“Patience, patience,” Mr. Calabrese advised while trimming the boy’s wispy blond locks. “You have to stick with them and wear them out.”

The goal of first haircuts is simple: Get the child through it without tears or tantrums.

Little Mark had a bit of a leg up on other kids. Last time his dad got a haircut, he tagged along to get comfortable with the sights and sounds of a barbershop. Mr. Calabrese gave his bangs a few snips.

Over the years, Mr. Calabrese has learned how to handle fidgety young customers. He has a pile of pictures of kids after their first haircuts – most smiling, only a few scowling.

With Mark sitting on the lap of his dad, Mark IV, Mr. Calabrese first snipped air over the boy’s head, just to get him used to the sound. Then he gently started trimming near Mark’s right ear.

“Markie, it’s okaaay,” cooed Maria Perkins, the tot’s mom.

By the time he moved to Mark’s bangs, the youngster looked worried. He tried to turn his head away, but Mr. Calabrese coaxed him to hang in there.

About 32 years ago, it was Mark IV getting his first haircut from Mr. Calabrese, one of the city’s best-known barbers.

“I think he was all right,” Mr. Calabrese said, and Mark III agreed.

It was Mark III – little Mark’s grandfather – who discovered Mr. Calabrese’s skill with the scissors and razor in the late 1960s. He worked at a car dealership next door to the barber’s old shop on West Street, and convinced his father, Mark II, to get his hair cut there too.

Over the years, the Perkins men have moved from Annapolis, but they always kept coming back to Mr. Calabrese every six to eight weeks – even as he kept moving to different shops. “I always had a good business, but no place to put it,” he said.

In an age where fancy salons and discount chains dominate the hair-cutting landscape, Mr. Calabrese’s station inside the three-chair Eastport Barber Shop is something of a throwback. It’s kind of like the TV show “Cheers” – everyone knows your name.

“Sometimes it dawns on me that everyone here is an Annapolitan,” Mr. Calabrese said. “But then you go to the mall and you don’t know anyone.”

Mark IV, 33, never tires of Mr. Calabrese’s barbershop chatter.

“He’s interesting to talk to. He always has good stories,” he said.

Over the years, Mr. Calabrese has shared his wisdom about ATVs, hunting and the way Annapolis used to be. And he should know – he’s been barbering for nearly 56 years after starting as a teenager in his dad’s shop.

Mark V isn’t old enough yet to appreciate the stories, but is just old enough to experience the barber’s swift but gentle snipping.

After a few minutes of trimming, Mr. Calabrese looked back at his work in progress and checked with mom: “Maria, does that look all right in the front?”

Mrs. Perkins gave her approval as Mark sucked in his bottom lip and furrowed his brow.

Sensing that Mark was close to breaking down, Mrs. Perkins handed him a short broom the boy played with while waiting. Mark nearly dropped it, resulting in a torrent of giggles. Crisis averted.

Later, as Mark fidgeted while Mr. Calabrese worked on the back, Mark IV improvised and played peek-a-boo using a handheld broom.

Finally, the drama was over. Little Mark lost a couple of inches of hair all around, most of it put in a white envelope for safekeeping.

The family posed for pictures with their favorite barber – one more to add to Mr. Calabrese’s collection at the barbershop.