“It’s got a really unique sound to it. I think he’s paving the way for a new genre.”
Boston-based artist and producer Leo the Kind created his first beat on a PlayStation when he was nine. Now 25, he’s won 2020’s Boston Music Award for Pop Artist of the Year. Joshua Jackson, professionally known as Leo the Kind, fuses pop, R&B, alternative, rock, funk, and electronic influences to create his distinct, eccentric sound. His stage name comes from mixing his zodiac sign, Leo, with the phrase “one of a kind” because he strives for individuality.
Last year he released his debut EP, The U.G.L.Y., with the help of Grammy-nominated producer Keithen “Bassman” Foster and Grammy-winning producer David “Swagg R’Celious” Harris. Dripping with innovation, thoughtfulness, and a wide variety of musical styles, the warm, clean production melts the tracks into a cohesive piece of art.
Growing up in Dorchester watching his cousins rap over beats inspired Leo to take up music. They used a PlayStation game called Music Maker to throw loops together and shape them into a beat. “I watched them do that over and over to the point where they wouldn’t be home and I’d sneak on it and try to make some beats,” said Leo.
After that, at about 12 years old, Leo started teaching himself piano by ear.
When he moved to Brockton for high school, he was surrounded by other artists and wanted to make beats for them. However, he only had Music Maker as a resource to produce. So, his dad figured out how to rip the audio from the game, and Leo’s producer career began using beats from PlayStation.
At 15, Leo’s dad took him to a recording studio to introduce him to an artist manager he knew. Soon after, Leo started producing for one of the artist manager’s groups. “They had brought me to an actual music studio, and it was my first time there. I was talking to the engineer and I was like, ‘You get paid doing this?’ And he was like, ‘Yeah.’ ‘Like you live off of this?’” asked Leo. “He’s like, ‘Yeah.’” In this instant, Leo knew making music was his future.
In 2016 Leo taught himself guitar then picked up singing from YouTube. For two years, he watched the same video every day to learn vocal scales and how to warm up his voice. “I did that until I got my voice to a point where I was comfortable, and then I started putting music out,” said Leo.
Music journalist Lennon Cihak has seen Leo’s sound evolve over the years. “He’s got this funk with this classic rock with this EDM mixed with trap and then his vocals are just so warm—it works so well,” said Cihak. “It’s got a really unique sound to it. I think he’s paving the way for a new genre.”
Cihak especially likes how Leo lets the production details shine through, noting the cool static, percussion elements, and layered vocals in “Ain’t Nobody Gon’ Judge.”
Songwriter and producer Keithen “Bassman” Foster helped write and produce that single and The U.G.L.Y. He’s been mentoring Leo on his music for a few years, but they first met eight years ago at church. It was Leo’s confidence in his creativity and individuality that captivated Foster.
“The way he carried himself and his boldness and his hunger to want to learn and want to know more just intrigued me. He already knew what he wanted to be,” said Foster. “That alone already sparked enough interest for me to listen to anything he had to say.”
After Foster checked out his music, they started sending each other production ideas and developing his unique sound. This led to Leo being invited to help engineer a recording session with Bassman’s production partner, Swagg R’Celious.
So, in his first trip to Los Angeles, Leo found himself in a room at West Lake Studios in between Trey Songz and Usher. Established writers and producers were flowing in and out of the rooms. They made a couple of production ideas, and Bassman told Leo to jump in the booth to lay down a melody idea.
“He went in the booth and—the melody he had for the top line—everybody in the room just turned around was like, ‘Wait, what?’” said Foster.
They all started working together and building up a catalog. Leo sent them songs for feedback, but Foster admits, “Most of the time we don’t need too much critiquing when it’s writing because he’s really dope as a writer.”
Most recently, Leo, Bassman, and Swagg have been creating a mixtape, entitled Sorry Miss Jackson. It’s Leo’s largest project and will be released later this year. The lead single, “Fake Love,” comes out in April.
Despite a busy year ahead, Leo still has massive career aspirations with one of them being to take home some Grammy Awards. After that, he wants to start a music production school for kids and teenagers.
“I really want to open some sort of school that allows people to create because I had to do it in such a weird way growing up, like I was making beats on a PlayStation,” said Leo. “I want to provide kids a space where they can create with real technology and professionals.”