The Six Coolest Cars You Can Buy From $15,000 - $20,000

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Hey everyone, James Reeves here. Thanks for joining the Automotive Icons podcast—whether you’re watching or listening.

If you’re watching, you’ll notice I’m standing because I’m an idiot and I don’t have anything to sit on. That’s because I’ve been renovating this warehouse we’re standing in since last year, and it has been an absolute nightmare. If you’re listening, you can probably hear the reverb bouncing off the concrete. It’s a CMU building with concrete floors, so I’m sure the audio isn’t exactly studio quality. I apologize—I’ll get it sorted by the next episode.

Speaking of episodes: it’s been a few weeks since we’ve done an Automotive Icons podcast. Between the holidays, a bunch of work stuff, and the fact that we’re in the middle of Mardi Gras, things got chaotic. Plus, I’ve been dealing with this warehouse, which—again—has been a royal pain.

But that aside, I’m really glad to be back, because I’m ready to nerd out about cars.

The Mini-Series: The Six Coolest Cars You Can Buy

We’re doing a mini-series: the six coolest cars you can buy, starting at $20,000 and working down to $5,000 or less. We’re breaking it into four episodes:

Today: $15,000–$20,000

Next: $10,000–$15,000

After that: $5,000–$10,000

Final episode: $5,000 or less (that one is going to be rough)

Now, obviously we need rules. If this were just “the best car you can buy,” we’d all say: buy a Camry, Corolla, Civic, whatever, and call it a day. That’s no fun.

So we’re doing six categories:

Smart

Stupid

Strange

Solid

Speedy

Sleeper

Here’s what those mean.

Smart is the responsible pick—cool, but sensible. Something that won’t constantly break, and if it does, it won’t ruin your life to fix.

Stupid is the opposite: a car that’s a terrible idea, but still cool. You might buy it anyway because you’re stupid. (No judgment. I respect the commitment.)

Strange is the oddball pick.

Speedy is the best bang-for-the-buck fast car in the price bracket.

Solid is a proven classic—something with real staying power.

Sleeper is the underappreciated one: good car, undervalued, and maybe on the upswing from an enthusiast or investor standpoint.

One more rule I imposed: you have to be able to actually find these cars. I went shopping today—February 2026—and found multiple examples of each one on places like eBay Motors, Bring a Trailer, AutoTrader, Craigslist, and Facebook Marketplace.

And I put a mileage cap on it: roughly under 60,000 miles. We’ll bend that rule in future episodes, but for $15K–$20K, once you start opening up higher mileage, you get too many weird exotics and “well technically you can buy a…” arguments. I’m trying to keep this realistic.

Alright. Let’s start.

Smart Pick: Mercedes-Benz E-Class (W212) — E350

The smart pick is the Mercedes-Benz E-Class, specifically the E350 W212 generation, produced roughly from 2010 through 2016.

Back in the mid-2010s, Mercedes ran an internal design competition for the E-Class, and the winning design came from a Filipino designer named Wynnie Camacho. And yes, the name cracks me up, because when I was a kid my dad used to say “macho Camacho” as a joke. So it’s funny to me that this car was designed by Winnie Camacho.

This E-Class moved toward a more upright, serious look compared to the previous generation—the one with the four oval-ish headlamps. And midway through the W212’s run, Mercedes did a massive facelift—reportedly an extremely expensive one—which is when they finally killed off the four-headlight design for good.

Is it a little “mature”? Sure. My stepdad had one in navy blue and he absolutely loved it. And I loved driving it. But here’s the thing: it’s still cool. It’s classy. It’s confident. It’s comfortable. It’s a genuinely good car.

These E350s are known for going huge mileage—150,000, 200,000, even 250,000 miles isn’t unheard of. In Europe, you see them as taxis for a reason.

You can find a clean example in the $15K–$20K range all day long. They look good, they drive well, they’re luxurious without being goofy. The biggest downside is the tech: the infotainment is going to feel dated. But that’s part of the trade-off with anything from this era.

Are repairs more expensive because it’s a Mercedes? Sure. But the point is: you won’t be fixing it constantly. It’s a smart buy—and it’s my smart pick, with a shout-out to my stepdad. RIP, buddy.

Stupid Pick: Maserati Quattroporte (Fifth Gen, ~2009–2013)

Now we go to the stupid pick—and I love this one.

This is a Pininfarina-designed car. If you don’t recognize the name, you’ve definitely seen their work. Legendary Italian design house.

And the car is gorgeous. Unfortunately, it also set a record for massive depreciation. We’re talking a car that was $90,000 to $120,000 new, and after five years you’d be lucky if it was worth $40,000—sometimes less.

You probably already know what I’m talking about: the Maserati Quattroporte.

“Quattroporte” literally means “four-door,” which is the least interesting name imaginable. But the car looks fantastic. The first-generation Quattroporte was especially beautiful, and over the years the styling has ranged from “stunning” to “what were they thinking?” The one we’re talking about here—the fifth gen—falls in the “still pretty” category.

Here’s a story: one of my best clients called me—some of you may not know I’m a lawyer in my day job—and says, “James, we’ve got a problem. My wife totaled her car. We paid over $120,000 for it, and the insurance company is offering under 30 grand.”

And I was like, “Mike… that’s what happens when you buy a Maserati.”

Whether the reliability reputation is fair or not, it exists. Service can be a headache depending on where you live. And a big reason these collapsed in value is that so many people leased them, beat on them, then dumped them back onto the market at the same time—flooding the used inventory.

So yes: you can buy a $100K+ car for $15K–$20K, which is insane.

But here’s the killer: the repair costs don’t care what you paid. A $10,000 repair is a $10,000 repair whether it’s a $200,000 Maserati or a $20,000 Maserati.

That’s why it’s the stupid pick. Beautiful, dramatic, Italian… and probably always in the shop.

Strange Pick: Chevrolet Corvair

The strange pick is a bit of a heartbreaker: the Chevrolet Corvair.

Chevy sold nearly two million of these, but you don’t see many today. They were commercially successful, well-liked, and they helped push the American market toward smaller, more efficient cars.

And then the Corvair got hit by one of the most infamous pieces of automotive PR of all time: Ralph Nader’s book, Unsafe at Any Speed. The Corvair became the face of the controversy over oversteer and handling.

Chevy fixed the issues. And later, a Texas A&M study conducted for what is now the NHTSA concluded that the Corvair wasn’t meaningfully more dangerous than many comparable cars of the era.

But the damage was done. The American market doesn’t forget, and the Corvair eventually died off.

From an engineering standpoint, it was ahead of its time: air-cooled flat engine, rear engine/rear drive layout, independent suspension, tons of innovation. Motor Trend Car of the Year in 1960. Time magazine called it a forerunner of a new age in Detroit. It was genuinely important.

In our budget constraints, this is the dicey one—you’ll be pushing the top end of the $15K–$20K range for a truly clean example with low miles. But it’s doable if you hunt.

Would I buy one? Probably not. But it’s fascinating, historically important, and undeniably strange—so it’s the strange pick.

Speedy Pick: 1992–1996 Chevrolet Corvette C4 (LT1)

Alright, speedy.

I can’t believe I’m saying this because I kind of hate this car—and I hate the stereotype that comes with it. You know the guy: jean shorts, New Balances, calf-high crew socks, Corvette hat, Corvette jacket, Corvette memorabilia in the house, and the original build sheet framed on the wall.

But for $15K–$20K, I can’t find anything better if your goal is just: fast.

The pick is the 1992–1996 Corvette C4 with the LT1.

Even the “standard” LT1 car is quick. Low-4-second 0–60 is achievable depending on the conditions and setup, and quarter-mile times in the 13s are common. And it got there with lightweight composite body pieces, a low center of gravity, independent suspension, big brakes, and a chassis designed for sustained high-speed running.

The C4 also set multiple speed and endurance records, including a particularly absurd one: a 24-hour endurance run with an average speed well into triple digits. It’s insane.

Is it ugly? In my opinion, yes. The interior looks like it was designed by someone who got paid in cigarettes. But it’s fast, cheap, and proven.

That’s why it’s the speedy pick.

Solid Pick: First-Generation Ford Mustang (1965–1966)

Now for the solid pick: a real classic.

I could probably pick the same car in every budget bracket and save myself time, but I’m trying not to cheat.

For $15K–$20K, the solid pick is a first-generation Ford Mustang, ideally a 1965–1966 coupe or convertible.

This was my first car: a 1966 inline-six “plain Jane.” No A/C, in Florida. It was hot as hell, rusted out, and I did the Bondo work myself. I installed a Pioneer CD changer like I was living in the future. And even though it was imperfect, it was still cool—because it was a Mustang.

For $15K–$20K you can get a genuinely solid example—just don’t expect a fastback or rare engine codes in that range. A clean coupe is the sweet spot.

Parts support is absurd. Everything is available. The engines are simple, reliable, and easy to work on.

The big thing to watch is rust. Check the undercarriage, wheel wells, and especially floor pans and cowl areas. Leaves collect in the cowl, trap moisture, and can rot the structure and dump water into the cabin.

Engine choice? If you can find a clean inline-six car, there’s nothing wrong with that—unless your ego needs the V8 badge. The 289 is the classic move, but either way, it’s a timeless car that fits anywhere. You can pull up to the nicest restaurant in a clean ’66 Mustang and nobody’s turning their nose up at you.

That’s solid.

Sleeper Pick: Nissan 300ZX (Z32)

And now the sleeper—the one I think is still undervalued, but not for long.

When you talk Japanese sports cars, the Skyline GT-R is long gone value-wise. Supras have climbed. NSXs are way up. RX-7s have climbed. So what’s left that’s still achievable?

The sleeper pick is the second-generation Nissan 300ZX (Z32)—the Fairlady Z in Japan.

You can still find good examples in the $15K–$20K range, though you’re starting to see them creep upward.

This car was acclaimed when new:

Car and Driver 10Best multiple years in a row

Motor Trend Import Car of the Year (early 1990s)

One of the earlier cars heavily developed using CAD

The twin-turbo VG30DETT is the headline: a 3.0L V6 with parallel turbochargers, making over 300 horsepower, with 0–60 around five seconds in period trim. Still legitimately quick.

There are also fun cultural footnotes—famous ads, controversy over street-racing perceptions, and even parts crossovers in the exotic world. The point is: it’s a great car, it’s gorgeous, it has pedigree, and the window is closing.

That’s why it’s the sleeper.

That’s all I’ve got for you on Automotive Icons today. I hope you enjoyed it—I did. I love digging up these fun facts, and this series has been a blast to research.

Stay tuned, because the next episode is going to be a lot harder: the six coolest cars you can buy for $10,000 to $15,000.

Make sure you like, subscribe, and all that good stuff. Thanks for watching. Take care.

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