“You can’t know where you’re going until you know where you’ve been” is the kind of lame, sing-song fortune cookie saying you get from time to time in lieu of an actual fortune. And while on most days, I think it’s merely a hokey way of reminding people that the past is important, when it involves two very special Mercedes-Benz convertibles 60 years apart in age, it has its place.

The extraordinarily nice thing about the car community is most everyone’s willingness to share. We might have different tastes and come from all walks of life, but we’re always happy to chat cars and check out what other people’ve got.

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One day, at the end of last August, I received an email from Todd Jenkins in Richmond, Virginia, who wrote in to say that he had a 1957 Mercedes-Benz 300SL Roadster that he was willing to have me come drive.

You don’t turn down an email like that.

So, we picked some dates to go down and meet the car—but why stop there? I reached out to Mercedes, describing the situation and asking what they had in the fleet to match. They responded by setting me up with a 2018 Mercedes-AMG GT C Roadster for the weekend.

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It was an incredibly rare opportunity to see how Mercedes’ current halo convertible flagship really compares to its ancestor from the 1950s and how far luxury and performance and all the things Mercedes is supposed to be known for has evolved over six decades. Who could say no to that?

(Full disclosure: Mercedes-Benz wanted us to drive the 2018 Mercedes-AMG GT C Roadster so badly that it dropped one off at the office with a full tank of gas.)

A Sword For Today

The GT C Roadster is the sharpened-up version of the “standard” GT Roadster (I use the most sarcastic of air quotes I can muster here). Its 4.0-liter twin-turbocharged V8 now produces 550 horsepower and 502 lb-ft of torque. Power is delegated via a seven-speed dual-clutch transmission, sent to the rear wheels.

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And there’s rear-wheel steering, too, with up to a 1.5-degree toe angle. While that might not sound like much, it makes a difference in the driving (more on that in a bit)—and you can see it in action as well. Cut the steering wheel all the the way in one direction and you’ll see the back wheels do a little squiggle as they point against the direction of the turn at low speeds to tighten the turning radius. At the higher speeds (above 62 mph), they’ll turn in the direction of the corner.

You’ll need that extra help around tight corners, too, because the GT C Roadster is a wide car, bumped out by 2.7 inches from the normal GT Roadster. Street parking it (momentarily, not for, like, hours) in Manhattan is harrowing: bicyclists brush by—close and bold—but they can’t help it. The car just takes up that much horizontal space. Massive, 305-section tires wrap the rear wheels, giving it a very planted, hunkered-down look.

As does its front. The grille is vast and gaping; the three-point star on its nose, where all the radars for the fancy cruise control live, is bigger than my hand. The hood is looooooong. Head-on, the car gives off low-slung, prowling airs. From the side, though, the hood reaches far out into the horizon, parting the waves of traffic and granting you passage. It’s dramatic, about as subtle as a great white shark, and draws stares and gasps from nearly everyone who sees it. It is a striking machine.

Climb in the driver’s seat and it’s like settling into the cockpit of a jet. The carbon fiber accents were tastefully done and numerous taps and knocks to different surfaces yielded solid-sounding responses. Our test car, with a black and “Red Pepper”-wrapped leather interior, made it feel especially like sitting in a furnace. It’s not a criticism.

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Despite how large the car is on the outside, its size doesn’t translate to much space for the humans sitting inside. The center console, with its military sci-fi array of buttons and dials, is wide, imposing and takes up far too much valuable space. There are two cupholders, though.

And the GT C is hard to see out of, even with the top down. The belt line is so high, the nose sticks out so far and you’re sitting so low down that driving it around town is a game of approximating where it ends at all times. All those sensors really come in quite handy.

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Across Manhattan’s pockmarked and generally wretched roads, the ride wasn’t terribly pleasant. Unsurprisingly, the GT C rides hard, but its suspension isn’t the usual suspect. That system makes the car feel solidly wrought from a single piece. You always know what’s going on beneath all four wheels. No, it’s the infernal AMG sport seats, which are akin to sitting on wood. Wonderfully bolstered and laterally supportive wood, with awesome heating and cooling abilities, but wood all the same.

This made me apprehensive about the 350-mile ride down the Richmond, but I sucked it up because driving a GT C Roadster was well worth it. Top down the whole way, you ask? But of course. The car is marvelous at maintaining a stable internal temperature despite the top and windows being down.

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And weirdly, by the end of the drive, I had accepted the ride quality and the seats. I had altered my standards of comfort to fit the car. Is that weird? Honestly, it’s because everything else is so staggeringly good that you simply don’t care about stupid things like comfort anymore.

Switch the car into Sport Plus or Race Mode and suddenly, you’ve got an exceptionally balanced sword in your hands.

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Power delivery is every bit as sharp and deadly. The blown AMG V8's guttural yell never reaches the sonic peak that the old 6.2-liter naturally aspirated engine did, but what is missing in theater is made up for in pure, heart-stopping acceleration. The kind of acceleration that leaves your guts behind, shooting you into eye-watering warp speeds before you remember to breathe. There is no discernible turbo lag.

Steering: delightful and hydraulic. One of the last such cars you can buy today. The result is a crisp and sharp turn-in, aided by the rear-wheel steering that make even short jaunts around a parking lot an experience. In spite of its girth, the car is terrifically light-footed, pivoting around turns like a dancer. That, paired with the lightning-quick and snappy shifts of the DCT, makes it an utterly complete package.

I’d never driven a car that felt so unshakably capable. Even the thuds that sounded from closing its doors inspired confidence. The sheer strength of the engine, the force of its brakes and its tight suspension all shouted in my ear that there was little this car couldn’t do. This was what modern was supposed to be. This was what modern was supposed to feel like.

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Friends have criticized the GTs for being “sterile,” and while I can certainly see why they’d say that, I also don’t think that sheer capability and absence of mechanical flaws should be confused with lack of personality.

I’ll give you an example. The last model-year 2018 car that I’d driven was the Maserati GranTurismo MC. It was a fantastic machine and certainly had “personality” in the way of charismatic engine notes and small squeaks and clangs here and there. But those were build-quality issues. It’s an old car. No amount of sensors and a backup camera can disguise that.

The GT C is fresh and new for Right Now—and it feels exactly that. It makes you wonder if Mercedes-Benz was making its cars as good as this in 1957, exactly 60 years before the AMG GT C Roadster. What was the pinnacle of 1957 automotive innovation like? That’s what I headed to Richmond to find out.

When Old School Doesn’t Feel Old

Jenkins’ 1957 Mercedes-Benz 300SL Roadster has been in his family longer that he has: his father purchased the car new from the factory in Germany on July 21, 1957, a few years before Jenkins was born. He believes it to be the first customer car ordered outside the home market and the 27th production model built. His boyhood memories with it are what make the car truly special.

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Over the years, this SL has had the normal consumables replaced, like the tires, filters, hoses and brake pads. Additionally, Jenkins had the interior leather and carpets re-upholstered, the soft top changed from gray to blue, gave the car two resprays (one in the ‘60s and another in 1996, but kept its light metallic blue hue), re-chromed only a few pieces of the brightwork and replaced the shocks and springs in 1996. In 2000, he overhauled the engine, replaced the pistons and valves and detailed the whole thing.

The drivetrain is all original and has never been apart except for normal service. The suspension and steering components are also all original. He has the original tools, manuals, keys and spares that came with the car. One with a greater penchant for vintage cars than me would call it a numbers-matching example.

Jenkins delighted in pointing out small details of the SL after we parked in a quiet spot next to the James River. Tall and lanky, with a shock of silver hair, you’d almost think he’d have trouble fitting into the petite roadster. With an excited smile lighting his features, he showed me the discreet ashtray and cigarette lighter folded neatly into the passenger-side dashboard—a throwback to when smoking was a classy and movie star-like thing to do.

The turn signal wasn’t located on a stalk like on modern cars, you activated it by ticking a metal wheel mounted inside the diameter of the steering wheel left or right and then cancelling it again once you made your turn. And since the SL was designed to cruise on the Autobahn, the high beam switch was the same as the horn switch. One pull turned on the brights, a second honked the horn. The console’s polished metal recalled the decor of a classic mid-century diner. The thin shifter and handbrake pointed elegantly skyward.

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Getting into the SL involved climbing over its formidable sills—wide, because of the Gullwing’s design, which came first. And because this was a car from the 1950s, there was nothing in the way of seat belts roll-over protection. That, at least, made the visibility incredible.

Jenkins helped me scoot the seat as far up as it would go and it was my turn to drive. I never found out how much his SL was worth, but this 1960 model that sold for nearly $1.4 million gave me a good enough idea. It didn’t matter anyway: selling it would be like selling off a member of his family. I was honored to be allowed to drive it. Jenkins’ own children had never even driven it.

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Engaging high off the floor, the clutch was peppy and energetic. The Bakelite shifter and wheel felt too thin to be doing the job they was supposed to. But I pushed the shifter forwards anyways, where it slotted into the housing with a decisive clunk of metal-on-metal. The resistance made me feel like I was actually doing something, unlike modern shift action, where it’s totally effortless.

Jenkins advised that shifts didn’t need to happen until 4,000 RPM, so I let the engine sing up until then and threw it into second and made an involuntary noise of admiration. The action was notchy but smooth, riding along its mechanically carved-out path. I barely needed to give it any gas as I let out the well-weighted clutch to keep the speed up.

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The SL had ample torque and horsepower—in a letter from the factory to Jenkins Senior, Mercedes-Benz claimed 250 HP—making the sweeping Virginian backroads shrink easily to its capabilities. It glided over bumps and cracks in the road’s surface. It darted around corners and mail trucks with ease because of its sheer tininess. If you closed your eyes, you’d think you were riding in a present-day Miata. It just felt that modern.

That was the spookiest thing about the 300SL Roadster. It didn’t feel old at all. It was comfortable and agreeable. Totally daily drivable. I’m not sure what I was expecting, but I certainly wasn’t expecting something that felt comparable in quality to a car you could buy new today.

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Of course, braking and steering yanked me right back through the decades. The drums needed a lot of pressure through the pedal to bring the glorious body to a stop. Turning the wheels from a standstill was a full upper-body workout, as the steering was unassisted. I must have looked like an ass to some of the golfers standing idly by as we pulled into a country club parking lot to turn around, pipsqueak arms and legs straining to operate the wheel and the brakes.

But get it up to speed... you feel like a movie star. The wind through your hair. The raspy howls of the 3.0-liter slant-six engine. The low belt line. Regular SUVs to soar past. You feel like Natalie Wood. She also had a 300SL Roadster. It was pink.

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Of course, Jenkins has taken impeccable care of the SL, keeping it maintained and well looked-after. He does all the detailing work himself. But I think there is also something to be said about how well the car was made in the first place.

The Roadster followed on the heels of the instantly iconic 300SL Gullwing, which was the first production car to have direct fuel injection. But because the Roadster would obviously ditch the fixed roof, engineers gave it a reinforced and modified space-frame chassis. Designers streamlined its looks over the Gullwings by giving it a smaller grille. Obviously, the Roadster was easier to get in and out of than the Gullwings, which gave you something close to the size of an airplane window to climb through.

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The Roadsters had slightly smaller gas tanks than the Gullwings because the position of the spare tire was lowered so people could fit more luggage in its trunk. You can’t look at something like that and not imagine a glamorous road trip through the Swiss Alps.

Jenkins’ father paid 32,500 Deutsche Marks for the SL in 1957. According to this conversation table, that comes out to approximately $7,740. Adjusted for inflation, that brings us to just about $68,000 in today’s money.

The Family Resemblance

Undeniably, the 300SL and the GT C were nothing alike in how they drove. I didn’t expect them to be. The GT C has onboard computers and technology that people in the 1950s could only dream of ever existing. It can reach speeds that weren’t possible for most road cars 60 years ago with ease. And its advanced adaptive cruise control system means that you can travel in reasonable highway traffic without touching the brake or gas even once.

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Minus a few points for seat discomfort, it is among the very best that 2017 has to offer.

This is the thread that extends through six decades and ties the two cars together. Masterfully engineered, the 300SL was the height of automotive innovation and manufacturing in its day. Would the GT C Roadster exist today had the 300SL Roadster never been made? Maybe. It is Mercedes, after all. It will make quality shit long after we’re all dead.

But I think driving these two back-to-back speaks to the greater idea that while electronics in cars have evolved over the decades, the hardware of driving itself really hasn’t. All the controls in the SL were where they were supposed to be. I, as A Youth, had no issue getting behind its large wheel and putting it effortlessly on the road.

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Sixty years is a sizable passage of time no matter which way you look at it, especially through the lens of automotive development. It’s hard to say how cars will evolve from here in that amount of time, but I’m willing to bet that with the way things are pivoting to electrification and autonomy now, another comparison such as this one won’t be so easily had. The jump between 2018 and 2078 will be far greater and more dramatic than the one between 1957 and now.

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This makes me wonder: What similarities will the GT C have with a car 60 years from now? What similarities will it have with the 300SL, if any?