Beacon guitarist has gig at Empire State Building
Four years ago, Tony DePaolo’s musical career reached new heights: an employee impressed by his guitar playing on a glass-enclosed party boat off lower Manhattan and recommended him for a regular weekend gig on the 86th-floor observatory of the Empire State Building.
From the time he graduated from Beacon High School a year early, DePaolo has made a living playing music. “I spent what would have been my senior year learning the ropes of how to craft a career,” he says. “The worst thing I could do is say ‘No’ to a gig; I always say ‘Yes’ and figure out how to get it done.”
He’ll take a typical $100-per-musician bar gig, but by working his connections and staying true to the tunes, he also has opened for six-string idols Larry Carlton, Steve Morse and Stanley Jordan. A jazz fusion fan, he debuted for Spyro Gyra, one of the genre’s biggest bands.

DePaolo lives in the Beacon house where he grew up, across the street from his elementary and middle school, St. John’s, where the nuns nourished his musical talent from a young age.
“I give them credit for instilling that discipline,” he says. “My father played piano and for him, music had to be done right. I had to read music and practice, and it all paid off.”
He started on the keys, but like many impressionable young people at the time, he watched The Beatles on The Ed Sullivan Show in 1964 and begged his parents for a guitar.
In 1999, his wedding combo got a boost after appearing in two episodes of the first season of The Sopranos. “Every couple in New Jersey wanted us,” he recalls. He also appears in the Chaz Palminteri film Once More with Feeling.
Although DePaolo shares a birthday with guitar pioneer Django Reinhardt, who died in 1953, he’s versatile and fronts a Jimi Hendrix cover band, Electric Gypsies. His signature style is arranging lush jazz versions of popular songs from the Great American Songbook to today’s Top 40.
One thing he never got into was digital production. “You have to get everyone in the room together and record live — like they did at [classic jazz label] Blue Note Records,” he says. “No one wore headphones. If they didn’t get the take, they had to play it again.”
In 2014, he released an album of covers and three originals. He and videographer Jon Slackman made a short with drone shots of Fishkill Creek.
Over the years, De Paolo played a dizzying number of recording sessions. One recent project is backing Woodstock-based singer Lindsey Webster, who topped the Billboard Contemporary Jazz chart with the singles “Fool Me Once” and “Where Do You Want to Go?” — a rarity for vocalists in that category.
Staring out the window toward his old schoolyard, DePaolo recalls seeing photos of his young self as a prodigy in the Beacon Free Press and the now-defunct Beacon Evening News, along with the days when the city’s music scene continued into the wee hours.
“I was playing out four to six nights a week — there were 20 places from the river to the mountain,” he says. “Now, I come home after the Empire State Building around midnight, and there’s nowhere to go for music.”
DePaolo will host a free Last Waltz tribute at Quinn’s in Beacon at 8 p.m. on Wednesday (Nov. 27) and perform at the Silk Factory in Newburgh from 11 a.m. to 2 p.m. on Sunday (Dec 7).