Ah, classic American cars. All tail fins, V8s, and chrome, right? Wrong. While the golden age of the ’50s and ’60s still plays an outsized role in the American classic car market, new generations and new open-mindedness are propelling cars that previously weren’t seen as classics to new heights. Oh yes, it’s time to go post-’73. Way, way post-1973.

Welcome back to Gavel Gazing, where we take a look at cars that have recently sold on internet car auction sites and share what’s piqued our interest. First, a disclosure for anyone speculating: None of these cars are the next big thing, because anyone certain about the next big thing is either pumping hype or just guessing. These cars are the new big things, unexpected movers in an unexpected market.

I blame David Tracy. Alright, not entirely, but spreading the gospel that the Jeep XJ Cherokee is God’s gift to mankind may have played a role in the unyielding rise in values over the past few years. Case in point? This 1998 model with 109,000 miles on the clock just hammered for new Hyundai Tucson money: $27,500. My jaw is on the floor.

This Cherokee isn’t perfect. It has its fair share of paint imperfections, It’s been fitted with aftermarket headlights and clear side markers, it spent most of its life in Maryland, and yet it still went for big money. Don’t get me wrong, its still a rather nice example, but collector appreciation of the Cherokee has been positively meteoric.

Back at the start of 2017, the most expensive Jeep Cherokee sold on Bring A Trailer went for $12,500. Now? This thing hammered for $27,750, and it didn’t even come close to setting a record. Bring A Trailer is known for flukes, but this particular XJ Cherokee isn’t one of them. What’s more, values aren’t exactly contracting, in spite of what we’ve seen in much of the traditional enthusiast car market. The floor for these things is still trending upward, so who knows where it could land?

And now for something completely different: Cadillac’s penultimate attempt at a truly old-school flagship. Resplendent in faux wood and sheer acreage of sheetmetal, this barge wasn’t about speed, handling or precision, but instead a way to cruise across America in the highest comfort possible. Sure, the 5.7-liter V8 may only make as much horsepower as a new Mazda 3, but the air-con in these things is ice-cold, and the seats just let you sink right down. It’s a classic mentality, just engineered in the ’80s.

Like the Jeep Cherokee, these Cadillacs used to be cheap, but suffered from attrition at the hands of teenagers imagining the possibilities of a bench front seat, proper skint people who just needed something durable, and the executions of wills. I, for one, am glad to have grown up on the tail end of land yacht affordability, as experiencing a full-size body-on-frame American sedan is something everyone deserves.

While certainly in decent shape, this isn’t an exceptional Brougham, with dings, paint imperfections, and all the hallmarks of a car that’s seen regular life. There’s a little bit of rust, a little bit of wear, and plenty of indication that this car was loved, but not exactly preserved in amber. Still, it fetched $10,500 on Bring A Trailer, a solid result level with what we saw in both 2021 and 2022. Five figures might just be the new normal for a nice Cadillac Brougham, especially with another generation of enthusiasts seeing these as classic cars.

Here’s a sentence I never expected to say: Overall Chrysler K-Car values on Bring A Trailer are still on the way up. More than just a punchline in a Barenaked Ladies song, the K-Car redeemed Chrysler, despite however crappy the actual cars were. Arguably, the K-Car also changed North American cars forever, with widespread platform sharing, heavy adoption of front-wheel-drive, and spawning a little thing called the minivan.

Sure, the Dodge 600 ES Turbo Convertible isn’t the most desirable K-Car, but it’s still a turbocharged four-seat convertible, which means it’s basically a Bentley Continental GTC. Indeed, just look at all the luxury you get in this thing. I’m talking electronic digital instruments, loads of metallic interior accents, white seat covers, and the convenience of an automatic transmission. That doesn’t sound like much, mostly because it isn’t, but with a top that goes down and classic boxy looks, there’s an off-brand John Hughes appeal to this thing.

While this Dodge 600 ES Turbo Convertible certainly isn’t the most expensive K-Car to hammer on Bring A Trailer, it definitely isn’t the cheapest despite certainly not being the nicest that’s hammered on Bring A Trailer. Considering it was only seven years ago that a LeBaron GTS set a then-high bar on Bring A Trailer at $1,950, this has certainly been an ascent to watch.

1996 Ford Explorer: $6,600

Hey, here’s something else with a controversial past that’s no longer a scrap value car: The second-generation Ford Explorer. Fewer than 25 years ago, the Explorer was embroiled in a bitter legal battle between Ford and Firestone, with lives lost and liability on the line. Now, though? These things are nostalgic, a little trip to a time of post-Cold War optimism.

This Explorer has a lot going against it. It’s being sold as a total mileage unknown vehicle due to an odometer discrepancy, it’s not an especially special spec, and it was torn apart by technical school students in Arizona for years on end. Sure, it might technically be a low-mileage vehicle, but in this case, it’s not the mileage, but the stories it can tell from its life.

Still, this thing sold for $6,600, definitely not the cheapest Explorer to ever hammer on Bring A Trailer, but at the bottom of the current market. Just a few months ago, a pristine two-door Sport model hammered for $19,250, and Explorer values have been on a steady rise on Bring A Trailer.

Objective: Survive

So what have we learned here, other than that nostalgia is cyclic? Well, condition and attrition both affect car prices. There are very few blue chip cars in the grand scheme of things, so the bulk of the classic car market is all about timing. None of us are Michael Burry, so forget about any short-term gains, or even being able to drive a car for free by having appreciation cover maintenance and insurance costs. However, if you buy anything near the bottom of its depreciation curve, keep it nice, and keep it long enough for it to become a classic, you could see a return. It still likely won’t be enough to cover running costs, let alone inflation, but when you’ve fallen out of love or exhausted what you can do, it helps when moving onto the next thing.

(Photo credits: Bring A Trailer)

Support our mission of championing car culture by becoming an Official Autopian Member.

Got a hot tip? Send it to us here. Or check out the stories on our homepage.