Chrysler, the ninth oldest automobile manufacturer in the United States, conjures up divergent memories in the minds of car enthusiasts.

There are those old enough to recall the stately, high-end models of the 1950s, and conversely, there are people who grew up during the 1970s and ‘80s that remember the malaise years, when the company’s vehicles, such as the K-Car, were low-cost, prosaic machines.

Though the brand will enter 2024, the 99^th year of its existence, producing only two models of the same minivan, the Pacifica and the Pacifica Hybrid, there was, from 2005 to 2023, a sedan in its lineup that bore the name, and captured the essence, of a storied model far back in its past.

The car in question is the Chrysler 300.

The original 300 models, built from 1955 through 1965, were known as the “Letter Series” cars, as each year’s version bore a successive letter of the alphabet after the 300, beginning with the 300B in 1956. They were powerful, elegant, halo cars that were often the first vehicles to introduce new features and technologies to the industry.

In keeping with this tradition, after a forty-year gap, Chrysler reintroduced the 300, intending to carry on this legacy of cutting-edge performance.

In this installment of That Was Then, This Is Now, we will cover the entire history of this fabled car, to learn why it was such an iconic model in the middle part of the 20^th century, and again in the modern era.

Seeking to offer a true performance vehicle to its lineup, Chrysler introduced the full-sized 300 in 1955. Penned by Virgil Exner, future father of the Forward Look design program that incorporated airplane-inspired details, the 300 was one of the first American cars that featured long hood/short deck proportions.

Dubbed the “100-Million Dollar Look” by Chrysler’s ad department, the design also featured a lower roofline to what contemporary cars had, and was bequeathed smoother and more aggressive styling.

In addition to its groundbreaking exterior, the 300 packed serious hardware under the hood, consisting of a 331 cubic-inch “FirePower” Hemi V8. Outputting 300 horsepower (which gave the car its 300 moniker) the car also sported a free-flowing exhaust and a two-speed PowerFlite automatic transmission.

Despite all this goodness, the 1955 300 only saw 1,725 examples produced. But then, sales were not the point, having a halo performance car was.

The next year’s model, the 300B, had styling modifications to the tailfins making them more pronounced, but the biggest changes were afforded to the powertrain to keep the 300 at the top of the pyramid in terms of performance.

Two versions of Chrysler’s 354 cubic-inch Hemi V8 were offered, producing either 340 or 355 horsepower, the latter making the 300B the first American car to achieve one horsepower per cubic inch. With a then astonishing 140 mph top speed, the 300B achieved considerable success in NASCAR racing.

Sales were still lukewarm, however, dropping to a mere 1,102 units.

1957 saw a completely redesigned, second-generation 300C, featuring Virgil Exner’s aforementioned, Forward Look design. And what a car it was. With unique aesthetic elements including a large trapezoidal grille, a stepped V-shaped front bumper, quad lamps, a wraparound “Vista-Dome” windshield, and larger tailfins, the 300C was an iconic rolling design study in opulence, up there with contemporary Cadillacs.

The Hemi engine that powered the 300C was once again upgraded, this time to 392 cubic-inches (a size that will feature again later in this story) and a robust 375 horsepower.

Also new was Chrysler’s “Torsion-Aire” front suspension, Airtemp climate control system, and red, white, and blue, circular 300c medallions affixed to several locations on the exterior and interior.

The restyled car struck a chord with the public, as 1,918 coupes and 484 convertibles were sold, more than doubling the 300Bs totals. This, despite a soaring base price of $4929.

The 1958 300D was largely a carryover year for the model, but did see its 392 Hemi’s grunt increase to 380 horses, while an option called the Bendix “Electrojector” fuel injection system yielded a 400 horsepower output in a handful of cars equipped with it.

Likewise, the ’59 300E carried over for the most part in terms of looks, but had Chrysler’s brand new Wedge-Head 413 cubic-inch V8, which also put out 380 horses, replacing the 392.

Inside, luxury amenities were extended to include a comprehensive gauge package, and seats that swiveled when the doors were opened to aid in ingress and egress. Owing to an economic recession, the $5,319 hardtop and $5,749 convertible did not sell well, with only 522 and 125 leaving the factory respectively.

Just in time to offset these immensely poor sales, a third-generation was launched in 1960 in the form of the 300F.

Based on Chrysler’s new unibody construction, the F’s bodywork was decidedly sharper with more angles and cut lines, incorporated the corporate style grille present on all other Chrysler cars, and had tailfins that tilted outwards for a “Jet-Age” look. A Continental trunk with a faux wheel protruding from the lid completed the transformation.

Mechanicals consisted of an improved version of the 413 Wedge-Head with a “Cross-Ram” intake that improved breathing.

Innovations, which the 300 series was largely known for, included four bucket seats for front and rear passengers (with the fronts still featuring swivel functionality), an AstraDome instrument cluster with “Panelescent,” electroluminescent illumination, and push-button controls for the TorqueFlite automatic.

Sales took a modest jump to 969 hardtops and 248 ragtops.

For ’61, a restyle was performed on the G model, with the grille shape changed and the quad headlights stacked diagonally atop one another in a bold statement. Lesser change was also on the agenda for the next year’s H model which saw the total elimination of tailfins.

The fourth-generation car came in the form of the 1963 300J (“I” was skipped to avoid confusion with the number “1”). More mainstream styling was incorporated, with even crisper lines than the outgoing model, but the changes left many feeling that the opulence that the 300 was known for had been designed out. Headlights were once again quad, side-by-side units, the grille was thinned and stretched, and a wide C-pillar became a new hallmark.

Inside, the swivel chairs were eliminated, and amenities generally took a step down. Mechanically, the 300J stuck with the tried-and-true 413, now possessing an extra ten horsepower.

The public did not like what it saw, and despite Chrysler offering an industry-first five-year/50,000-mile warranty with the car, sales plummeted to an abysmal 400 units.

The 1964 300K introduced a restyled grille and taillights, and a console-mounted pushbutton transmission selector, while the exterior colors, which had always been limited to just a few options, was broadened to include 17 hues.

The price of the car was reduced considerably, with the hardtop starting at $4,228 and the convertible at $4,694. As a result, sales skyrocketed to 3,022 coupes and 625 convertibles, making the 1964 300K the most successful car in the Letter Series.

What was to become the final model in the 300 Letter Series run was the fifth-generation, 1965 300L. The first 300 not designed by Virgil Exner, but instead by his successor, Elwood Engel, the L departed mightily from tradition in its styling, incorporating the slab sides and tall greenhouse that had become omnipresent throughout the industry in America. Underhood, the 413 soldiered on, now downgraded to 360 horses.

A total of 2.405 hardtops and 440 convertibles were produced.

Plans for a 1966 300M were made, with subtle alterations to the looks of the L model and a 426 Hemi under the hood, but the project was cancelled, owing to the fact that the 300 Letter Series had lost their air of exclusivity and with it, their fan base.

The 300 nomenclature, was, however, briefly revived in 1970, when Chrysler teamed up with Hurst Performance to create the Chrysler 300 Hurst, a limited-edition, promotional model outfitted with a 440 cubic-inch V8. Most Chrysler historians agree though, that the car was not intended to be, nor should it be considered part of the 300 series. And with that, the Chrysler 300 name was resigned to history.

Ah, but history can be a funny thing…

In the late 1990s and early 2000s, a wave of retro-styled and retro-inspired cars had hit the market, capturing the imagination of car enthusiasts everywhere. The Ford Thunderbird, Mini Cooper, and Volkswagen Beetle had all been given the throwback treatment to much fanfare and strong sales, and retro Ford GT and Mustang models were in the works.

Chrysler, freshly merged with Daimler-Benz, took note of this trend and in 1999, attached the moniker, 300M, to a new LH platform sedan, picking up where the Letter Series had left off.

The car’s styling, V6 power, and front-wheel drive shared nothing with the famed models of the past though, and little connection to the Letter Series cars was established in the mind of the public. Sales were moderate, in the mid-30,000 units per year, and by 2004, DaimlerChrysler pulled the plug on all LH platform sedans in favor of a new architecture.

The LX was that new platform, and would incorporate many Mercedes components in its design.

In 2003, at the New York International Auto Show, Chrysler unveiled a concept car based on the LX platform, and called it the Chrysler 300. Unlike its most immediate predecessor, this 300 appeared to embrace Chrysler history not only in name, but in design and powertrain as well.

Styled by Ralph Gilles, the 300 concept was a retro, rear-wheel drive sedan that was intended to be a modern interpretation of the 300 Letter Series cars, and incorporated such throwback cues as the large grille, quad lamps, long hood/short deck proportions, and the low roofline.

Public reception of the vehicle was enthusiastic, and the production version, which didn’t differ much from the concept, entered production in 2004.

The car was initially made available in four trim levels, which included the base 300 equipped with a 2.7-liter twin-cam V6 outputting 190 horsepower, the 300 Touring and 300 Limited, each powered by a 250-horse, 3.5-liter single-cam V6, and the range-topping 300C, possessing a 5.7-liter Hemi V8 tuned to 340 ponies.

The V6s were mated to a Chrysler 42RLE four-speed automatic, while the Hemi transmitted its grunt through a Mercedes NAG1 five-speed automatic. The Touring, Limited, and 300C cars could be had in two-wheel or all-wheel drive versions.

Sharing its rear 5-link independent suspension with the Mercedes E-Class, and a double-wishbone front geometry derived from the Mercedes S-Class’, the 300 also borrowed its driveshaft, steering system, electrical architecture, engine modules, and HVAC systems from the Mercedes parts bin.

Exterior styling was a balance between the retro and modern, with the low roofline giving the 300 a chopped, gangster car appearance, while external touches such as the headlights, taillights, mirrors, and trim were assertively contemporary.

The interior was spacious, but featured rather cheap materials. Interior amenities naturally increased along with trim level, and included items such as real wood trim, leather seating, folding rear seats, power everything, and a selection of entertainment systems.

Perhaps the most important aspect borrowed from Germany though was the 300’s handling and performance. Though a large car at 197” long, 74” wide, and weighing in at a portly 4,273 pounds when Hemi and AWD equipped, the 300 rode solidly (many reviewers called it Mercedes-like) and handled well. What’s more, with the 5.7 on board, the 300C could hustle to 60 mph in a scant 5.3 seconds, and trip the quarter mile in 13.9 seconds at 102 mph.

Starting at just $23,405 for a base model, the 300C was like a godsend to the Mopar faithful for its contemporary spin on a beloved classic, and struck a chord with the general car buying public as well. First year sales were a resounding success with 144,048 cars produced, outselling all of the Legacy Series cars combined. Chrysler and Ralph Gilles had an unmitigated smash on their hands and would not rest on their laurels moving forward.

In 2006, Chrysler again shocked the market with a version of the 300 fine-tuned by Chrysler’s SRT (Street and Racing Technology) department, essentially Mopar’s version of Mercedes’ AMG or BMW’s M Division.

Called the Chrysler 300 SRT8, the car packed a powerhouse 6.1-liter version of the 5.7-liter Hemi that churned out a stout 425 horsepower, identical to the listed power of the classic 426 Hemi. Paired with an SRT-modified version of the NAG1 five-speed, the SRT8 was capable of a 4.6-second romp to 60, and a 13.1-second trip through the quarter mile at 109 mph. Impressive numbers for such a large, heavy car.

Other SRT touches included 20-inch wheels, Goodyear Eagle F1 Supercar tires, a specially tuned stability-control system, firmer suspension, large front and rear discs with four-piston calipers all around, and bespoke interior and exterior trim.

Priced at $45,450, the SRT8 sold like gangbusters to performance-minded 300 buyers.

In 2008, the 300 received a total interior update, with plusher materials all around, while in 2009 the 5.7 Hemi was reworked and its output raised to 360 horses.

But. it was 2011 that would see the most comprehensive changes to the 300 range.

The exterior was given a complete makeover, with sleek lines and more traditional contours replacing the gangster vehicle motif. Modern touches such as Bi-Xenon headlights, LED taillights, and a reshaped grille were just some of the new flourishes.

Inside, everything was reworked, with a push towards luxury materials and amenities that approached that of many domestic rivals. An 8.4-inch Uconnect touchscreen with available navigation was present, as was a new gauge cluster with blue illumination.

Mechanically, the big news was threefold. The anemic 2.7-liter and 3.5-liter V6s went the way of the Dodo, replaced by the Pentastar V6, an efficient motor good for 292 horsepower, while the 5.7 saw a modest boost to 363 ponies, and the 6.1 Hemi in the SRT8 was replaced by the thundering, 470 horse, 6.4-liter Hemi (392 in cubic-inches. Does that number sound familiar?)

From 2011 on, the 300 line was updated here and there, and included the replacement of the old 5-speed with a ZF-sourced 8-speed TorqueFlite, the addition of active dampers on high-end models, and a mild facelift.

Disappointment came for 300 gearheads in 2014 though, as the SRT8 model was discontinued (though it would live on in foreign markets such as the Middle East and Australia.)

Sales of the 300 eventually dwindled as the years passed, and in early 2022, Chris Feuell, CEO of the Chrysler brand, announced that 2023 would be the final model year for the venerable and successful 300 line. She cited its demise as part of the company’s plan under new owner Stellantis to lean into “transformative, sustainable mobility technology that will make the world cleaner, safer and more seamlessly connected.”

Noting the 300’s success, Feuell announced that its sendoff would be commemorated with a final edition to be called the 300C Last Call that would mate the 300 with the 6.4-liter Hemi V8 for one last hurrah.

2000 units of the 2023 300C Last Call were ultimately built for the US and 200 for Canada. The cars were offered by first-come, first-serve reservation, and sold out in a mere 12 hours.

Offering all the latest 300 series tech, plus the hot 6.4 Hemi tweaked to put out 485 horsepower and paired to the 8-speed TorqueFlite, the Last Call 300C was essentially a fully updated and modern SRT8. Available only in Bright White, Gloss Black and Velvet Red, equipment and amenities included an active exhaust system, an active dampening suspension, four-piston Brembo brakes with red calipers, a 3.09 limited slip differential, a bespoke interior, and a special blacked-out grille.

But perhaps the most fitting item on the 300C Last Call was a red, white, and blue “300C” medallion on the grille and decklid. It recalled those of the Letter Series cars, establishing the link between the modern version and its forbears, and moreover proving that you can’t keep a good car down.