Off-Season Drop-Tops: 1990 Chrysler LeBaron vs 1994 Olds Cutlass Supreme

Good morning, and welcome back to Shitbox Showdown! It’s the tail-end of November, with winter coming soon for most of the USA. What better time to check out convertibles? Today we’ve got two early-90s droptops tuned for comfort rather than speed, and both are in remarkably good shape.

Before I show you those, we should check the results from yesterday. Everyone’s favorite erstwhile Swedish automaker pulls out another win, with that red 900 Turbo absolutely crushing the Discovery. A lot of commenters seemed to think the Saab would be “less work,” but I’ve owned a Saab, and I’m not sure that’s true. I think I’ll take the Discovery, myself.

Besides, every summer at the Portland All-British Field Meet, the Land Rover contingent looks like they’re having the most fun. Land Rover club members give rides around the motocross track in the PIR infield in old crusty Land Rovers, and it’s a blast. This year, we took a ride in a beat-up Range Rover driven by a woman whose name I think was Sarah, and we loved it. I “get” Land Rovers now, and an old stickshift Disco would be a great way to join the fun. Yeah, it might turn out to be a Disco Apocalypse, but that’s the risk you take.

Anyway, let’s check out some convertibles. After Lee Iacocca’s revival in the early ’80s, convertibles enjoyed quite a renaissance in America. Almost every carmaker offered one for a while, and usually more than one. They’re relegated to sporty coupes like the Mustang now, but comfy near-luxury convertibles were A Thing for a decade or more. Let’s take a look at two of them from the early 1990s.

1990 Chrysler LeBaron Convertible – $3,750

Engine/drivetrain: 3.0 liter overhead cam V6, four-speed automatic, FWD

Location: Phoenix, AZ

Odometer reading: 81,000 miles

Runs/drives? Yep!

I’m not sure what corner got turned in the Chrysler design department in the mid-1980s, but thank goodness for it. The K-cars, for all their virtues (and they had many, don’t roll your eyes like that), were not what you’d call stylish cars. Fortunately, the stodgy upright look was gone from nearly all of them except the traditional full-size sedans by 1990, and a sleeker, more modern look had taken over. And the Chrysler LeBaron, of all things, was one of the best examples.

Under the sleek hood was a welcome horsepower and torque infusion from Chrysler’s Japanese partner Mitsubishi, in the form of a three-liter V6, shared with many other Chrysler and Mitsubishi vehicles. There’s nothing remarkable about it, good or bad; it has a tendency to burn oil at higher mileages, but otherwise keeps pumping out middling amounts of power to the front wheels through, in this case, Chrysler’s then-new and unproven Ultradrive four-speed automatic. A lot of these early Ultradrives had problems, mainly due to improper maintenance, but if this one has been kept up as well as the rest of the car appears to have been, I’m sure it’s in fine shape.

This LeBaron has a scant 81,500 miles on its futuristic digital odometer, and it looks like it. Normally seat covers are a bit of a red flag, but in this case, I have a feeling they’ve been on there since 1993 and the seats are immaculate underneath. I could be wrong, but this doesn’t look like a car that has led a hard life.

I expect to hear the usual barrage of LeBaron references in the comments: Jon Voight, Kitty/Karen, etc. But make sure you don’t miss the obvious one. Otherwise, I’ll have to tell you that we used to be friends.

1994 Oldsmobile Cutlass Supreme Convertible – $4,000

Engine/drivetrain: 3.1 liter overhead valve V6, four-speed automatic, FWD

Location: Reno, NV

Odometer reading: 167,000 miles

Runs/drives? Sure does!

K-car just isn’t your style, and nothing I say can convince you? Fair enough. How about General Motors’s slightly larger chassis-that-went-under-everything, the W-body? Here we have a model unique to the Oldsmobile brand, a drop-top Cutlass Supreme. It’s not quite the full open-air experience that the LeBaron is, due to that basket-handle roll bar, but I can’t fault it too much, because it retains the W-body coupe’s coolest feature: those door handles in the B-pillars. I don’t know why, but I always thought those were neat.

Powering this Cutlass is GM’s ubiquitous 60-degree pushrod V6, the engine nobody loved, but everybody bought. Like the Chrysler/Mitsubishi V6 in the LeBaron, it’s just sorta there, occasionally developing piston slap, or springing a coolant leak, but otherwise chugging along. GM’s 4T60E Turbo-Hydramatic handles the gear-changing duties.

THis car has more than twice the miles on it that the Chrysler does, but you wouldn’t know it to look at it. The paint is shiny, the interior is rip- and stain-free, and apart from a missing Oldsmobile emblem on the nose, I can’t really see anything wrong with it. It runs and drives great, according to the seller, and has a stack of service records and receipts from recent repairs.

I always liked the W-body Cutlass, and I think it makes a handsome convertible. Or is it technically a cabriolet, because of the basket-handle? I can never keep that all straight. Whatever. It’s a good-looking car with a top that goes down.

I know there are those of you that hate convertibles, and having owned one myself for several years, I understand why. It’s a pain in the ass at times. You can basically never lock it, for fear of someone just slicing open the top to break in. It’s always too hot or too cold to drive around with the top down, except for those few perfect days of the year. And when you drive with the top up, you’ve got blind spots the size of the Queen Mary. But the romance of them is undeniable, and when you do get those perfect top-down days (or nights; driving a convertible at night is an absolute treat), you tend to forget all that other stuff. And these two happen to be pretty good cars, independent of their convertible-ness. So which one will it be?

(Image credits: Craigslist sellers)