(Photo courtesy Benny Benack III)

On the eve of his 30th birthday, Benny Benack III, a Pittsburgh-born, New York City-based trumpet player, jazz singer, pianist and charismatic bon vivant played a late November show at The Craftsman, a plucky bar in Morningside Heights. Cold rain fell staccato against the patio’s plexiglass roof while patrons, mostly masked, huddled around stanchions and heat lamps. From behind a makeshift stage, Benack cracked jokes about his age, his rising inebriation, and called on familiar musicians from the crowd to join the jam session. 

Beneath a nearby awning, Aaron Johnson, an accomplished saxophonist and Benack’s periodic bandmate, chuckled at his friend’s antics.

“Don’t let his laughs and smiles deceive you,” he said. “He’s a very serious musician. The music he plays and the notes that come out of his instrument are absolutely cannon. It’s like hearing a record from the ’50s.”

Of the many jazz musicians who call New York City home, Benack is one of the few who made the most of a disastrous 2020. Last year, the jazz scene’s infrastructure — an ecosystem of clubs and venues that artists rely on to earn a living, establish their name, and build community contacts — essentially collapsed. Feeling as if the house had crumbled around them, many musicians spent the first few months of quarantine feeling disoriented and unproductive. But Benack got to work. He recorded songs in his West Harlem apartment, cultivated his social media presence, appeared on podcasts and sought venues, as soon as it was permitted, to perform outdoors.

“Everybody was in the same boat,” he said in a phone interview. “And once I realized that, it was a matter of refocusing and saying, All right, well, if everybody’s doing the same thing, sitting at home, what can I do to stay in the race?”

On the Sunday leading into New York City’s lockdown, Benack played a show at The Craftsman. The next morning, on the first day of quarantine, a song he had performed — “Put On a Happy Face” from the 1960s musical Bye Bye Birdie — returned to him. He reimagined the lyrics (“Don’t spread corona all over the place / And put a mask on your happy face”), set up a camera opposite his keyboard, pulled on a striped shirt and grey blazer with a pocket handkerchief, and recorded a cover, “Put a Mask on Your Face.” He jammed through the song, playing, at one point, both trumpet and keyboard simultaneously. He uploaded the video to YouTube, where it continued gathering hits until it was picked up by a local news network. It’s since gone viral, accumulating thousands of views. 

“It was the first day of quarantine and I was still, you know, kind of positive,” he said. “I would have a hard time doing something like that now with over 250,000 deaths in the United States.”

The experience taught him a lesson: it was possible to stay relevant, as a jazz musician, during the pandemic. It would just require creativity.  

Benack is a dapper dresser, preferring sport coats and blazers, of medium build, and has a young face masked by a well-maintained beard. He is the son of Benny Benack II, a renowned saxophonist, and the grandson of Benny Benack, a legendary trumpet player, who once showed Fred Rogers how to play the instrument on an episode of Mister Rogers’ Neighborhood.

That Benack III plays the trumpet, like his grandfather, is no coincidence. In a jazz band, the trumpet and the saxophone are considered complementary instruments. They can share the stage without stepping on the other’s toes. Gaming this dynamic, the Benacks orchestrated a generational tradeoff. 

“My grandfather didn’t want his son to play the same instrument so they could play gigs together,” Benack said. “So that’s why my dad plays the sax, and wanted me to play the trumpet so I could stand next to him on stage.”

The trumpet, whether by chance or by a lifetime on his lips, is also a dead-on match for Benack’s personality. In the mythology of jazz it represents “the natural leader in a group of individuals,” explained Juilliard-trained bassist Russell Hall, another of Benack’s regular bandmates. It’s often a band’s loudest instrument, and players who gravitate to it tend towards extroversion. Louis Armstrong played the trumpet, as did Miles Davis and Dizzy Gillespie — figures whose instruments became inseparable from their identities. 

Benack, however, attributes his confidence and charisma to his mother, a voice teacher at Carnegie Mellon in Pittsburgh. She often taught private lessons at their home, and as a child, Benack would rise on weekends to the sound of her students singing — and her giving feedback. 

“‘Make sure you’re making eye contact with your audience,’” he recalled her saying. “‘Get your hands out of your pockets and really tell the story of the song when you perform it.’”

But his formal introduction to jazz — and the world of freelancing — came from his father.    

Benack started singing at age 5, and playing trumpet at age 9. His father, during those years, would often call him on stage to perform a song or two. By age 11, Benack started showing promise as a trumpet player, and his father began hiring him as a bandmember. Some of their performances, particularly one at Greenbrier, a resort and casino in West Virginia, introduced him to the rituals behind the music: driving in a van to the gig, staying up late with the band, playing cards into the early hours. It was a lifestyle as much as a career, and Benack took to it quickly. 

“I didn’t have to spend a lot of time figuring out who I was or who I wanted to be, or what music I wanted to play, or what kind of artists I wanted to be like,” he said.

Those formative experiences produced a strong sense of self, which helped him navigate the bustle of New York City’s jazz scene when he arrived, at age 18, to study at The Manhattan School of Music. After graduation, he played occasional gigs at weddings and birthday parties, but has been able to make rent without private events for several years. 

(Photo courtesy Benny Benack III

When the pandemic shut down the city, his sense of purpose kept him grounded while others felt scrambled. Still, it was a difficult time for Benack, whose career had just hit an upswing. 

“I don’t really want to dwell on what my plans were for 2020,” he said. 

In January, he released his second album, A Lot of Livin’ To Do, which garnered glowing praise in jazz publications like DownBeat and JAZZIZ Magazine, and climbed to number eleven in the Jazz radio charts. Several of his songs accumulated hundreds of thousands of plays on Spotify, and he had tours lined up across the US, Europe and Asia. But in February, when the virus started to spread within China, a three-week residency in Shanghai was canceled. In March, his European and US shows were pushed back, and by April they were all called off. 

In retrospect, the success of “Put A Mask on Your Face” seems timely. Energized, Benack turned his bedroom into a recording studio. He bought a microphone, video editing software, and programs to mix and master his music. He organized remote recording sessions with other musicians — “almost like the Brady Bunch, with everybody’s face in a little square.” Then, over the summer, when Black Lives Matter protests erupted across the nation, he began to perform during protest marches with Russell Hall and other local musicians. 

“The music created an atmosphere of social gathering and joy,” said Hall. “It was a source of protection for people, because when you’re marching without music, then to the police and law enforcement, they see it as more of a threat.”

For many local musicians, the protest marches were the first time they had played with a live band since the start of the pandemic. It was an emotional reunion, Benack recalled, and he began to search for more opportunities to play with friends. 

Richard Agudelo, a professional music photographer and the owner of Terremoto Coffee in Chelsea, befriended Benack just before the shutdown. During quarantine they exchanged texts and DMs, and when the city issued permits for outdoor dining, he suggested Benack perform at the shop. Agudelo laid a patch of astroturf outside of the door, and on the third weekend of June, Benack played the first of what would become an unofficial weekly residency. It attracted dozens of guests and other musicians who had been out of work.

“Benny is like the mayor of the jazz community in New York,” Agudelo joked over the phone. “As soon as he declared the show on social media, everybody came out.” 

Now, with arrival of winter and coronavirus rates rising, Benack said he plans to continue streaming performances, recording in his apartment, and trying to recreate the sense of community that was lost this past year — while still playing outdoors, as long as safety and weather permit. 

“The only way to lose the game is to quit,” he said. “That’s true about New York City no matter what you do, but especially for musicians.”