I’ve been going through my car photo archives recently, and thought it might be fun to put together a series of posts on my most “Memorable Drives” from my time as a car magazine writer and beyond. I was just telling the story of this car the other day, so what better place to start? Besides, it was a really cool car – and the owner was all kinds of chill!

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It’s clear that I did something very, very bad in a previous life. I can think of no other explanation for the torrential downpours that dampened any chance I might have had at fully experiencing one of my outright dream cars – a 1958 300SL Roadster. The 300SL is arguably the definitive classic sports car for Mercedes enthusiasts; from its bold three-pointed star to the graceful curves to the throaty exhaust, this is the stuff that automotive fantasies are made of. But alas, it was not to be. Not for me, not this day.

When first approached about writing a piece about the 300SL Roadster, I was beside myself.  I’d been tasked with compiling any number of pieces about ordinary, esoteric cars but never something iconic. I immediately called my Car Geek buddies to gloat! I could just picture touring the scenic New England countryside on a warm, dry day. Top down and not a care in the world, the wind in my hair, and the sound of the race-bred engine for a soundtrack, I would doubtless file this under experiences of a lifetime. First, however, I needed a car. I contacted old friend Alex Dearborn in Massachusetts to solicit advice and direction. Surely Alex, with his expansive database, would know someone willing to let a hack automotive journalist have a crack at his car.

Alex referred me to Barclay Henderson, a dignitary with the Gull Wing Group, who just happened to have a car about to come out of restoration. Barclay was willing and able to help! His car, on the other hand, would be far less cooperative. With print deadlines rapidly approaching it became increasingly obvious that Barclay’s car would not be finished in time. Restorations, as many of us know all too well, seldom follow an exact timeline, and this one would be no exception. Barclay made a few calls on my behalf and shortly came back with what he described as a “yellow roadster with green interior – but it’s much better than it sounds.” And he was right, as evidenced by the pictures before you.

The other thing that will stand out glaringly in these pictures is the rain – the terrible, awful rain. See the glittering reflections of the headlights on the road? That’s just the beginning. All that rain, however, did little to quell my enthusiasm for this car. When photog friend Kaveh Sardari and I arrived, the car was ready and waiting for us to explore every inch.

From Greatness to… Greatness

A brief history lesson here: The 300SL started life as the renowned Gull Wing race car released for the 1952 season. It was named on the basis of displacement (3.0 liters) and type – in this case Sports Leicht, or SL. It was engineered, under the guidance of Mercedes test department head Rudolph Uhlenhaut, to be as light and powerful as possible.

Uhlenhaut’s efforts paid off in droves.  The 300SL excelled in European racing circuits and achieved its first win at Le Mans. From there, piloted by the likes of such greats as Rudy Caracciola, Karl Kling, Hermann Lang, and Helmut Niedermayr to name but a few, victories were achieved at the Nürburgring and Carrera Panamericana. The 300SL was clearly a force to be reckoned with.

Meanwhile, back in the US of A, wealthy entrepreneur and Mercedes-Benz importer Max Hoffman urged the boys back in Sindelfingen to produce a street version. Hoffman reasoned that the Mercedes line distinctly lacked models with a sporting image, and a production 300SL would fill that void perfectly. After serious consideration and (more importantly) a commitment from Hoffman to purchase the first 1000 cars, Mercedes ultimately decided to build a marketable 300SL.

The production 300SL was released at the 1954 New York International Motor Sports Show to rave reviews. It was the talk of the show circuit, and everyone who was anyone wanted one. It was also a veritable bargain among the more expensive 300 series coupés. 1,300 “Gull Wing” coupés were produced from 1954 until 1957 when production transitioned to a mildly redesigned roadster version.

Mercedes had planned a roadster version of the 300SL from the start. The Gull Wing, while a natural for road races and touring, had its downsides. For a start, ventilation in the coupés was abhorrent. On a sunny day, occupants would be roasted in a matter of minutes. It became regular practice for owners to raise the doors while waiting for traffic signals to change. The coupes also had what can best be described as “squirrelly” handling. The new roadsters addressed these issues, as well as paying adage to the common perception that only open cars can be true sports cars.

Minor modifications were made to provide for the new configuration. Obviously, roof-hinged doors would not work on a car without a roof, so the space frame was modified to utilize a more conventional door design. Additionally, fuel-tank capacity was reduced in order to increase storage space, and a low-pivot swing axle with coil springs was fitted to the rear. In 1961 four-wheel Dunlop disk brakes were fitted in place of the original Alfin drums.

Overall, these modifications, coupled with the added weight of chassis strengthening and convertible-specific hardware, resulted in a weight gain of approximately 200 pounds above the coupé. To counter the additional weight, the engine received a competition cam and a revised final drive – from 3.64:1 to 3.89:1.

Gull Wing fans and purists were less enchanted with the convertible version, but that didn’t affect sales. In fact, between 1957 and the end of production in 1963, Mercedes produced 458 more convertibles than coupés, for a total of 1,858. One of those cars is the one you see here – the one I was about to experience.

On the (drenched!) Road

In a move that surprised us all (including his wife, I’m afraid), Charles Rosak, the owner of our yellow roadster, agreed to take it out – top up, of course – in the pouring rain. “After all,” he said, “it’s just a car.” Yep. Conservatively a $275,000 (in 2003 dollars – about 5 times that in 2025, give or take!) car, but who was I to argue? I felt a little (a LOT) like Ferris Bueller climbing behind the wheel of Cameron’s dad’s Ferrari California Spider.

The 300SL Roadster fired to life with a growl, then like every other vintage Mercedes I’ve known, mildly stumbled through warm-up. It takes quite a while to warm eleven liters of motor oil.. As it warms, there is unique mixture of sights, sounds and smells: you see the car coming to life through condensation emitted from the tailpipe in perfectly timed fashion; you hear the car smoothing out as the temperature needle rises; and the smell – ahh, the smell that is part unburnt fuel and part rich leather – is a combination you have to smell to love, and you will love it when you smell it!

As agreed, the top went up before anything else. A short series of twists and turns secured the convertible top in place. Compared with its contemporaries, the 300SL’s mechanism is a marvel. I remember a friend with an old Healey – it was like wrestling an alligator to raise the top. Once there, it hardly made a difference. In contrast, this top went into the proper position with ease, and once secured seemed almost vault-like.

The car slid into gear with the ease of a much more modern car, and took up with aplomb – smooth as silk. This was clearly a car ahead of its time! At one point, it was as docile as the sedan from which its basic engine was borrowed, but in the flash of an eye and snick of the gears it rocketed away, still singing its merry tune. This car has dual personalities – part boulevard cruiser and part street racer – both equally satisfying in its own right.

Probably the most interesting part of the road experience, even in this dismal weather, was the reaction from passers-by. On four-lane roads, other drivers sped up, slowed down, changed lanes, and drove like maniacs just to catch a glance. It’s not every day that you see a 300SL Roadster, especially in a deluge! But this car has a presence: an almost regal aura that surrounds it as it wanders about the landscape, drawing the undivided attention of everyone in its presence.

Up Close and Personal

Close examination of the details throughout this car reveals a pride in craftsmanship that you just do not find in modern cars. Every part of the 300SL appears to have been designed with a specific set of instructions: “Make it functional and make it beautiful.” Period.

I wasn’t looking at the details, to be quite honest, until we started shooting pictures. Diligent photographer Kaveh was clicking away, but I couldn’t tell where he was aiming the camera (bear in mind – we were still shooting real, live film back then!). “Look at this,” he said excitedly, “this chrome is fantastic!” He was pointing to the chrome strip that rides the length of the door top and flows into the windshield. It looked as if it had been honed from a single piece of metal which then had a car built around it.

Upon closer examination, I found subtle and not-so-subtle details to admire from every angle. I was mesmerized by the air duct in the front wings, the heater control, the intricate convertible top mechanism, even the speaker grilles – it is all fantastic! I could spend hours admiring this car from every angle.  Standing in front of it, I admire the upright grille that became a trademark for the SL.  Sitting inside, the finery of the ventilation controls, the radio, and even the window crank is as pleasing to the eye as to the touch.

My favorite detail was the exterior door handle – aircraft-grade aluminum mounted flush against the door skin with only a slight tab protruding. A gentle push on that tab revealed a handle designed to fit a hand – my hand! I could wax poetic on these things for hours. As the old adage goes – they just don’t make ‘em like this anymore.

And the Beat goes On

I imagine driving my 300SL roadster through the warm, sunny palm trees and golf courses in Palm Springs, California.  If you’ve never been there, Palm Springs is an oasis in an otherwise barren space, but its unique charm has attracted the likes of Frank Sinatra, Bob Hope, and even (former U.S. Congressman) Sonny Bono.  It one of a small handful of places on earth where every day is a convertible day, and this is definitely one to have.

And who doesn’t want to be seen in a 300SL roadster? Better yet, who doesn’t want to drive one? With timeless styling and unmistakable personality, this car stands out as among the best cars of all time. It captured the essence of performance and luxury – a concept that modern manufacturers still wrestle to this day. 300SLs also retain an enthusiastic following, most notably the international Gull Wing Group – over 600 members dedicated to the admiration, care and maintenance of 300SL coupés and roadsters.

So despite the washout, who am I to complain? I spent a day in the presence of greatness, and I am grateful for it. The 300SL Roadster is an amazing automobile, and a work of art in its own right. If anyone out there wants to let me drive theirs for a sunny weekend, just drop me a line. I’m in the book.

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Special thanks to: Alex Dearborn, Barclay Henderson, Charles Rosak, and The Gull Wing Group (www.gullwinggroup.org)

Photos by Kaveh Sardari (www.sardari.com) except where noted