Recently we talked about Toyota’s FJ Cruiser and its place in the retro styling craze that was sweeping America at the turn of the 21st centurty. Besides the FJ, you had the VW New Beetle, the Mini Cooper, Ford Thunderbird, and others. All cars that looked like they teleported from a long-ago decade, but with modern technology and powertrains.

But two cars from an unlikely source—Chrysler Corporation (now Stellantis)—were truly at the leading edge of the retro car movement. Viewed through the lens of today, where half the cars on the road look like an egg, it’s hard to believe that either one got the green light for production.

The Plymouth Prowler came before the PT Cruiser

After producing boring and relatively crappy K-cars throughout the ’80s, Chrysler stunned the world with its V10-powered Viper roadster in 1992. Fresh off that success, the same designer, Tom Gale, penned another wild creation—one that would make the Viper seem downright tame by comparison. At least in the looks department, that is. It was the 1997 Plymouth Prowler, a two-seater convertible.

The Prowler was designed to look like the homebuilt hot rods from 1950s, which were constructed from even older cars like the 1932 Ford “Deuce Coupe.” The key words in that sentence being “look like.” Plymouth’s factory hot rod is often derided by gearheads for being all show and no go. Indeed, its mild V6 engine was lifted straight from a Dodge Intrepid sedan.

Besides lacking a V8 engine, the Prowler also lacked the option for a manual transmission transaxle. Still, the Prowler’s extensive use of aluminum made it very light and the V6/automatic combo actually gave decent performance. Per a MotorTrend test, zero to 60 took 7.1 seconds on its way to a 15.3 second standing quarter-mile.

As unconventional as it was, the Prowler still had to make some concessions to be street legal, including a pair of motorcycle-esque front fenders that steered in tandem with the front wheels. Since the trunk was both tiny and tasked with holding the lowered convertible top, a matching cargo trailer for the Prowler was available as a factory accessory. In 2001, Plymouth ceased to exist, so the last round of Prowlers were sold by Chrysler.

The PT Cruiser looks like a bulkier cousin of the Plymouth Prowler

Even though the Plymouth Prowler wasn’t a huge sales success, it created a ton of hype and publicity for Chrysler, which was positioning itself as a youthful, sporty brand. To that end, Chrysler engineers developed another retro vehicle, this one with far more practicality than the Prowler.

A pair of concept cars debuted in the late 1990s, alternately called the Plymouth Pronto and the Pronto Cruizer, which would morph into the production PT Cruiser for the 2001 model year.

Based on a heavily reworked Dodge Neon front-wheel drive platform, the PT Cruiser defied classification. Was it a mini-minivan? A hatchback? An SUV? In the eyes of the EPA, it was technically classified as a truck, reportedly because the fuel economy standards were more lax for trucks.

Under the hood was a thoroughly lame 2.4-liter four-cylinder with 150 horsepower, coupled to the buyers choice of automatic or manual transmission. To be fair, the PT Cruiser did gain some performance as the years passed, including a turbocharged GT version that peaked at 230 horsepower. For the 2005 model year, the PT got a two-door convertible variant with a Volkswagen Cabriolet-esque basket handle roll bar.

There’s an Oscar Wilde quote that says “imitation is the sincerest form of flattery.” Well, the PT Cruiser was feeling mightly flattered when Chevy launched a near-identical vehicle called the HHR (Heritage High Roof) for 2006. Some automotive jounalists felt that the HHR was a better execution of the concept, but there’s no denying that Chevy shamelessly cribbed the idea from Chrysler.

Under the new ownership of Cerberus Capital Management, Chrysler announced that 2010 would be the last year for one of the most successful retro cars. In total, more than 1.3 million PTs were sold worldwide.

Which weird car is the weirdest?

Without question, the Plymouth Prowler was the weirder vehicle between Chrysler Corp’s two time machines. It was the answer to a question that nobody asked.

It wasn’t fast enough to back up its tough looks, the trunk space was nonexistent, and so was visibility. With the convertible top raised, blind spots the size of Texas emerged. Still, the Prowler is one the most daring cars ever to roll off a mass-production assembly line. Even 20+ years later, its styling still looks fresh and unique.

Being the very definition of niche, less than 12,000 units were sold during the Prowler’s entire five year lifespan. For such a rare car, the Prowler is still an affordable indulgence nowadays. According to the valuation site classic.com, the average transaction price among 51 vehicles sold in the past 12 months is $33,317. The matching trailer for hauling your groceries isn’t included, though.