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The Reinvention of Sammy Buttons, Master of Sidewalk Funk

If it weren’t for the pandemic, Sam Pritchard might still be weaving through the streets of Manhattan as a bike messenger. But March 2020 and the subsequent emptying out of office buildings forced Mr. Pritchard, who like many other businesspeople relied on the bustling commerce of Midtown, to pivot.

These days, Mr. Pritchard, now 61, has replaced his bicycle with a keyboard: He is now a street musician, living mostly off donations. From Union Square to Grand Central Terminal, he entertains crowds daily, even capturing the attention of drop-by celebrities like the actor Bill Murray, and of young musicians who now play with him regularly. He calls his show — part dance party, part jam session — “The Sammy Buttons Experience.”

I first met Mr. Pritchard back in the early 1990s, when his upstart bike messenger company was often called in to make deliveries for my public relations firm. He was energetic and fit, an entrepreneurial hustler who logged 50 to 75 miles a day on two wheels. Over the years, Mr. Pritchard’s business grew to a 25-person company with an office on Fifth Avenue. Even though he was the boss, Mr. Pritchard preferred the bike to the desk, choosing to spend his days on the heavily trafficked thoroughfares of Manhattan, ones that currently claim the lives of roughly two dozen bicyclists per year.

But Mr. Pritchard had another passion, more deeply ingrained: Music. He is a fourth-generation keyboardist. His great-grandfather was a noted stride jazz pianist working the circuit around his native North Carolina. His father was an equally talented hobbyist, a purveyor of modern jazz and R&B styles, who in the 1950s moved to Harlem, where he settled down with his wife, who gave birth to Sam in 1961. Three years later, the family relocated to Westchester.

“Like most every Black kid born in Harlem, music was in my blood, even though my family moved away when I was young,” said Mr. Pritchard, who took piano lessons from age 4 until he turned 13. He mentioned Stevie Wonder, Ramsey Lewis, Earth, Wind & Fire, the Commodores and Sly Stone as his favorites. “The infectious energy and swing of these cats is what I try to bring to the streets today” he said. “Funky music is good medicine.”

A Times Square groove with Bernell Jones II, left.CreditCredit…Laylah Amatullah Barrayn for The New York Times

It was a Sly and the Family Stone album, “Stand,” that got Mr. Pritchard into a bit of trouble shortly after his family had moved to the suburbs.

“We were the first Black family in an all-white neighborhood,” he said. “And I was one of only two Black kids in my school, so I felt a bit isolated.” In the fourth grade, he brought the album to a show-and-tell day. The song he played for the class had a racial slur for Black people in the title and in the lyrics. “There was a big hubbub and my father got called to the school,” Mr. Pritchard recalled.

At Howard University, where he was on a basketball scholarship, Mr. Pritchard played some music, and then as a young man in New York, he toyed around in production and jammed at the Lenox Lounge in Harlem a few times with the likes of guitarist and vocalist George Benson and flutist and vocalist Bobbi Humphrey, he said. But his growing messenger business would keep music on the back burner for several decades.

In 2018, Mr. Pritchard met up with a friend and bass player from Detroit, Tony Russell, to jam on the street for fun. Just a few of those sessions were enough to inspire Mr. Pritchard in a new direction. “Tony told me I was selfish not to play on the streets,” he said, “that I had something special to give to the people and myself.”

Mr. Russell died of a drug overdose in 2020, just as Covid descended on New York. Two days after his friend’s death, Mr. Pritchard hit the streets with his keyboard, a Bluetooth amp and a “shopping cart to move it all about,” he said. He wanted to honor his friend, and his friend’s wish for him. “I haven’t looked back since.”

Credit…Laylah Amatullah Barrayn for The New York Times

He plays a mix of original music, soul covers and ballads. “I use drum programs and loops, and lay down bass lines with my left hand, and chords and solos with my right,” he said. “It’s about creating a dance party atmosphere, almost like a D.J. but only with a keyboard.”

By the summer of 2020, Mr. Pritchard was not only drawing crowds, but younger musicians who wanted to play with him.

“I met Sammy when I moved to New York in 2017,” said Benny Rubin, 22, a saxophonist from Flint, Mich. “He saw me playing in the subway and invited me to jam at a free festival.” They ended up playing together every day during the summer of 2020 and into the fall, which helped Mr. Rubin “financially and spiritually,” he said, since his club gigs had been canceled because of the pandemic.

“The experience was cool because I am into more serious, straight-ahead jazz, and he’s all about soul and funk and getting a party going,” Mr. Rubin said. “It’s cool to be around Sam because he has a lot of life wisdom too. He has taught me about way more than music.”

Another saxophonist, Bernell Jones II, played with Mr. Pritchard every day last summer. “I’m from Memphis, so I’m into heavy soul and R&B, so we really connect,” he said. “He’s in his 60s and I’m 23, but somehow we’re best friends,” he continued. “Sam has always had a business mind-set and a knack for scoping out all the best little places to play and gather a crowd. It’s one that’s been able to turn this into a full-time job for both of us.”

Fans range from 3 to 80 years old. Last summer, Bill Murray came by. “I said to him ‘You owe me $20.’” Several years ago, according to Mr. Pritchard, he was making a delivery and saw Mr. Murray waiting to retrieve his car at a lot. Mr. Pritchard bet the actor $20 it was going take him more than 20 minutes to get his vehicle. “When I swung by after the delivery 30 minutes later, he was still there waiting.”

CreditCredit…Laylah Amatullah Barrayn for The New York Times

That day, he told the story to Mr. Murray, who smiled, said he thought he recalled the exchange, and put a $20 bill in the tip jar.

Another time, Senator Chuck Schumer, Democrat of New York and the majority leader, stopped to listen at Union Square. “I told him we needed to have a serious conversation about gun control, especially those AR-15s.”

The police, instead of making him pack up and leave, often stick around to enjoy the music, said Mr. Pritchard, who added that he has befriended many of those who patrol his regular spots.

Recently, Mr. Pritchard has started performing at weddings, corporate events and clubs. This month, he will embark on a 10-day residency at the Sound View hotel in Greenport, at the far end of Long Island. In a good week, the Sammy Buttons Experience can bring in four figures. This year, he plans to invest some of that in recording his original music and in starting a line of merchandise.

“As horrible as Covid-19 has been for so many of us, I know it was the thing that pushed me to do what I always wanted to do, to entertain people with soulful music that spreads joy,” Mr. Pritchard said. “If I have played some small role in helping New Yorkers deal with the tragedy that Covid has brought, it’s all worth it.”

Sal Cataldi is a writer, musician and former public relations executive based in Saugerties, N.Y.

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