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Time To Groove

Jessie Baylin’s Strawberry Wind Celebrates Whimsey And Wonder

Article by Christina Madrid

Photography by Provided

Originally published in Franklin Lifestyle

Have you ever had a song stuck in your head? After listening to Jessie Baylin’s deluxe edition of Strawberry Wind, you are bound to have multiple melodies playing in your mind on any given day. There is something about her imaginative lyrics and dreamy production that appeals to everyone.

Music has always played a role in the Nashville-based singer/songwriter’s life. Her parents owned a restaurant and bar in New Jersey, so she was around music all the time. “It was before streaming music, so my mom would put 10 CDs into a CD changer and I would mess around with the shuffler,” says Jessie. Her parents also introduced her to jazz at a young age. Those tunes are linked to some of her fondest memories, so it is not surprising that the tracks on Strawberry Wind reflect that psychedelic warmth of the 1970s.

Jessie left New Jersey to attend art school in New York. She was interested in performing arts and took acting classes. Being surrounded by artists, there was much to explore but it wasn’t until living in Los Angeles that she knew she wanted to sing. Then things started to happen. She booked a showcase and had a residency at a club in L.A. where her show continuously sold out. At 20, she landed a publishing deal with Sony.

Since then, Jessie has had several celebrated albums, but Strawberry Wind is her first family album. Inspired by the joy of motherhood, Jessie pitched the idea of a family album to Amazon, and they loved it. So she and her longtime friend and producer, Richard Swift, got to work on an album that brings out the child in everyone. Jessie also had a short, animated film made to accompany five songs, which follows a young girl’s adventures as she dreams.

Jessie re-released the record in April—a deluxe edition, with four new songs she recorded in December. Even though it lived exclusively on Amazon until recently, it has been her most successful album so far, with more than 23 million streams.“I’m excited to get it into the hands of more families,” she says. “A lot of love and thought went into this album.”

The songs embrace universal themes that anyone can relate to and allows adults to be whimsical. “We didn’t dummy it down for kids,” Jessie adds. The song “Sparkle Shoelaces" for instance, was literally inspired by shoes with sparkle shoelaces, but it also carries a deeper message of how positivity can turn things around, as she sings “what once was tragic turns into magic when you put on your sparkle shoes.”

As if the success of the album wasn’t impressive enough, despite being a mom, an artist and running a household, the Strawberry Wind deluxe tracks were written and recorded in just two days. Jessie admits that she has a knack for songwriting and understands the sound she wants. 

In 2018, Richard Swift passed away and Jessie stepped back to reflect and decide what to do next. She had worked with Richard for over a decade and he helped build the sound she was known for. Jessie stayed in a “safe zone” and wrote with her friends, Daniel Kashian and Ian Fitchuk and came out with Jersey Girl in September 2022.

A lot of the creative descriptive writing she had done for Strawberry Wind was poured into Jersey Girl. “I loved just opening my mind ’s eye as I was exploring an idea- just playing with words in a more descriptive way,” she says.

Jessie, in a sense, came full-circle with the release of Jersey Girl, a nod to her birthplace. “I was running away from that life for so long,” she admits. “I wanted more than living in the suburbs of New Jersey.” But she now realizes, “it is a fine, solid base to grow up from,” and is proud of that album. In fact, the last track, “Jersey Girls,” pays tribute to all those “fierce but soft Jersey girls that are so lovable.”

So what’s next for the artist who set and achieved her two major life goals (opening for Stevie Nicks and selling out the legendary Troubadour-nightclub in California)? “I have some song ideas kicking around,” Jessie says. “I don’t want to wait too long to release another album.” In the meantime, she plans to do some family-oriented shows around the country in unique locations. She believes that children should have the opportunity to see live performances.

Her one piece of advice for all those aspiring artists in the area is to “stay creative and carry a pen and paper with you wherever you go. Songs are everywhere. You just have to pay attention.”