops ripe for the picking. Choose wisely between expensive and time-consuming German car maintenance and expensive and time-consuming rust repair.

(Image credits: Kijiji sellers)

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51 thoughts on “Flagship Drop-tops: 1990 Mercedes-Benz 500SL vs 1970 Oldsmobile 98

  1. Be still my booming Boomer heart.

    I saw that gold-rainbow Olds and an invisible, blurry wave tossed me back to an era before the disco-bomb dropped: where Three Dog Night, CCR, and Grateful Dead were layin’ it down, Steppenwolf helped to get our motors runnin’ and we were all damn sure that we were born to be wild…or at least a true nature’s child.

    So, gold for the harvest. Let the hay fly!

  2. I saw that front bumper on the MB and immediately thought “that must be a Brampton car”. Sure enough…

    This is really a choice of do you want to be trying to get the smell of vape and cheap cologne out of the MB or the smell of cigarettes and cheap cologne out of the Olds.

  3. Spicy take: this generation of SL is one of the best looking modern Mercedes. It’s such a simple, elegant design that’s aged like wine. They looked good then and they still look god now…and this one gets bonus points for being in the right color. The greens that Mercedes had on offer in this era were delightful.

    So naturally I’m going SL, although in my humble opinion the ultimate example of this platform would be an SL600 in the same green with a white leather interior. I’m sure it would be a nightmare to keep running but it’s just so perfect. I saw an example get listed recently that was in great shape but I think they wanted close to 20 grand for it…which I don’t really think is worth it. But regardless…90s SLs are a real favorite of mine.

  4. That Olds wouldn’t look out of place at Sunnyvale trailer park. Hey, since we are looking at some Canadian stuff, maybe a Trailer Park Boys duel is in order? Find an old New Yorker, OJ Bronco, etc. and pit them against each other?

  5. My grandmother owned a 70 or 72 Olds Delta 88 sedan. More steel than two Sherman tanks (or 4 Bradley IFVs).

    I gotta go with the Olds and that 455. Nail that dino juice pedal, spin that one tire, watch that fuel gauge fall and feel the battleship start to move.

  6. Rust is forever. Plus, that R129 is in my favorite color. The Merc wins, high repair bill be damned.
    Great first day, Thomas! Thank you for your service.

  7. Olds any day over the Merc. We had a 1970 Buick Electra 225 convertible, with the Buick 455. Lost the storage space, and it was starting to rust due to the unavailability of storage. But that was one of the best cars EVER. The Olds is fixable, parts are available and cheap, the Olds WILL work, and you’ll have waaaaaaay more fun with the Olds.

  8. Boy oh boy. I was poised to jump in here and scream 98 no questions asked all day every day, but that old girl is rough. Those door panels are shot, and the mention of the trunk needing “work” leaves me to wonder what the floor boards and rocker panels look like. The top is split so it’ll leak, which might explain at least why some of the interior looks haggard, not to mention what kind of shape the top’s motor and mechanism are in. Then there’s the issue of having damn near 100k on the clock for an old 455 and what I assume is probably a Turbo 400. While those aren’t terribly complicated to rebuild, they WILL need rebuilt. And trust me when I tell you that it can be a fucking NIGHTMARE trying to find some of the more specific parts of an Olds that isn’t a Cutlass.

    All that said, I’m still going with the 98. MB just isn’t my style

  9. Damn, you’ve come out swinging Tom. I like it!

    Gotta go with the Merc because it doesn’t look like the body would collapse if you leaned against it. That Olds will leave a trail of rust flakes wherever it goes. That would be perfect for Hansel and Gretel, but for the rest of us not so much.

  10. The relative simplicity of the Olds makes it the clear choice.
    A caveman could do most repairs on that beast. The Benz will need a technician to service it.

    1. The problem is that Olds looks like it’s been maintained by Cavemen for decades already. Stick the dash back together and there is always some fool who will buy an old Mercedes. There admittedly ARE some fools who will buy a very neglected 52 year-old Oldsmobile from you after you’ve sunk thousands into fixing the top and the ratty interior, but I think that they’re fewer and farther apart than they were, say, 20 years ago.

  11. Uff-dah. What a choice.
    5K Canadian is about $3700. Unfortunately for both of these beasts I know I can find better versions down here stateside for about the same cost.
    The topless boat is a little harder to find for that cost, regardless of the tinworm munching the sides, so I”ll go with that one.

  12. Those 98’s in LS trim were a dime a dozen in the latter 70’s. They were fantastic cruisers once you did a timing chain job on them.
    A convertible would be a Parade Float, but that one needs way too much.
    A quick search pulled up an immaculate ’67 for $11,900 and you’d have that in this one in no time.

  13. I picked the Olds this time around. The Merc is nice, but have fun with the parts. The Olds can be slammed and stuffed with a 572. And this Olds will look great in Beauberry!!!!!!!!!!!!

  14. Don’t those SLs have some kind of biodegradable wiring that just leads to sadness?

    The Olds doesn’t look like it would take much to be a pretty cool cruiser.

    1. For the R129, ’93-94 are the ones with the biodegradable harness.

      Even if that isn’t an issue, I’ll still take the land yacht Olds over the money pit SL. At least you can fix most of the Olds yourself with parts from O’Reilly’s.

  15. yikes, the 500SL top is definitely going to spew Hydraulic fluid, they all do, but at least it won’t leak as much with that hard surface top on it. I suppose, jut never go roofless. Now if the eco friendly wiring continues to function without shorting at least you could recreate road house and ghost ride it into a monster truck or something. The old is a bit more rough, but if I had to choose, I suppose old school it is.

    1. Yeah, that wire harness would be my biggest concern, followed closely by the top mechanism. The Olds is a boat to be sure, but at least it would be cheap to keep running.

  16. Cheap R129’s are not hard to find so that one would not be worth the extra expense of the trip to Canada and hassle of importing. The Olds wears it’s shabbiness better so I’m going with that.

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