Home Cars 20 Times Automakers Tried to Be Cool… and Totally Missed
Cars

20 Times Automakers Tried to Be Cool… and Totally Missed

Cameron Eittreim June 29, 2025

Automakers have always chased the elusive idea of “cool.” Sometimes, those bold moves lead to iconic cars that define generations. But other times, the quest for trendsetting style or innovation goes spectacularly wrong.
Instead of earning street cred, these vehicles become infamous for their awkward looks, odd features, or baffling concepts.
In this article, we’ll take a joyride through twenty unforgettable moments when carmakers tried to make a splash—only to end up stalling at the side of the road.

1. Pontiac Aztek

Pontiac Aztek 1112 21
A Pontiac Aztek SUV sits parked on the street, showcasing its infamously awkward lines and controversial design. | Photo by Abhinav Joshi on Pexels

The Pontiac Aztek was supposed to be a bold step into the future of SUV design. Instead, its boxy shape and mismatched angles left drivers scratching their heads.
What GM hoped would be a trendsetting vehicle quickly became a pop culture punchline, regularly topping lists of the world’s ugliest cars.
Despite its practical features, the Aztek’s appearance overshadowed everything else, making it a cautionary tale for automakers eager to stand out. Source: MotorTrend

2. Chrysler PT Cruiser Convertible

Chrysler Pt Cruiser Convertible 2177 60
A bright red Chrysler PT Cruiser Convertible with its top down, showcasing retro styling often cited among convertible flops. | Photo by Efrem Efre on Pexels

Chrysler aimed to capture nostalgia and fun with the PT Cruiser Convertible, hoping its retro lines and drop-top design would charm drivers.
Unfortunately, the final product drew criticism for its odd proportions—especially with the roof down—and left many wondering if style had trumped substance.
Performance was underwhelming, and the car’s looks didn’t age well, making it a frequent target for mockery rather than admiration. Source: Car and Driver

3. Nissan Juke

960px nissan juke 16gt four type v
The Nissan Juke stands out with its quirky, unconventional design, turning heads as a bold compact SUV. | Photo by Toms Svilans on Pexels

The Nissan Juke burst onto the scene with a style that was anything but ordinary.
Its bug-eyed headlights and unusual curves were intended to make a statement, but instead, they left many scratching their heads.
While some admired its boldness, the majority found the Juke’s look too quirky—bordering on bizarre. This polarizing design divided critics and buyers alike, ensuring the Juke would be remembered more for its looks than its driving experience. Source: Top Gear

4. Lincoln Blackwood

2002 Lincoln Blackwood
A sleek Lincoln Blackwood luxury pickup showcases its unique fully carpeted truck bed, blending comfort with utility. | Photo by Abdulwahab Alawadhi on Pexels

The Lincoln Blackwood set out to blend luxury and utility, but the execution left both truck fans and luxury buyers puzzled.
A plush, carpeted truck bed made hauling anything but pillows risky, while the exterior styling tried—and failed—to look upscale.
This strange hybrid didn’t satisfy either market, and its short-lived run quickly cemented the Blackwood’s reputation as a misfire. Source: The Drive

5. Subaru Baja

Subaru baja photo 6333 s original
A quirky Subaru Baja car-pickup hybrid stands out, representing one of the most memorable failed car designs. | Photo by Alex   on Pexels

The Subaru Baja tried to carve out a niche by fusing sedan comfort with pickup utility.
Unfortunately, this odd mashup left buyers scratching their heads. The Baja’s small bed limited its usefulness as a truck, and its quirky styling didn’t woo sedan lovers either.
Instead of capturing two markets, it missed both, quickly earning a cult following for its weirdness but struggling to find widespread appeal. Source: Jalopnik

6. Chevrolet SSR

03ssr 03sigssr
2003 Chevrolet SSR Signature Series. (X03CT_SR054)

The Chevrolet SSR aimed to turn heads with its blend of retro truck looks and a slick retractable hardtop.
However, the end result was a vehicle with a confused identity—neither a true sports car nor a practical truck.
Buyers were unsure what to make of it, and sales quickly fizzled. Despite its bold styling, the SSR is now remembered as a curious misstep in Chevrolet’s lineup. Source: Hagerty

7. Smart ForTwo Cabrio Brabus

1280px Smart Ev Jeremy Scott 2012 La Show
A sleek Smart ForTwo Brabus convertible shows off its sporty flair, proving tiny city cars can be thrilling. | Photo by Julian Largo on Pexels

Brabus set out to inject excitement into the petite Smart ForTwo Cabrio, promising sporty dynamics in a tiny package.
The result, however, was underwhelming. The price soared, but real-world performance barely budged.
Buyers were left wondering who this car was really for, as it failed to deliver meaningful thrills or practical value. Source: Auto Express

8. Plymouth Prowler

1200px plymouth prowler %289497066681%29
A bright purple Plymouth Prowler stands out among classic hot rods, showcasing retro flair despite its infamous flop status. | Photo by Juliano Couto on Pexels

The Plymouth Prowler arrived with wild, hot-rod-inspired styling—open wheels, swooping fenders, and all the attitude you could want.
Unfortunately, the excitement faded once enthusiasts learned it only packed a modest V6 under the hood.
For all its eye-catching looks, the Prowler just didn’t have the muscle to back up its appearance, leaving many fans feeling let down. Source: Car and Driver

9. Cadillac Cimarron

1200px 1988 cadillac cimarron in bluish silver%2c front right
1G6JG51W1JJ504703

Cadillac tried to win over younger drivers with the Cimarron, but the plan quickly backfired.
Essentially a dressed-up Chevy Cavalier, the Cimarron lacked the luxury, performance, and refinement expected from America’s premier luxury brand.
The move didn’t just fail to attract new customers—it also damaged Cadillac’s reputation for years to come, serving as a classic example of misguided badge engineering. Source: Autoweek

10. Honda Element

Honda Element Ex Photo 6393 S Original
A bright Honda Element, with its signature boxy shape, stands out among other trendy youth market cars. | Photo by John Rae Cayabyab on Pexels

The Honda Element was crafted to appeal to active, outdoorsy youth, boasting modular seating and easy-clean interiors.
Yet, its boxy, utilitarian styling turned off many buyers who found it more awkward than adventurous.
While it won over a handful of fans for its practicality, the Element never achieved the cool, aspirational image Honda intended. It remains a quirky outlier in the brand’s history. Source: Road & Track

11. Toyota FJ Cruiser

Used 2014 toyota fj cruiser
A bold Toyota FJ Cruiser stands ready for adventure, its retro SUV design highlighting its off-road capabilities. | Photo by Twilight Kenya on Pexels

The Toyota FJ Cruiser took a bold gamble with its retro-inspired design, channeling the original FJ40’s rugged spirit.
While off-roaders loved its capability, the quirky styling, poor rear visibility, and awkward rear-hinged doors made it impractical for everyday families.
The FJ Cruiser’s appeal proved too niche for mainstream buyers, leading to its discontinuation despite a loyal following. Source: MotorTrend

12. Volkswagen New Beetle Dune

Img 3549
The Volkswagen Beetle Dune stands bold among off-road cars, showcasing its adventurous spirit alongside other unique beetle variants. | Photo by Connor McManus on Pexels

Volkswagen attempted to toughen up the friendly New Beetle with the Dune edition, adding raised suspension and rugged styling cues.
However, the off-road-inspired look didn’t bring real capability, leaving buyers scratching their heads at its purpose.
Instead of winning over adventure enthusiasts, the Dune mostly confused consumers and faded quickly from memory. Source: Autoblog

13. Hummer H2 SUT

Used 2006 hummer h2 sut
A massive Hummer H2 SUT dominates the scene, showcasing the bold and excessive side of modern pickup trucks. | Photo by Liam Moore on Pexels

The Hummer H2 SUT aimed to combine brute-force style with pickup versatility, but its massive size and terrible fuel economy quickly drew ire.
While it looked undeniably tough, few needed such excess, and critics slammed its inefficiency and impracticality.
The H2 SUT soon became a symbol of automotive overindulgence rather than cool innovation. Source: The New York Times

14. Jeep Compass (First Generation)

2007 Jeep Compass Sport 4x4 Pic 4708992611360782265 1600x1200 1
A silver Jeep Compass, Jeep’s compact SUV, sits parked under cloudy skies, its design hinting at lost potential. | Photo by ahmad syahrir on Pexels

The first-generation Jeep Compass was Jeep’s play for urban style and crossover convenience.
Unfortunately, it missed the mark with bland, uninspired looks and subpar off-road performance for the brand.
Neither rugged enough for Jeep loyalists nor stylish enough for city drivers, the original Compass quickly faded into the background. Source: Edmunds

15. Fiat Multipla

Photo Credit: Motor 1

The Fiat Multipla was engineered to break the mold, offering a unique, ultra-practical six-seat layout in a compact package.
But its bulbous, double-decker styling drew gasps and giggles rather than admiration.
Despite winning praise for its clever interior, the Multipla’s unconventional looks made it a punchline across the globe, regularly topping “ugliest car” lists. Standing out isn’t always a good thing in the car world. Source: Top Gear

16. Chevrolet HHR Panel

2009 Chevrolet Hhr Ss Panel Pic 4086190767502221610
A retro-inspired Chevrolet HHR Panel van stands parked, showcasing its unique blend of classic styling and modern utility. | Photo by Erik Mclean on Pexels

The Chevrolet HHR Panel tried to channel vintage delivery van vibes, ditching rear windows for a commercial look.
Unfortunately, its retro-inspired styling confused buyers and failed to generate excitement.
The HHR Panel never found a real audience, missing the mark on both utility and cool factor. Source: The Truth About Cars

17. Scion xB (Second Generation)

Scion xb 2004 5
A bold Scion xB showcases its iconic boxy design, highlighting the unique style of Scion vehicles. | Photo by Pixabay on Pexels

The original Scion xB built a cult following with its quirky, boxy shape and youthful vibe.
But when the second generation debuted, it abandoned those sharp lines for a heavier, more generic look.
The result? It lost its unique appeal and alienated the very buyers Scion wanted most. The once-edgy xB became just another bland compact, missing the mark on cool entirely. Source: Jalopnik

18. Mercedes-Benz R-Class

Mercedes benz r class
A sleek Mercedes-Benz R-Class luxury minivan stands parked, embodying ambition but remembered as one of Mercedes’ rare flops. | Photo by Ishan Kulshrestha on Pexels

The Mercedes-Benz R-Class set out to redefine family transport by mixing minivan versatility with German luxury.
But its unclear identity—neither a true SUV nor a classic minivan—left buyers bewildered.
Sales lagged, and the R-Class quietly exited the stage, remembered more for its confusion than its comfort. Source: Car and Driver

19. Ford Thunderbird (2002 Revival)

2002 Ford Thunderbird22
A sleek Ford Thunderbird sits parked under neon lights, embodying retro charm despite its short-lived revival. | Photo by Ollie Craig on Pexels

The 2002 revival of the Ford Thunderbird banked on nostalgia, reviving classic lines and convertible charm.
However, the modern T-Bird lacked the spirited performance and excitement of its forebears, leaving many buyers underwhelmed.
While it looked the part, it drove like a soft cruiser rather than an icon reborn, leading to sluggish sales and a short production run. Source: Hemmings

20. BMW i3

1200px toulousaine de l%27automobile 7441 bmw i3
A sleek BMW i3 electric car glides through vibrant city streets, blending modern design with eco-friendly innovation. | Photo by Pixa Pexel on Pexels

BMW’s i3 set out to revolutionize city driving with its futuristic design and electric powertrain.
While undeniably innovative, its unconventional looks, compact size, and premium price tag left most buyers cold.
Despite cutting-edge technology and eco-cred, the i3 struggled to achieve mainstream coolness, remaining a niche curiosity rather than a trendsetter. Source: The Verge

Final Thoughts on the Quest for Cool

1200px D%c3%bclmen%2c Gewerbepark %22st. Barbara%22%2c Bmw I3 2019 7495
A sleek lineup of futuristic concept cars turns heads in a bustling showroom, drawing excited reactions from the crowd. | Photo by enes çimen on Pexels

As these twenty examples show, even the biggest names in the auto industry can misjudge what’s truly cool.
Chasing trends or taking bold risks doesn’t always lead to automotive greatness—sometimes, it results in vehicles that are more memorable for their missteps than their innovation.
But there’s a lesson here: pushing boundaries is essential, even if the results miss the mark.
Which infamous car flop do you remember most? Share your thoughts and keep the conversation rolling!

.article-content-img img { width: 100% }
Advertisement
Please wait 5 sec.