Friendly Competition and Banter are Tradition at Madison’s Two Barbershops

Frank Proto cuts customer Kevin Cassidy’s hair at Head Start Haircutters in Madison (CT Examiner).


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MADISON – Traditional barbershops have been gradually fading from the landscapes of small towns over the years, as salons become more prevalent. Nevertheless, Madison boasts two enduring barbershops, where the combined expertise of their owners spans nearly a century.

At 679 Boston Post Road stands Head Start Haircutters, run by Frank Proto, who has worked at the business for 43 years. Directly across the street at 708 Boston Post Road is Tony’s Barber Shop, overseen by Rich Santanelli, who has been at the same shop for 56 years, taking it over from the previous owner Tony Cavallero in June 2022.

“I’ve known him as long as I’ve been here,” Proto said of Santanelli, adding that they worked for the same boss at one point. 

Although the two establishments are technically competitors, Proto and Santanelli are friends and even cut each other’s hair. Their service prices closely align as well, charging $26 for a standard haircut and a discounted rate of $24 for seniors and children. The only notable difference is that Santanelli offers straight-razor shaves, while Proto does not. 

“We’ve always gotten along,” Proto said. “We both have very strong clienteles. If I can’t take somebody, I’ll send him there and he’ll do the same with me.”

Santanelli, 78, said Proto has even offered to share a workspace. 

“He would like me to come over there,” Santanelli said. “He says if you don’t want to work as much as you are, come over and work as much as you want. We’ll share some of the expenses.”

Santanelli said he hasn’t taken Proto up on the offer yet, as he’s had an excellent working relationship with his landlord. 

“I own the building,” Proto said of Head Start Haircutters. “I don’t have the overhead that he has. Even if I retire, someone else can rent it.”

But with each passing year, one question looms larger on the barbers’ minds: Who will they pass their businesses off to? 

“I don’t have a second,” Proto said. “Rich and I’ve talked about it. A lot of these young kids don’t want to work for anybody anymore. It doesn’t take a lot to get into business. You get a place, you buy some equipment and you’re off and running. Nobody wants to work for anyone else when you can work for yourself.”

Another issue, Proto said, is clientele. While his booking calendar tends to fill up, Proto said there isn’t enough business to add another person on staff.

“I’m hoping that some young guy will come in and say I’m looking to become a barber,” Santanelli said. “I’ll work with him and in two years I’ll give him the business. If that doesn’t happen, I may end up at Frank’s a couple of years. I want someone I can talk to and relate to. This is a men’s shop. The first thing someone says coming in is, ‘Tell me a joke.’ There aren’t a lot of clean jokes.”

Rich Santanelli cuts customer Jimmy Pascale’s hair at Tony’s Barber Shop in Madison (CT Examiner).

A “men’s shop” fits the masculine aesthetic of both businesses, with Head Start Haircutters decked out in sports memorabilia and encased signed jerseys from athletes like Kareem Abdul-Jabbar, Kobe Bryant, Joe Montana and Jerry Rice.

“The Brett Farve shirt and Emmitt Smith helmet,” Proto said, “I bartered haircuts for them.”

Former NFL tight end Russ Francis, who played for the New England Patriots and San Francisco 49ers was a regular customer, he added, who signed a jersey and card that are also on display.

Tony’s Barber Shop, on the other hand, is nautical-themed, with images of ships and sailing paraphernalia dressing the walls. 

“It was one of two things,” Santanelli said. “I was big into sports. Tony was not.”

The shops also share a rule: “You don’t talk about politics, you don’t talk about religion, and you don’t talk about other people’s wives,” the barbers said.

While Proto and Santanelli found their way to Madison and pursued a career in barbering, their journeys into the trade differ greatly. 

For Proto, it was a family affair. 

“My grandfather was a barber,” he said. “My uncle was a barber until four years ago. My father was a barber and he hated the business and left it.”

Proto initially worked for the previous owner, Gene Calzetta, who then sold the business to him.

Meanwhile, Santanelli became a barber because of the Vietnam War. He said he was drafted but, because of back issues, was only qualified for service in times of war or national emergency. 

Santanelli recalled employers at the time wouldn’t hire him due to his draft status, so he decided to enroll in barber school at Bullard-Havens in Bridgeport.

It was during this time in the late 1960s and the early 1970s, he said, that barbershops started losing their luster, eventually leading to the school dropping the barber program.

“I think it affected the barbering business in the late 1960s and 1970s as guys were coming back from Vietnam and they weren’t getting haircuts, and then the hippie movement started,” Santanelli. 

Though neither man has any prospects for a successor, their businesses still hold steady. Proto and Santanelli said their calendars remain full and that most customers are regulars. 

“A lot of my customers are friends,” Santanelli said. “They’re acquaintances. People you love to talk to. If you don’t like people, this is not the job for you. They like to come in. They like to talk about sports, especially local sports. They like that it’s in the center of town.”

Kevin Cassidy said he’s been going to Head Start Haircutters since he moved to Madison in 2008.

“I like Frank,” he said. “We get along. He’s fun to talk to. He gets it right. I don’t rotate with somebody else. He knows what I want, he does it.”

Tony’s Barber Shop at 708 Boston Post Road in Madison (CT Examiner).

Cassidy pointed out the nostalgia of going to a classic barbershop with the iconic candy-striped pole at the entrance.

“This is what I remember as a kid, going to the barber,” he said. 

Jim Mcewen, whose son recommended Head Start Haircutters, said he likes its convenient location downtown and his job.

“It’s an old-school kind of barbershop,” he said. “It’s friendly, good conversation.”

Jim McNulty said he’s been going to Head Start Haircutters since Calzetta owned the place.

“Gene and I had a deal many years ago,” he said. “He didn’t pay for the snowplow and I didn’t pay for the haircut. It’s been going for 30 years. It’s kind of an old-fashioned barbershop. Across the street it’s the same way. It was always a place to hang out.”

“We’ve been friends for years,” said Tony’s Barber Shop customer Jimmy Pascale, who has known Santanelli for years but only started getting a haircut from him in the past year. “He does a great job.”

Dennis Crowe, who has been going to Tony’s Barber Shop for almost 15 years, said he loves the banter.

“It’s a small town barbershop,” he said. “The entire community and the nature of the town, we’re blessed.”