There aren’t too many new cars you can get for under $20,000. True, there are some well-reviewed models, like the Toyota Yaris, Kia Soul, and Honda Fit, that start for less. But these often base-trim cars don’t exactly rank high in terms of cool factor. Luckily, the used market offers a way to get fun performance and cool design at an affordable price. And one of the coolest sub-$20,000 cars you can buy is the Porsche Cayman.

Other cars we considered

To be sure, as with many aspects of vehicle design, ‘coolness’ tends to be subjective. What one person likes isn’t always what another person likes. And if cheap performance is the goal, there are a lot of other used cars that fit that criteria apart from the Porsche Cayman.

The hot hatch segment alone has multiple entries. There’s the Fiat 500 Abarth, Ford Fiesta ST and Focus ST, Volkswagen GTI, and Honda Civic Si. And if you’re into JDM, there’s the AWD Nissan Pulsar GTi-R and Autozam AZ-1.

Road & Track recommends the E46 BMW M3 and the 996-gen Porsche 911. You can also get a very well-kept Mazda Miata for $20k, as well as a Honda S2000. Then there’s the Toyota 86, Subaru WRX, or one of the last rotaries made, the Mazda RX-8. You can also get a Camaro SS for under $20k, and it’s a genuine BMW competitor. Basically, the used buyer isn’t lacking for choice.

So, to narrow down the field, several criteria were considered.

The ‘coolest car’ criteria

First, the coolest car had to be a passenger car. Thus, while the Isuzu Vehicross is definitely rad, it’s an SUV and doesn’t qualify. Ditto the Suzuki Samurai/Jimny.

Second, the car had to be fun to drive while also offering street appeal. Thus, although JDM vehicles like the Pulsar, Celica GT4, and Toyota Century are interesting, you’d likely have to explain what makes them interesting. And while the VW GTI is a fun car, it’s also designed to blend in—you’ll rarely see anyone turn to look back at it.

Third, the coolest used car had to be free of major faults, or at least have repairable faults. This actually kept the 996 in contention. Yes, it has the infamous IMS issue, but there are retrofit kits which fix it.

Finally, the car had to have reasonable maintenance costs. Obviously, a BMW will have higher maintenance costs than a Camaro, simply due to the original price difference. However, Bimmer Forums and E46 forum users, CarThrottle, and R&T note that the E46 M3 is noted to have particularly high running costs. Even more so, based on Rennlist and FlatSixes reports, than the 996 911, and in line with noted problem-child E60 M5. And while the RX-8 isn’t necessarily as unreliable as many think, rotary engines still have their unique foibles.

So, based on these criteria, after looking through all the information, the coolest under-$20k car is the Porsche Cayman.

Why the Porsche Cayman is the coolest used car

The first Porsche Cayman, the 987, debuted in 2006 in S trim, the PCA Cayman Register reports. It came with a 3.4-liter flat-six, with 295 hp and 251 lb-ft, linked to a 6-speed manual or 5-speed automatic. The base Cayman joined in 2007, with a 2.7-liter flat-six, which made 245 hp and 201 lb-ft, and a standard 5-speed manual.  

In 2009, the Porsche Cayman received a redesign and updated engines. The base car now got a 265-hp 2.9-liter flat-six. The S still used a 3.4-liter engine, but output was increased to 315 hp. The Cayman’s automatic changed to the 7-speed PDK dual-clutch transmission, widely considered one of the best on the market.

While the Porsche Cayman isn’t necessarily fast in a straight line, the mid-engine sports car was never about 0-60 times. Instead, it’s on a curvy road that this car shines, Jalopnik reports, especially with its communicative hydraulic steering. The Cayman rides on the same platform as the Boxster, though the Boxster actually came first. However, WhatCar reports the Cayman has sportier suspension and is more rigid due to its fixed roof. Basically, think of the Cayman as a more powerful, upscale Miata, but with even better handling.

In addition, although the 911 tends to get most of the glory, Autocar reports it’s the Cayman that’s arguably more fun on a normal road. It’s also cheaper to maintain, even compared to the less-expensive 996, according to Rennlist. Plus, while design is always subjective, Good Car Bad Car reports the Cayman is actually rarer than the 911. Even before the rise of the air-cooled 911, the Cayman stood out.

In addition, though it only has 2 seats, the Porsche Cayman is a reasonably-good daily-driver. It has 2 luggage compartments, and the ride is fairly compliant.

What to look for before you buy

It is possible to find a face-lifted 987 Porsche Cayman—aka the ‘Gen 2’—for under $20k, BaT reports. However, it’s more common to find a 2006-2008 example for that money. And there are some issues to be aware of.

For one, like the 996 and some 997 911s, Revolution Porsche reports the 2006-2008 Cayman also has the IMS issue. If the intermediate-shaft bearing fails, the entire engine needs to be replaced. However, both Rennlist and Porsche owner forum users report the IMS is often blown out of proportion. Especially with the Cayman, IMS failure is fairly rare. Also, many early 987 cars have already had the problematic part replaced.

In addition, PistonHeads reports that 2006 Caymans have suffered bore scoring on their piston walls. The tell-tale sign is excessive smoke from the tailpipe, as the scoring causes the engine to burn oil. That’s why, whenever you buy a used car, it’s recommended you get an independent inspection from a trusted mechanic.

There’s also one other known issue that affects the Porsche Cayman, as well as 987 Boxster, and the 996 and 997 911, Revolution Porsche reports. The rear main seal, AW Motorsport explains, keeps engine oil from leaking into the transmission. However, the RMS can fail and start to leak over time to a design flaw.

However, this isn’t actually detrimental to the car. At worst, this will lead to some oil on your driveway. The RMS can be replaced with a newer version, but the procedure requires removing the transmission. Unless you can’t stand the oil drip, it’s recommended not to replace it until you have to replace the clutch. And if you find a 2009 or later model, these don’t have the problematic RMS at all.

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