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Jul 26, 2022

Driven: The great American love story between classic cars and the men who drive them

Amy Bartlett

Photography By

2Lights, 1Stand Photography
Love drives us crazy. What draws us or makes our eyes light up and why is the great unanswerable question, whether that’s a person, a song, a place—or one particular car, made one year, in one perfect color. Muscle cars, luxury sports, collectable classics, flatbeds with four on the floor and dripping in pure Americana. […]

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Love drives us crazy. What draws us or makes our eyes light up and why is the great unanswerable question, whether that’s a person, a song, a place—or one particular car, made one year, in one perfect color. Muscle cars, luxury sports, collectable classics, flatbeds with four on the floor and dripping in pure Americana.

When it comes to cars—classic, collectable, vintage, vogue, fast, furious—unanswerable though the question may be about our longstanding love affair with the king of the road, six southern gentlemen give the answer a good go. Jim, Phil, Bill, Michael, Rob, and Mike grab the keys to take us back in time, through the garage, and cross the double yellow to head into the sunset with their favorite set of wheels.

Mike Iannazzo, his German Shepherd Fonzie and The Golden Boy, a ’55 Chevy Bel Air.

The starting line

Ask any man or woman who ever loved a car and they’re likely to take you back to their first. Not just a bygone era when cars were cool and crowned in chrome, but to a discovery of a driving passion.

Phil Sirmans wins a proverbial best in show for the memory of his first four-wheel love, with a story that couldn’t possibly get more “Wonder Years” if it tried. Already a young car enthusiast who says it was his dad who lit the fire for fine cars, Sirmans’ voice lifts when he tells of the one-dollar bill of sale that landed him his sweet-16 set of keys.

“I used to love to get the new Auto Trader at the gas station and scavenge through it. I had spent the summer cutting grass for this lady who was my dad’s second grade teacher. She said, ‘I know you’re turning 16. I have something in the garage you should have.’ I didn’t even know what kind of car was in that garage. She sold it to me for a dollar; we had it towed to our yard, and when I pushed it out and opened the hood, a giant rat fell out.” Sirmans paused here where you’d think this bucket of bolts story is going to buckle, but without missing a beat he said, “I had it running in a week.”

The car in the garage was a ’79 Plymouth Volare. Two-toned blue. It was love at first rat. But it would share a parking space with another gas-guzzling great when Sirmans’ dad asked for his car wish list. “I gave him an impossible option and a not so impossible possibility (I figured it was a good negotiating tool to force his hand a little), a late ’80s Lamborghini Countach or a black ’87 El Camino.” Another pause drives the drama with an impeccable timing belt before Sirmans added, “You can guess which one was sitting in the driveway.” 

Theirs was a story passed down from one generation to the next. It wasn’t the first—or the last—or the millionth; turns out “I got my love of cars from my dad” is a whole vibe. A genre. A longstanding tradition. But “Dad” levels out further to a whole range of influences between the guys (and gals) who just love cars, and that big wheel keeps on turning.

Art you can drive

Bill Head, owner of H & H Auto with his 1969 Z28 Camaro.  

There’s barely a father-son duo who radiates this more than Michael and Bill Head, known for their mini-fleet of personal classics and for H&H Auto on the island, the go-to for so many lovers of luxury and well-made machinery. Michael Head words it nearly as beautifully as the sleek and timeless line of the Mercedes style they both love: 

“My love for cars started with my father who has dedicated most of his life to restoring and preserving Mercedes Benz and other classic cars. I realized at a very young age that he was not like other dads who collected baseball cards or other knick-knacks. He collected art you could drive. It’s art that moves you—personally, emotionally, literally. It moves you down the road, at the mph of your personal choosing. 

Michael Head sits in a 1966 230SL Mercedes Benz.

When Bob Head talks of cars, you hear where Michael Head gets it. Head Sr. speaks of cars matter-of-factly, as if their greatness is a given. He talks of them humbly, referring to his early acquisitions as pace cars that set him on the right track. “Fifty-five Chevy,” he said quietly, and “1970 Chevrolet Chevelle,” with the gravity of memory, like a favorite piece he recalls hanging in a gallery. His appreciation is pure; when asked what he loves about the world of classics, where many talk of driving, showing, building, Head said with respect and genuflection, “I just love the car itself.” If that doesn’t cut straight to the heart of any aficionado, I don’t know what does.

Asked when he began to take cars seriously, he said with the sound of drawing a line in the sand, “I have always taken it seriously.” He took his passion (“hobby” wouldn’t do it justice) and turned it into a business, a career, a lifestyle, and nowadays, a small catalog of cars. Above all, he speaks of cars as you speak of industrial arts: the machinery, engineering, maintenance, manufacturing, the automotive science behind building the rocket itself. He takes pride in the work of the business he’s built. “It’s rewarding to see the quality in the make of the vehicle and to be a part of that—to leave it better than you found it.”

A few stars in Bill Head’s fleet (rom left to right): 1966 230SL Mercedes Benz, 1971 280SL Mercedes Benz, 1961 190SL Mercedes Benz, and the 1969 Z28 Camaro

 Leaving it better than you found it, and the value of a multi-generational influence, is something Mike Iannazzo and his current business partner (and former high school auto tech teacher) Rob Iulo know from experience. Iulo similarly learned the tricks of the trade school when he was a teen from buddy Rich Conklin, with whom he started Radir Wheels which specialized in what they called “new-stalgia,” offering American-made, vintage-designed wheels. Fast forward, the student became the master and started Land Speed Automotive with his former teacher. And the cars that drove them wild? All three had a thing for ’55 Chevys, but then there’s the 1932 Ford Deuce Coupe that keeps crowds singing “Little Deuce Coupe” in their soul every time they catch a glimpse of Iulo’s pride and joy.

Cars are stories

Jim Russell with his 1967 Chevrolet Corvette

Like so many of his automotive fellows, Jim Russell fully appreciates how meaningful memories can be both to the driver doing the reminiscing and to the listener. “Cars are stories,” Russell said, touching on one of the strongest elements in our sentimentality for steering wheels.  For Russell, it must be mentioned, this meant a ’63 split-window coupe corvette only made for one year. It was the only one with split window, and it took him back in time.

It’s a sentiment repeated by his peers. Mike Iannazzo said, “It’s about remembering the way things were. It slows life down and makes you think of a different time.” 

“Being around and driving a classic car, to me, is the closest thing to time travel, going back in time and seeing how simple things were,” Michael Head said.

By different time, Iannazzo hits on a subject larger than lingering memories. “Cars today have spoiled everybody,” he said about the creatures of comfort we are and our climate-controlled cocoons with surround sound, four-color GPS, OnStar, push-to-start, seat setting memories, and parking assist. God forbid the self-driving cars known as autonomous vehicle (AV). It’s inhuman—literally removing the drive from the driving equation in every sense.

“But when you’re riding in an old car,” Iannazzo said changing his tone,” you’re reminded, people were made of steel! We were driving around for miles in the heat and cold just to go on vacation. No conveniences, just power. The car has evolved amazingly. But we’re soft. We’re not building our cars in our garages and taking them out on the open road to find what we can find, with or without air conditioning.”

A paper plate 10

Not only does the contemporary ease of comfy cars call into question our collective “steel” and “mettle” (all puns intended), but it troubles the waters of another human condition: the need for connection.

“I love that classic cars bring people together from all different backgrounds; everyone is always excited to share with you who/when/where/how they acquired their classic,” Michael Head said.

Jim Russell put this shared love at the top of the list like the others. “I like to drive, hitting the throttle and the feeling of driving, but when you have one of those conversations where people recognize what they love—‘Is that a ’71? I used to have one of those!—that’s the most fun, driving and seeing people’s expressions when they remember too.”

“My love for old cars has always been the drive, but, it’s also seeing people build their own cars, bringing something like that to life, and sharing what they’ve built with others,” Mike Iannazzo said. “Like my ’55 Chevy Bel Air—the Golden Boy. It’s completely impractical. My car’s kind of wild and gets the attention of people who like cartoony cars. It takes the imagination somewhere else. Especially when you get a kid giving it a big thumbs up or a paper plate with a number on it. When you get a kid with a paper plate 10, it doesn’t get better than that.”

Sirmans recalls an equivalent tucked in his window during an event. “I love car shows but never entered one. I just like going to them. One year I was working the Concours d’Elegance, and a guy left his business card on my truck where I was parked in the employee parking lot asking why the truck wasn’t in the show. I never contacted him, but what he got out of it, I still get out of it. Sometimes I just like to sit in the garage and look at it, but it’s so much better when you see someone else appreciate something like this and you get a big thumbs up or a honk—any little gesture that tells you they see it too.”

Rob Iulo with his 1949 Studebaker. Iulo owns Land Speed Auto.  

The cars we love

They only have the chance to “see it” because there was a driver who saw it first—who sometimes saw the diamond in the abandoned and rusted-up rough and got it running. Made it something to behold. Art you can Drive. The cars we love.

Sirmans said, “I love a lot of things. I like to cruise, and to build, not from the ground up but restore. But sometimes I literally get out of the car, turn around and give it another look.”

That’s something we’re all pretty guilty of. Counting by the classic car shows around the nation, including annually right here on HHI, or weekend pop ups from Parris Island to Sea Pines, there are more than a few of us turning around to simply give the gorgeousness one more loving look.

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