Become a member and get exclusive access to articles, live sessions and more!
Start Your Free Trial

Tony DeSare: Radio Days

Where will 10 years of violin lessons, a Sinatra cassette and a business degree get you? For vocalist/pianist Tony DeSare, it was enough to take him to the very top-literally. The violin lessons began when DeSare was 8. He discovered the Sinatra tape, a collection of seminal Capitol hits that opened up a whole new world of music for DeSare, when he was 14. The degree was earned in the mid-’90s at Ithaca College.

Like so many eager twentysomethings armed with a biz diploma, DeSare headed for Manhattan. And, in 1998, he did land on Wall Street, but not as a trader or analyst. Having decided, against the protests of his Ithaca professors, to aim for a career as a crooner and piano player, DeSare found himself an agent and was immediately granted a gig at Windows on the World, high atop the World Trade Center. “It was,” DeSare recalls, “a one-nighter that really didn’t pay anything, but it was my first official New York City appearance and it made me realize what I was up against to try and make a career of this.”

After three months of “stuffing envelopes” as a temp, DeSare earned a spot with the band at another Manhattan high mark, playing five nights a week in the 44th-floor lounge at the Marriott Marquis in Times Square. He then won an understudy role in the off-Broadway production of Our Sinatra (another up-and-coming singer-pianist, Peter Cincotti, would follow him in the cast), strengthened his Sinatra connections by playing at the reopened Jilly’s of New York, found a friend and mentor in comedian (and celebrated Sinatra impersonator) Joe Piscopo, cut a demo with Bucky Pizzarelli and, in 2005, found his way onto the Telarc roster.

DeSare’s first two Telarc releases, 2005’s Want You and 2007’s Last First Kiss, revealed a performer who, blending the best qualities of Michael Bublé and Harry Connick Jr., can swing like Sinatra or Bobby Darin on hipster anthems like “Baby, Dream Your Dream,” “Come on Strong” and “We’ve Got a World That Swings,” but is equally comfortable with material from the Carole King, Dylan and Prince songbooks. Of the quasi-retro vibe that pervades DeSare’s work, he says, “People often ask if I’m trying to bring back a certain era or if I think I was born too late, but this is simply a specific way of putting across music that has lots more room for exploration. It’s not retro. It’s a statement about 20th-century American pop, but it also points forward, making the case that different takes are possible on songs the people might otherwise not have thought could survive the transition from the rock-pop ’80s to a big-band swing arrangement.”

DeSare’s latest album, the recently released Radio Show, extends his era-shifting skills by crafting a faux radio program, complete with deejay intros provided by Piscopo, that follows a circuitous route from the 1940s to the ’80s. “I got the idea about a year ago,” he explains. “I love the [Sinatra/Darin] style of music and there are many talented people doing it, but what I felt hadn’t been done yet was to take a cue from hip-hop recordings that use elements from different musical sources to put together a show. I’m not a huge fan of hip-hop or rap, but I respect the originality of those artists and their drive to do something new. They really build a show and make each CD a flowing experience. I started wondering how that could be done in this genre, and it got me thinking that most people know these songs from hearing them on the radio. So the idea became to build the album around a radio experience and take the listener on a journey, almost like you’re on an hour-long drive, switching stations and looking for your favorite songs.”

Radio Show travels from such Great American Songbook classics as “Get Happy” and “All or Nothing at All” into the rock era, finally landing in the ’80s with distinctively clever covers of Phil Collins’ “Easy Lover” and New Order’s “Bizarre Love Triangle” (on which DeSare is ideally paired with Jane Monheit). In addition to these inventive interpretations, the album demonstrates DeSare’s continuing growth as a songwriter. Blessed with a remarkable ability to construct tunes that rival the best of Sammy Cahn, Jimmy Van Heusen and Cy Coleman, DeSare says, “There’s a tendency among people who write in this style to try and write something that’s retro-sounding, and to try and recreate the lingo of another era. But I approach it from a modern perspective. So when I write a song like ‘A Little Bit Closer’ [from Radio Show], I’m doing it from my perspective as a child of the ’80s. I’m not afraid on my songs to use current references like ‘turn off your phone’ [from “Let’s Stay In” on Last First Kiss] or Abercrombie & Fitch [on “If I Had Drew” from Want You]. Also, if I’m going to include an established standard written by a great songwriter on a CD and the next track is a song written by me, my strict standards demand that my song be able to hold its own in context.”

With three albums under his belt and his audience rapidly expanding, DeSare says he’s “finally starting to feel my power as a singer and performer, and I want to see how far it can take me.

“I simply want to share my music with people who want to hear it. Whether that ends up being Radio City Music Hall or a 50-person club, that’s OK, as long as I get to do this for as long as I possibly can.”

Originally Published