Mopar Through The Ages: 1977 Chrysler New Yorker vs 2008 Chrysler Crossfire

History is important to automakers; their reputations are built on years of satisfied customers and brand loyalty. But given a long enough timeline, the only thing a newer model has in common with an older model from the same make is the name on the back. Sometimes they’re better, sometimes they’re worse, and sometimes they’re just different. This week, we’re going to look at two cars of the same make, with decades between them.

We finished up on Friday with a couple of squish-mobiles for cheap. Both choices have a loyal following and a good reputation, so I was curious to see which fanbase would turn up in greater numbers. As it turned out, the Buick LeSabre won, based largely on its better condition, from the sounds of it.

I think that’s the way I would go, as well. I’m not crazy about transverse V6s when it comes time to fix something, but I’m generally more familiar with how GM does things, so I’d be more comfortable under its hood. I imagine the comfort behind the wheel is about the same.

Chrysler has reinvented itself more times than Madonna, and has changed hands more times than the Stanley Cup. The marque is one hundred years old as of this year, and currently sells nothing but minivans. But it has had some bangers over the years, like the Airflow and the 300 letter-series cars. Of course, it also sold the Executive Limousine and the TC by Maserati, but nobody’s perfect. Today, we’re going to look at a last-hurrah big sedan from just before the first bailout, and a sleek coupe from the Daimler days.

1977 Chrysler New Yorker – $3,500

Engine/drivetrain: 400 cubic inch OHV V8, three-speed automatic, RWD

Location: Dallas, TX

Odometer reading: 100,000 miles

Operational status: Runs and drives

The New Yorker was the top of the Chrysler range, one step below the lofty Imperial, which was a separate marque for many years. It was big and flashy, powered by a series of eight-cylinder engines – inline until 1951, V8s after that. Like most American luxury cars, it grew in size up until the 1970s, then was drastically downsized to save fuel. This 1977 model is the last of the big ones, and it is big – nearly nineteen and a half feet long. It’s also the last generation to feature a pillarless hardtop; you can open both the front and rear windows for a huge, uninterrupted swath of fresh air.

One of two large V8 engines lurks beneath this New Yorker’s hood: a 400 or 440 cubic inch big-block. Both used an early implementation of Chrysler’s Electronic Lean Burn system, designed to lower emissions and improve fuel economy. It may have done those things, but it also sapped a lot of power and caused a lot of drivability problems. I don’t know which one this car has, so I’ll assume it’s a 400, and then if someone goes and looks at it and it turns out to be a 440, it’ll be a pleasant surprise. It runs and drives, but that’s all the seller tells us.

The deeply button-tufted seats look pretty good, as does the rest of the interior. The dash top is faded, but surprisingly, considering the Texas sun, it isn’t cracked. Chrysler was operating on a shoestring during these days, and build quality was sort of an afterthought, so don’t look too closely at the fit and finish, and you won’t end up disappointed.

Outside, the paint looks all right, but the vinyl top is shot. The worry is that it has trapped water and started rusting the roof. The photos in the ad don’t give much away, but the area around the rear window worries me a bit. If it were me, I’d plan to strip off the rest of the vinyl and get the roof repainted.

2008 Chrysler Crossfire Limited – $3,850

Engine/drivetrain: 3.2-liter OHC V6, five-speed automatic, RWD

Location: Conroe, TX

Odometer reading: 340,000 miles (!)

Operational status: “Fun and fast” is literally all the ad says

The 1998 merger between Daimler-Benz and Chrysler produced some unlikely offspring, not least of which were the hugely successful LX and LD full-size sedans, which mated Mercedes suspension and driveline parts to a big American V8, and stayed in production forever. Not every child of that particular ill-fated marriage did as well; the Crossfire, a Mercedes SLK-based two-seater with controversial styling, managed to combine Chrysler quality with Mercedes service costs. It takes a special sort of person to appreciate it, and an even more special person to run one up to the sky-high mileage of this example.

The frustratingly terse ad for this car just says “Fun and fast.” I’m going to assume it runs and drives well, based on that. The mileage reported in the ad is almost unbelievable at 340,000, but then again, Mercedes drivetrains have a history of racking up the miles. The single-overhead-cam V6 used in this car is generally known to be reliable, as is its 5G-Tronic transmission. The Crossfire itself has sort of a hit-or-miss reputation, with occasional electrical problems. Maybe if you actually talk to the seller, they can tell you more about this particular car’s foibles.

This is the only photo of the interior in the ad, and it’s not much to go on. I guess I have to assume that, at that mileage, the rest of it is pretty threadbare. Someone has kept it up-to-date with a modern stereo, so you can have CarPlay and Bluetooth and all that good stuff, but it’s not the most attractive thing. But then, the Crossfire’s silver plastic interior always looked a little tacky to me anyway.

Some folks love the Crossfire’s styling; others, not so much. I think it looks pretty good as a convertible, but I’m not sold on the coupe version. The roofline reminds me of an old Rambler Marlin, and not in a good way, and the silver A-pillar treatment sticks out like a sore thumb. Condition-wise, it’s not bad; it just has some faded paint on the bumpers and some cheap window tint slowly turning purple. The headlights could use a polishing, too, but that’s true of most cars this age.

Chrysler in general is a hard sell around here, I realize, but you’ll notice I spared you the entire K era this time. Not that pre-bailout or Daimler-era cars are any great shakes, but big old New Yorkers are cool, and you have to respect anything with over 300,000 miles that still runs well. So what’ll it be – the big white whale, or the little speedboat?