Chrysler is one of the ‘Big Three’ American automobile manufacturers, which recently became a subsidiary of Stellantis – now the world’s sixth-largest automaker. Established in 1925, the Chrysler Corporation soon became the third best-selling car manufacturer in North America, just behind Ford and General Motors, a title it held onto until 1949.
Throughout its somewhat turbulent history, Chrysler has produced some great cars, like the Imperial Crown and the 300C SRT – and some truly terrible cars also, like the TC by Maserati and the Crossfire. Whether good or bad, they have become legendary in their respective classes and many of them are still relevant and sought-after today.
Here is a list of some of the most influential, important, and beautiful Chrysler cars currently for sale in the second-hand car market – even if some of the design and engineering were borrowed from some of their competitors.
8 1997-2002 Chrysler Prowler
The Chrysler Prowler is a wholly fascinating car. It is a mish-mash of various Chrysler, Dodge, and Jeep parts adding up to a disappointing result. It is fitted with the 3.5-liter V6 out of a Chrysler 300M, mated to a 4-speed automatic from the Dodge Intrepid.
The only redeeming factor about the Prowler was the way the exterior looked. It was a factory-built car, which equaled a modern take on a 1940s hot-rod – bar the performance. It would have been redeemable if Chrysler put a V8 in it, but the Prowler was discontinued before anything like that could occur. Still, it is a cool-looking car and is definitely one of the best – if not most interesting, used Chryslers to buy.
7 1996-2000 Chrysler Voyager
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The fourth-generation Chrysler Voyager was the minivan that built on the success of the previous generation, to become the go-to choice for anyone wanting a relatively premium, relatively inexpensive family hauler. It was fitted with various engines throughout its life, including specific ones for specific territories.
The North American Voyager (later renamed to the Town & Country) featured a range of gasoline engines, with the base spec being the 2.4-liter i4, producing 150 hp and 165 lb-ft of torque. The Voyager was not quick, but it was good at being a minivan – with clever seating solutions and lots of space inside – which made it one of the best Chryslers on sale. These days, a used Chrysler Voyager is available for as little as $2,500.
6 2014-2016 Chrysler 200C
The 200C was a more compact car than the larger 300, based on the Alfa Romeo Giulietta and Dodge Dart platform. Unlike with the Giulietta and Dart, the 200C was available with the 3.6-liter Pentastar V6. The 200C was the replacement for the Sebring sedan and featured a 9-speed automatic transmission as standard.
While not as instantly noticeable as a 300C, the 200C is still a good-looking car with a good amount of features, powerful enough engines for its class, and optional all-wheel-drive. The 200C is available on the used car market for around $10,000, with some even dipping below that number.
5 1969-1973 Chrysler New Yorker
The 1969-1973 Chrysler New Yorker is a behemoth of a car – it could be alongside the Lincoln Continental MkIV as the definition of ‘land yacht’. The car is 224 inches long, 10 inches longer than a modern Mercedes S-Class LWB. The engine is a big, lazy 7.2-liter V8, producing 220 hp and 460 lb-ft of torque, mated to a 3-speed automatic gearbox.
The New Yorker is the perfect car for cruising about or doing scenic road trips on weekends. Just be sure to take along your wallet as the engine empties the 23-gallon tank in an average of 200 miles. These small inconveniences do not matter, as the 1971 New Yorker has a used price of around $15,000, making it one of the coolest Chryslers to exist.
4 2005-2010 Chrysler 300C
The Chrysler 300C is one of the most noticeable cars for sale in the last two decades. It was a relatively cheap, large sedan – with an optional V8 – which was (and is still) often mistaken for a Bentley or Rolls-Royce. The 300C does not have either of those luxury cars’ build quality, but it instead has an identity entirely of its own.
The 300C is still in production today, however, its days are numbered. The first generation featured a 250 hp 3.5-liter V6, but this could be upgraded to a 5.7-liter HEMI V8, producing 340 hp. The 300C also featured Chrysler’s Multi-Displacement System, meaning the car could deactivate half of the engine to improve fuel economy. The Chrysler 300C is available for under $10,000, with a good one going for about $6,000.
3 1965-1966 Chrysler Imperial Crown
In the 1960s, Chrysler established Imperial as its own separate make – much like Toyota and Nissan did with Lexus and Infiniti, respectively. Imperial would produce the more luxurious cars while Chrysler made the more affordable ones for the masses. This seemed to work well and as such, Imperial released several models under its luxurious umbrella.
One such car was the 1965-1966 Imperial Crown – a car instantly recognizable as the gadget-ridden car from Green Hornet. Not only is the Imperial Crown silver screen famous, but it is also gorgeous to look at as the design promotes a reserved elegance. It is one of the best classic Chryslers and many are available to purchase on the used car market for under $10,000. Beware, however, as some of them need major restorations to bring them back to their former glory.
2 2005-2006 Chrysler Crossfire SRT-6
The Chrysler Crossfire was an attempt at a small, sporty roadster to compete against the BMW Z4 and Mercedes-Benz SLK. Instead, it was a massive flop. The Crossfire was built during the time when Chrysler and Mercedes-Benz had merged to form DaimlerChrysler, so some platform and parts sharing occurred between the two.
For the Crossfire, however, it was a matter of copying and pasting the SLK’s drivetrain, making a different body, and slightly altering the interior. The Crossfire and SLK were even produced on the same assembly line! The most powerful version was the Crossfire SRT-6, which featured the same 3.2-liter supercharged V6 as the SLK32 AMG. The Crossfire was a bit of a hit-and-miss, but it remains a sought-after car – more so than the Mercedes on which it was based.
1 2012-2014 Chrysler 300C SRT
The second-generation 300C was a more grown-up version of the original car – a more elegantly sculpted body, a less in-your-face grille, and a more premium-looking interior. Under the hood though, it still had a large V6, a HEMI V8, and a new turbodiesel V6 borrowed from the Italians.
The stand-out version though, was the SRT. Gone was the 6.1-liter from the previous model’s SRT-8, replaced with a massive 6.4-liter naturally aspirated HEMI V8 producing 470 hp. It was fitted with a 5-speed automatic – a bit old-fashioned even for then – but the 300C SRT looked so much better than the equivalent Dodge Charger SRT. The 300C SRT is quite a sought-after car, with demand pushing the used value to well over the price of a brand new, entry-level Chevy Camaro. This does not matter though, as the 300C SRT is worth every penny.