Home from Nashville

Westport’s Aaron Lessard teams up with Stephanie Adlington for June 12 show

By Kristen Ray
Posted 5/29/19

Over a thousand miles away from the Massachusetts shoreline, right in the heart of Music City, Aaron Lessard has been, as he phrases it, non-stop hustling. In the year and half …

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Home from Nashville

Westport’s Aaron Lessard teams up with Stephanie Adlington for June 12 show


Over a thousand miles away from the Massachusetts shoreline, right in the heart of Music City, Aaron Lessard has been, as he phrases it, non-stop hustling. In the year and half since moving out to Nashville, the modern vintage rocker and 2014 Westport High School graduate has dropped his debut EP, album, Sex Jive Rock N’ Roll and played in Whiskey Jam, a live original music showcase that has seen the likes of OneRepublic and Kip Moore share its stage.

In the coming weeks, Mr. Lessard will be releasing his new single, “Throwback Kind of Woman,” but before he sets his sights on releasing a full album this fall, he will make a return to his roots with a homecoming rock-and-jazz fueled performance alongside award-winning jazz vocalist Stephanie Adlington at the Narrows Center for the Arts on Wednesday, June 12 at 8 pm.

The early days

The winding path leading up to this point in Mr. Lessard’s music career began right at home here in Westport. In the days before YouTube and streaming services made it almost too easy to discover new bands and artists, his exposure to music was mainly from the rock and live concert tracks his parents played over their house’s surround sound system.

“I was still listening to a lot of older music; that's what my ears’ always gravitated towards,” he said.

When he reached fifth grade, Mr. Lessard picked up the guitar, enrolling in lessons under Patrick Cardeiro at what is now called Double Bar Music. It was there that Mr. Lessard was first introduced to jazz concepts, something that he still incorporates into his music today. As he continued on through the Westport school system, teachers Chris Nunes and Sammy Costa helped keep his passion for performing afloat during a time when the town’s funding for the music program was dwindling.

By the time that he began attending Berklee College of Music camps in high school, Mr. Lessard knew that he had found what he was meant to spend his life doing.

“I found that at the end of my time there, I realized that I had the drive and ability to grow into the musician I hoped to be,” he said.

Armed with an eclectic mix of musical influences ranging from Eddie Van Halen to Al Holdsworth to Billy Joel, Mr. Lessard headed off to Berklee, ready to take on that the next step in his musical journey.

Times of transition

Before college, Mr. Lessard had fully expected to one day make a career out of writing and playing jazz. Early on in his Berklee days, though, he discovered that path was not for him, and, upon graduation just three years later, he returned home to figure out his next move.

Though Westport was “a great town to grow up in,” Mr. Lessard said knew he could not stay in his hometown if he wanted to keep growing as a musician. Wary of Los Angeles’ overwhelming focus on electronic beats and studio recordings and uneasy about New York City’s lack of a music-industry identity, he settled on Nashville, where he felt his inherit music stylings might be best appreciated.

Despite hardly knowing a soul in town, Mr. Lessard took the leap and made the move to Music City in Sept. of 2017. Once settled in, he vowed to make a return to writing rock music without dropping the jazz concepts that had so intrigued him for the last decade.

“I thought to myself, how can I write rock music but in a very catchy way?” he said.

The answer came to him through the stylings of prominent songwriters like John Mayer, 50s rhythmic rock tunes and the rockabilly revival group Stray Cats. Those influences helped shape what would become Sex Jive Rock N’ Roll, recorded exclusively on vintage tape and released in July of 2018.

While the EP was featured on Lightning 100, Nashville’s premier independent radio station, Mr. Lessard came to fully appreciate just how difficult making a living in today’s music industry can be. In an age where he feels it is more about the people you know as opposed to the talent you hold, Mr. Lessard has found himself self-financing a lot of his own marketing and branding throughout the entire process. For him, it has become figuring out ways to smartly self-promote while surrounding himself with like-minded people.

“Today, it’s just about grabbing who’s invested in you and building a community around that.”

Returning home

One of the most influential people Mr. Lessard has encountered in Nashville just so happens to be one of the first people he even met, Ms. Adlington. Dubbed “The Siren of the South,” Ms. Adlington, at one time an opera singer, recently won the title of “Best Jazz Vocalist” by the Nashville Industry Music Awards.

“She’s been a great friend to have, a standard to hold you and others to,” Mr. Lessard said.

Bonding over their respective transformations over the past few years, the pair decided to join forces for the next phase of their musical journeys, combining his vintage rockabilly, her sultry “Jazzicana,” drums and an upright bass for what they hope will develop into an intimate New England tour this summer. In preparation for their show at the Narrows, Mr. Lessard is in the midst of writing new music, hoping to debut six new songs as they collectively explore this new concept together.

“This show is cool,” Mr. Lessard said. “It’s a hometown show incorporating these new things. It’s a test run.”

Tickets for the show are $19 in advance and can be purchased from the Narrow’s website. To stay up-to-date on promotions and other information, Mr. Lessard welcomes community members to friend him on Facebook and follow his Instagram @aaronlessardguitar.

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