Haven’t I seen you somewhere before? It’s been 18 years since Chrysler launched their new 300C sedan. Since then, there have been various attempts at modernizing this boxy Millennial design, but despite generally wearing well, it’s showing its age compared to rakish rivals. A Bentley-aping grille and bulbous hood still give a good rear-view mirror, even if the overall appearance is of a bygone age; its side profile is particularly dated nowadays.

There’s a more contemporary ambiance once you open those heavy doors, though some of the switchgear still feels like it originated in the early Noughties – and with good reason. Prices have certainly moved with the times; a base model will set you back $33,000, while flagship S models will be nudging $50,000.

An old-fashioned approach to power. While modern rivals eke out every drop of power from increasingly compact engines, the 300 remains resolutely old-school. The 3.6-liter V6 is no shrinking violet, but the 5.7-liter V8 is a different beast entirely. Feeding 363 hp to the rear wheels through an automatic transmission is a recipe that hasn’t changed for decades. It also means disappointing gas mileage, though few people would spend almost $50,000 on a sedan that can hit 60 in less than six seconds and then fret about fuel economy.

Like American sedans of old, the 300 is extremely softly-sprung – some might say wallowy on base models with smaller wheels and tires. It does avoid the crashing or jostling associated with cars designed with one eye on Nürburgring lap times, making the big Chrysler a soothing companion on long drives. It’s not a car that encourages you to drive quickly, but the handling is decent considering how much weight needs to be shifted in the bends.

An equally old-fashioned approach to safety. The 300C’s manufacturing started before Facebook was launched, which gives you an indication of how long this venerable sedan has been around. While its design and performance have aged fairly well, it’s a long way off the pace in terms of safety. Consider the lack of standard crash-avoidance technology, the underwhelming four-star NHTSA rating, and the presence of words like “poor” and “marginal” in IIHS test results.

If you want to maximize safety, you’ll have to raid the options list for things like automatic emergency braking, while base Touring models can’t be specified with adaptive cruise or active lane control even as options. That’s not really good enough here in 2022.

Traveling in comfort. Chrysler has proved more adept at modernizing the 300’s interior, and the front seats are a lovely place to sit. There’s good visibility, plenty of seat support with power adjustment for the driver, and an 8.4-inch touchscreen with smartphone mirroring. Rear passengers won’t be as enamored, since there’s a distinct lack of knee room back here, but an impressive 16.3 cu ft of trunk space lies behind them.

As is often the case, higher trims tempt you with electronic goodies. Ventilated Nappa leather seats, real wood trim, and a 506-watt audio system greet buyers of flagship S models, though mid-range Touring L represents a good compromise with its sunroof, navigation, and heated rear seats.

Final thoughts. The 300 is an easy car to reach judgment on. If you want a comfortable freeway cruiser with a well-appointed cabin, plenty of power in reserve, and looks that can intimidate other vehicles out of your way, it’s got you covered. The V8 engine has vast reserves of power, the seats are comfortable, and a 500-watt stereo makes a symphony out of anything from disco to djent metal.

However, the 300 is showing its age in many respects, especially safety. It’s hard to overlook its disappointing official ratings, while the lack of standard safety technology is damning in an age when rivals can pilot themselves on the freeway and automatically stop for pedestrians. The 300’s looks are also starting to age, and it’s impossible to escape the sense that you’re driving a relic rather than a modern vehicle.

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Pictured: 2021 Chrysler 300