These 20 Cars Were Cool 20 Years Ago… Unfortunately, They Didn't Age Well

Jul 19, 2023

Some car designs are incredible and can span decades, retaining a desirability years later, but some classic cars lose their looks more quickly.

Many cars get branded as being cool upon release. Whether they stay cool, is another matter. Classic cars like the Mk1 Audi TT and the gorgeous Alfa Romeo Brera caused a stir when they broke cover. Exciting designs that garnered admiration and created dream cars for some. To their credit, both still look pretty fresh today.

Other cars aren't so lucky. Their bold styling may bring about initial praise, but it is short-lived. What is once deemed cutting-edge gets stamped as being out of date. Despite their best efforts, several of these used cars end up being a shadow of what they once were. They are the 'in thing' for a short time and then discarded. Destined to become the automotive equivalent of parachute pants.

Vehicular fashion is a curious thing. There are many fads and many passing trends. Some designs stick and become instant classics, while some burn bright and fast before fizzling out. These cars were cool 20 years ago, but unfortunately, they didn't age well at all.

Updated April 2023: While some cars age like fine wine, others end up as bargains nobody is proud to show off anymore. We've updated this list with more cars that have completely gone out of style or become obsolete in 2023.

The Dodge Stratus is a great-looking midsize car that's fun to drive. Sadly, having these qualities doesn't mean a car will be dependable, and that was the issue with the Dodge Stratus, which suffers from poor build quality.

This car had several issues, ranging from bad front and lower ball joints to whining and other noises when shifting gears, failing automatic transmission, defective crankshaft sensor, and oil leaks.

When the second-generation Chrysler Concorde launched for the 1998 model year, reviewers hailed its attractive styling, calling it revolutionary and a reinterpretation of the modern sedan. Giving credit where credit is due, the Concorde was arguably the best-looking car you could buy at the time and still looks great even by today's standards. Its bespoke, Aston Martin-like design featured clean and simple lines that looked exotic and intriguing, imbuing it with a ravishing beauty that's hard to ignore.

Unfortunately, a mountain of problems soon caused many to shun this car. The vehicle suffered from oil sludge problems that led to engine failure, transmission troubles, stuck windows that won't go up or down, as well as paint job issues.

The Cadillac Catera entered the market with the pretensions of being a luxury sedan, with a launch promotion hailing it as "the Caddy that zigs." Sadly, this Caddy failed to live up to its promise, and myriads of problems meant it wouldn't live long enough to redeem itself.

Uninspiring performance, costly repair and maintenance costs, failing timing belt tensioner pulley, electrical system problems, and engine cooling failures meant this Opel Omega B-based sedan failed in its mission to become the first successful entry-level sedan built by a U.S. automaker.

The second-generation Dodge Intrepid is yet another sedan that slipped into irrelevance due to unreliability. One commonly reported problem was that the transmission often failed to shift out of Park. The Intrepid was also subject to random holes and cracks in the dashboard, as well as damaging oil sludge buildup that resulted in engine failure.

Related: How Reliable Is A 2015 Mercedes-Benz CLS 63 AMG

The Amanti was Kia's first premium car, and as such, it aspired to the sophistication of Mercedes-Benz. But while it had the look of a Mercedes-Benz on the outside, its interior lacked the luxury and premium quality of Mercedes-Benz. In addition, its soggy suspension resulted in poor ride and handling characteristics to the extent it was at risk of tipping over when taken too fast around corners. These, as well as a failing accelerator position switch, engine immobilizer problems, and bad AC compressor clutch, meant that doubts about the Amanti quickly replaced excitement.

A funky-looking coupe with a cool name, the Pontiac Sunfire featured exciting styling, as well as a plethora of sports additions like the rear spoiler and deep front valance. It also had a zingy 2.4-liter engine with 150 hp. Good for hitting 60 mph in 8.8 seconds. It was a cost-effective little car. Praised for its economical approach to motoring, the Sunfire was warmly received. But that bold statement styling soon became outdated. No one wanted three-spoke alloys and a mini spoiler. The Sunfire faded from the limelight to become a has-been. It's one of the cars that led to Pontiac's early grave.

One of the automotive world's boldest creations. A French-backed supercar with a bonkers engine made mostly from German parts. The Bugatti Veyron dished out impressive statistics with reckless abandon. A record-breaking supercar with a price tag that dropped jaws.

While the Bugatti Veyron still has blinding statistics, it looks to have faded. The front grille piece is ghastly. Painted with a two-tone finish, it looks like a cheaply finished kit car. What was once deemed flamboyant, now looks overblown and ridiculous. Time has not been kind to it.

It had an engine to get gearheads' tongues wagging. A screaming 2.0-liter supercharged unit with 205 hp capable of propelling the Cobalt SS to 60 mph in 6.1 seconds. The Cobalt SS was very fast and offered great fun. It ticked all the boxes, and many bought into the hype.

The only thing the Cobalt SS lacked was any lasting appeal. The exterior looked okay. It sat between being plain and interesting. But today, it just stands as boring. Too sophisticated for its own good, the Chevrolet Cobalt SS lost out to more powerful, yet basic machines.

Dripping with graceful prowess. The Rolls-Royce Phantom is for those that want to waft around in luxury while making sure everyone they pass knows that they are wealthy. A statement of superiority, it did the business, pushing luxury motoring to new heights. While it set new standards, it did so with a foot firmly in the past. Trading off aged influences hasn't done the Phantom any favors. From all angles, it now looks older than it is. A retro-styled lurching behemoth, and a tacky reminder that the super wealthy can't buy street cred.

Related: Here's Why The Rolls-Royce 6.75-Liter V12 Engine Is A Work Of Art

The world went crazy for the fifth-generation Mustang. It grabbed the whole retro vibe and ran through the halls screaming with it. At the time, it looked fantastic, it was a modern Mustang with a distinctive old-school Mustang look. A fitting shout-out to its ancestry and roots.

These days it looks bloated and heavy. A Mustang that has been dining daily at the all-you-can-eat buffet. Those cool retro touches now look like dreadful aftermarket additions. This generation Mustang will likely have its time again, but it will need to wait another 20 years.

A sedan that thinks it's a coupe, Mercedes-Benz knocked it out of the park with the CLS. A super comfortable vehicle with plenty of appeal. It broke the mold back when sedans and coupes were a thing. Blending two best-selling vehicle classes into one, buyers couldn't resist.

The thorn in the side of the CLS was the march of the SUV. Sedans and coupes fell out of fashion, leaving the CLS floundering. Once a beauty queen, it's now an unwanted land barge. A mess of outdated design cues, the CLS got left behind in an evolving market.

A hand-built special, the Spyker C8 was an explosion of wild ideas crammed into one place. It was refreshing at the time, a shining beacon of creativity with acres of leather, machined metals, and body vents. It also had 395 hp from a 4.2-liter V8, albeit an Audi engine.

The problem with the boutique design is that it runs the risk of looking silly, very quickly. The Spyker C8 was muscular and aggressive back then. Today, it looks fussy. There's too much going on. It's like a kid has designed their ultimate fantasy car, and then Spyker made it.

Small, light, and only available as a drop-top, the heavily redesigned Toyota MR2 moved into a whole new sphere. It was a superb handling car, a high-revving little sports car. Proving to be frugal too, it offered superb value for money and gained a cult following.

The MR2 Spyder is available for peanuts. That goes to show how far from grace it has fallen. Resembling a poor kit car version of a Porsche Boxster, the MR2 Spyder is an ugly little car. Less characterful than the one it replaced, it lacks charisma and any classic appeal.

Related: Find Out How To Shove A Camry Engine Into A Toyota MR2

The Ford Thunderbird cashed in on the popular retro vibe. Classy and sleek, with a rear porthole window, it reincarnated a much-loved model. Ford dropped a 4.0-liter V8 into an eye-catching body, giving the Thunderbird a generous 280 hp, thereby providing plenty of performance.

Just look at it. Polished chrome wheels, a dreadful gaping front grille, that ridiculous hood intake, plus a pair of porthole rear windows. It's the car that has good taste bypassed. The last Ford Thunderbird is a perfect example of why some retro ideas needn't ever get made – or sold.

Getting noticed in a packed market is a hard task. The first-generation Cadillac CTS managed to do this by being radically different. Its angular looks and apparel get the curb appeal. Well-equipped and with a host of engine options, there was something for everyone. From a distance, it looks like a car made from Lego. The front and rear lights are mostly to blame, along with the razor-sharp body lines. Too boxy for its own good, all those little stand-out finishes that made the CTS unique now work against it. Also, the interior is just as bad.

The W140 generation of the legendary S-Class is one of the greatest full-size luxury sedans of all time, which is why its successor – the W220 – had such huge shoes to fill when it debuted at the turn of the century. The W220 impressed many at first as it had a sleeker and more modern design than the W140 and had some of the most advanced technologies at the time.

Unfortunately, the W220's technological advancements later became its downfall, as it was a nightmare to maintain.

Cadillac has always wanted to develop a sports car that would help it compete with foreign options. So in the early 2000s, Cadillac decided to build a more luxurious version of the popular Corvette and slap a much higher price tag on it. The result was the XLR.

The XLR used the same platform as the C6 Corvette but had a new design that admittedly looked great and a more upscale interior with features like wood trim and heated seats. Unfortunately, the XLR made less horsepower than the C6 Corvette despite weighing a lot more, which led to unacceptable performance for a $75,000 car. It's no surprise that Hagerty values the XLR at just $21,000 despite its rarity.

RELATED: 10 Sports Cars That Didn't Age Well At All

The Hummer H2 picked up right where its military predecessor – the H1– had left off when it debuted in 2002, but since it was more of a luxury SUV than the H1, it received a lot more hype. The H2 was among the most popular SUVs in the 2000s thanks to its imposing size, luxury features, and overall presence. Every celebrity and professional athlete seemed to own one just to show off.

However, it didn't take long for people to notice the H2's biggest problem – fuel efficiency, or lack thereof. The H2 offered a dismal 10 mpg thanks to its thirsty 6.2-liter V8, making it hard to live with even for the wealthiest of individuals. In today's eco-conscious world, where fuel efficiency is on top of many people's lists of priorities, the H2 cannot survive.

The iconic Mercedes-Benz SL is one of the longest-running models in history, as its story started in the '50s. There have been multiple generations of the SL since its introduction, and the R129 is among the best. The R129 helped Mercedes-Benz earn its reputation for building technologically advanced and over-engineered sports cars, as it was easily among the best '90s sports cars.

The R129's successor – the R230 – wasn't as good, especially in terms of reliability. The R230 is the true definition of a money pit, especially if it's one of those V12-powered models. Some owners went as far as warning other people to steer clear of the R230 due to how much of a nightmare it can be.

When Ford bought Aston Martin, it quickly started developing a new entry-level model that would give more people access to the prestigious brand and help the company make more money. The result was the DB7, and the strategy worked so well that the DB7 became the best-selling Aston Martin model ever at the time.

While the DB7 was a bargain back in the '90s and still is today in the used market, it's not a great car to buy, especially if you want to drive it. The DB7's main problem is that it used the Jaguar XJS platform, which was already 20 years old in 1990. We've covered some of the DB7's reliability issues in the past, and they explain why it's among the cheapest V12-powered sports cars in the market.

Having cut his teeth on the UK street racing scene in the late 90's and early 00's RJ faded from the limelight only to return 20 years later. An avid motoring enthusiast RJ especially enjoys JDM and Italian cars, and is an experienced multi-industry writer.