Top Down, Spirits Down: 10 Convertibles That Left Drivers Full of Regret

Convertibles are all about freedom the wind in your hair, sun on your face, and the thrill of the open road. But not every drop-top delivers the dream. Some convertibles come with flimsy build quality, high maintenance costs, or disappointing performance that turns joyrides into headaches. Here are 10 convertibles that made drivers wish they’d kept the top up both literally and financially.

Chrysler PT Cruiser Convertible

Okay, so… the PT Cruiser. I mean, what even was that? It was like they tried to make a retro hot rod but it came out looking like a, I don’t know, a bloated hearse? And then they made a convertible version? Honestly, it was just… sad. The roof mechanism was clunky, it drove like a wet sponge, and it had all the power of a tired lawnmower. You’re paying, what, like $25,000 back in the day for the privilege of looking like you’re driving your grandpa’s weirdly styled, underpowered toy. It was a fashion statement, but the statement was “I have given up.”

Chevrolet SSR

This one is a real head-scratcher. It was a pickup truck? But also a convertible? And it had a retractable hardtop, which was cool tech for the time, I’ll give it that. But the whole thing was just so… confused. It was heavy, the handling was a mess, and the design was so over-the-top. It tried to be a hot rod and a practical vehicle and just failed at both. And for a price tag that could easily push $45,000? Uhm, no. You could’ve bought a proper Corvette and a sensible truck and had money left over for, like, a lifetime of car washes.

Nissan Murano CrossCabriolet

Oh man, this one. Who asked for this? Seriously, who at Nissan said, “You know what our competent, family-friendly crossover needs? To have its roof chopped off!” It was an SUV… that was a convertible. It looked… honestly, it looked like a pregnant roller skate. It was bizarrely proportioned, expensive—we’re talking over $40,000 new—and just completely pointless. It was the answer to a question nobody ever asked. You’d see one and just feel a little bit of secondhand embarrassment for the owner.

Saturn Sky

This one kinda hurts because… on paper, it’s not terrible? It was a small, rear-wheel-drive roadster, a competitor to the Mazda Miata. And it looked pretty sharp, very angular and modern. But… the build quality. Oh, the build quality. The interior felt like it was made from recycled yogurt cups, and things would just… rattle. And creak. The reliability was a real gamble. So you’d get this sporty car for around $27,000, but you’d spend the whole time waiting for something to fall off. It had potential, but it just didn’t stick the landing.

Ford Mustang Convertible (base model, circa 2005-2010)

Okay, don’t get me wrong, I love a Mustang. But the base model V6 convertible from that era? It was… a poseur’s car. It looked the part, sure, with the top down. But it had all the body rigidity of a wet noodle. You’d go over a railroad track and the whole car would shimmy for like, five seconds after. And the engine was so underwhelming—all the noise, not much of the go. You were paying for the image, which was like $28,000, but you were missing the soul of what makes a Mustang great. It was all hat, no cattle, as they say.

Fiat 500c

It’s so cute, right? It’s adorable! The little roll-back fabric roof is charming. But… it’s a Fiat. And I say that with a sigh. The reliability on these is just legendary, and not in a good way. Electrical gremlins, weird mechanical issues… you’re basically signing up for a quirky, high-maintenance pet, not a car. And it’s so tiny and slow, you feel vulnerable everywhere. For about $20,000, you get a whole lot of anxiety bundled with your Italian charm. It’s a “fun weekend car” that quickly becomes a “why won’t you start on a Tuesday morning” car.

BMW 3 Series Convertible (E36 generation)

Okay, a BMW! This should be good, right? And it was, when it was new and tight. But these are old now. And an old German convertible is a… a money pit. The power tops are complicated, the hydraulic cylinders fail, the windows get out of sync… it’s a nightmare. You could buy one for, I don’t know, $5,000 now, but you’d be sinking another $10,000 into it just to keep the roof working and the check engine light off. It’s a beautiful driving experience when it works, but it’s a heartbreak on wheels.

Volkswagen Eos

This one seemed like a great idea. A cute VW coupe with a fancy, complex retractable hardtop. It gave you a sunroof and a convertible all in one! But all that complexity… it was a reliability disaster waiting to happen. The mechanisms for that roof were famously expensive to fix when—not if, when—they broke. And it was kinda heavy, so it wasn’t even that fun to drive. You’d pay over $30,000 for this sophisticated German engineering, and then get a repair bill that would make you cry. It was too clever for its own good.

Mitsubishi Eclipse Spyder (3rd gen)

The Eclipse Spyder… ugh. It was based on the coupe, which was already front-wheel drive and not exactly a sports car legend. Chopping the roof off made it even more… floppy. It was soft, it understeered like crazy, and the 4-cylinder engine was just… blah. It was a car that tried to be sporty but had no real sporting credentials. For around $26,000, you got a car that looked fast but drove like a sofa. It was all show, and the show wasn’t even that great.

Cadillac Cimarron

Oh, the Cimarron. This is the king, the godfather of automotive regret. It was basically a Chevy Cavalier—a cheap, boring economy car—with a Cadillac badge and a leather interior slapped on. And they made a convertible version? It was a cynical, blatant attempt to trick people into thinking they were buying a luxury car. It drove like a Cavalier, it broke like a Cavalier, but it cost like a Cadillac. It was probably, like, $15,000 in the 80s, which was a lot! It was an insult, honestly. Just a complete and total con job on four wheels.