The Chrysler 300 has basically been with us since 2005, and it last got an update in 2011. That makes it the car equivalent of half the lineup of the San Antonio Spurs. But people still seem to want them! People like my friend Rich, who I’m writing this review for. Look Rich, and other Richs of the world, here’s what you’re getting yourself into.

(Full Disclosure: Our Reviews Editor Andrew Collins begged FCA for some wheels to run around in during the Detroit Auto Show, so this all-wheel drive 300S was delivered to us at the Wayne County Airport with a full tank of gas.)

Dear Rich,

If you asked me to describe the cliché Chrysler 300 driver a few things come to mind: Middle-agedness. Middle-managementness. The fact that no hip young person will ever see this car and say “I bet that gets great gas mileage” or “does it let me Snapchat while driving?” They want muscle, or at least the perception of it, and refinement, or the perception of that too. The car is classically stately looking, which will translate to bland stuffiness or timelessness depending on who you ask.

When your fiancee told me that you wanted to buy a Chrysler 300 I politely nodded and said what any good friend would say to you about this purchase: “Why the fuck do you want to buy a 300?”

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You said to me, in your gingerly way: “Because I’m an old man and I want an old man’s car!” Well, I can’t fault you for that, this is certainly the car for an old man. But can a 30-something get away with buying this car and enjoying it?

Since your other choice was a Dodge Charger, I don’t even know, man. That’s just angrier-looking side of the same coin. Er, I mean car.

But now that I’ve had the chance to drive this thing, I can actually shed a little more light on what it was really like to live with. For you, Rich. The other two cars we had at the Detroit Auto Show were a Jaguar F-Pace and a freaking Mercedes-Benz S-Class Coupe.

Have you ever sat inside an S-Class Coupe? It’s like the comfort-spawn of dad’s favorite office chair and a hot tub. And here I was slumming it in the $38,000-optioned-to-$49,000 Chrysler just so I could tell you about it driving it. You’re welcome.

And drive it I did. On Detroit’s many terrible roadways, on Detroit’s few good roadways, at night, in the snow. We got a whole lot of different experiences in the Motor City: it has everything from straight roads to intersections and pretty much nothing between. In a few days of criss-crossing the city’s grid, we put close to 200 miles on the thing.

Our fancy alligator-green 300S AWD was powered by a Pentastar V6 engine pushing a claimed 300 horsepower and 260 lb-ft of torque to all four wheels through an eight-speed automatic. This was not the mighty 300C, with a 363 horsepower 5.7-liter Hemi V8. And unlike its Dodge cousins, the Chrysler—one of just two cars left in the modern Chrysler lineup—does not get obscene, ludicrously overpowered versions with vulgar names like Hellcat, Scat Pack and Demon. It has the same blood, but it puts on a suit every day and goes to work, leaving regular brawls in hockey game parking lots to the family members who have more interest in that sort of thing.

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Navigation, an apparently upgraded speaker system, whatever the “S Model Apperance Package” is (color-matched body bits, accent lights, black grille, LEDs -Ed.) and a few other pieces of modernization that make the 300 into a car really worth considering pushed the MSRP to an eyebrow-raising $49,660.

If nearly 50 grand for an upfitted seven-year-old Chrysler seems like a supremely poor way to spend your money, congratulations, you’re not a complete lunatic. That said, Jalopnik’s car buying expert Tom McParland restored my confidence in capitalism by telling me that dealer incentives make the actual price on these significantly more palatable.

Speaking of, the Chrysler 300’s main value proposition in 2018 is still not radically much different from the one that came out in 2005: If you’re standing 20 feet from it at night time with no moon out and squint a little, you might almost kind of mistake it for a Bentley.

Our tester came in a deeply perplexing color combo: metallic Army camo green with bronze wheels. None of us had ever seen such a car out on the roads, not this far from SEMA anyway. I’m not sure if it fell asleep on a Jeep production line and ended up this way or if the person optioning the car out was just blind, but it didn’t do the car’s looks many favors. And I hate the front grille anyway, it looks more “Canyonero” than the old money class I think Chrysler was going for.

My experience improved when my colleague Raymond Cinemato and I actually got the 300 started, though. Detroit was 15 degrees when we climbed into the car, the misery of which was quickly allayed when I realized not only were the car’s seats heated, but its steering wheel was too. Hell yeah, that $1,895 300S Premium Group 2 options package was starting to feel pretty sweet indeed.

Those heated seats are comfy, too. And the instrument cluster’s pretty easy to navigate.

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Now you remember the ’89 Eldorado I had in high school that we almost wrecked the first week I got my license, so obviously, I know a thing or two about American luxury cars. And as soon as I started mustering the 300 out of its parking space I remembered what it was like to wield a large sedan.

Let me simply say that the Chrysler 300 seems to have the effective turning radius of a very large shipping vessel. Much like the vessel you are Chief Mate on, Rich, so this is a plus for you!

You can leave your job cruising the Gulf, come back, and feel right back at home on the bridge as you carefully nudge and steer your 300 around potholes.

There are more potholes in Detroit than anywhere else I’ve been in America. Trying to avoid them is like trying to avoid pedestrians in GTA V- even if you want to, eventually it’s like... screw it. Brace for impact. The skinny sidewalls of the 300’s tires don’t love to bash through these bumps, but the car’s compliant enough to generally keep coffee from coming out of the cupholders in regular rough-city driving.

Once you do escape bombed-out surface roads, the 300 provides a perfectly comfortable highway cruising experience. The V6 is healthy too, and has no problem propelling the car to antisocial speeds should the occasion call for it. It’s no Hemi, but it gets the job done better than most people would expect. While that’s happening, the cabin remains remarkably quiet.

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I didn’t always drive, either. Raymond took the wheel at times and gave me the chance to sit in the passenger seat. This, perhaps, is the seat from which to best appreciate the 300. The touchscreen and other toys in the center console are easy to navigate from the right seat, and the back even gets seat warmers if you splurge for them.

The trunk swallowed all our camera gear, meaning your luggage will disappear in there easily.

So Rich, I’m not sure what else to tell you about this car. Really, the Chrysler 300 is exactly what you and probably most people reading this think it is: an OK execution of old-school Americana on wheels. The platform it’s on is so old that it’s all paid for, and basically just prints pure profit for Chrysler whenever someone buys it. And despite its age, it still drives well and has some great luxury options.

You love comfort, you love boating, you drove a Chevy Malibu for 12 years and in other words, you’ve always been an old man trapped in a young man’s body. But your biggest hurdle will be convincing your fiancee to go for it. She actually has style, and this is not a stylish car—at least, not in the colors we had.

But stick to your guns! Know that I will gladly ride around the Bronx River Parkway with you in this bad boy. In fact, I’ll probably sit in the back with the seat heater on. Just please pick a different color than metallic green.

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Yours truly,

Adam