Leon Silva has played saxophone on recordings for Ariana Grande, Mary J. Blige, Lady Gaga, Michael Jackson, Coldplay, the Mighty Mighty Bosstones (a band he was a member of for eight years), and Justin Timberlake, who he is currently on tour with. During a break in the world tour last month (yes, that tour, but more on that highly-memed moment later), Silva took a moment to post an Instagram story, showing pride in an achievement that just may rival his aforementioned accomplishments.

“This tour with Justin Timberlake is so phenomenal and so fun,” he says, introducing the video, “that I almost forgot to post this very, very special moment, 20 years in the making.”

With his family looking on, Silva opens the mail and does a triumphant dance to a Barry White song as the camera reveals a diploma with his name on it from Berklee College of Music. As the video concludes, he holds up the piece of paper and does a proud sigh, as a voiceover tells his followers, “it’s never too late; don’t give up.”

Silva’s Berklee journey began in 1999, on a scholarship to study music education. He left in 2003, about a dozen credits shy of a degree.

“I think I had one of the golden ages of Berklee when I was first there,” he says. “Because this was before Pro Tools and stuff was really getting popping, so we still had a lot of musicians that were really just focused on the craft of learning music. I was there at the tail end of John Mayer. I got there and Rashawn Ross was there, Jaleel Shaw, Walter Smith, who’s teaching there now. I studied under Bill Pierce, Walter Beasley, George Garzone, so that network was amazing. There were some really great cats there when I was there.”

After leaving Berklee, Silva taught music in Massachusetts for a while before moving to Los Angeles with a pair of fellow Berklee alums, aiming to become the horn section for a gospel artist. When that gig fell through, Silva, trumpeter Sean Erick, and trombonist Kevin Lloyd Williams Jr. decided to stick together and call themselves the Regiment Horns.

“We started hitting the streets, playing all the clubs, just jamming,” Silva says, “and through that we got called in to do some studio sessions. During that time we worked with another cat that was from Berklee named Theron Feemster, who goes by the producer tag Neff-U, and he locked us up with Mary J. Blige and Ashanti, and so we caught a lot of records for them, got some Grammy nominations and all that. We were just babies!”

The studio gigs kept coming, including some sessions with Justin Timberlake, who liked the Regiment Horns’ sound so much he tapped the trio to go on tour with him. Leon began picking up gigs with other artists when Timberlake wasn’t touring, and found himself on Jimmy Kimmel Live, playing with the band Miike Snow, a performance which led to a tenure in the Mighty Mighty Bosstones.

“I was walking off the stage, and Dicky Barrett, the announcer for Jimmy Kimmel [and singer for the Bosstones] comes up and taps me on the shoulder, and he’s got this real husky voice, man, and he says, ‘Hey, man, I heard you’re from Brockton, Massachusetts.’ So I was like, ‘Who the hell is this guy?’ He was like, ‘I think I have a job for you.’ And then we just got to talking. And yeah, I did that for eight years.”

Silva has played some enormous venues with big acts, so does that mean the club shows with the Mighty Mighty Bosstones were easier? Not at all!

“I’m nervous every night,” he says. “I don’t care if there’s two people in the audience, or if it’s 30,000. … I would be in these five-star hotels with the biggest pop star in the world, and then I’d get a break, and I’d go off with the Bosstones, and we were hitting like Motel 6s … but oh my God! Their fan base was incredible!”

Silva also had some great times incorporating his family into the mix with the Bosstones.

“My daughter came up and played with me one time. She’s a vocalist, and her artist name is Léa the Leox, and she went to Berklee as well. But she came through high school playing trumpet. So we did the Hometown Throwdown [the Bosstones’ annual string of local shows in Boston]. And I was like, ‘Hey, guys, let’s get her up there!’ So that was such a great moment, and then on Jimmy Kimmel, we did the show there, and my son, who was six or seven at the time got onstage with us. He was skanking with us all night long.”

Silva plays with the Mighty Mighty Bosstones on Jimmy Kimmel Live! as his son skanks along.

Throughout his varied career, Silva says finishing his degree was always at the back of his mind. Then when lockdown hit in 2020, he knew it was his chance.

“I like to explain to people that I had kind of an existential crisis in those moments, because I was like, ‘Damn! What do I do outside of music, playing the saxophone, playing on other people’s stuff?’ So I had to get myself together.”

Silva connected with an advisor in Berklee’s Alumni Degree Completion Program and started taking classes with Berklee Online.

“Over the course of 20 years the courses changed, and the education track changed,” he says. “So some of the courses that I had taken before weren’t even relevant to what’s needed now for an educator.”

Silva says the convenience of taking courses with Berklee Online was a major plus. 

“I live in Los Angeles now, so I didn’t have to uproot myself and get back to Boston,” he says, “so that was super super helpful.”

But once he got his diploma he made sure to pay a special visit to his family, especially his parents, who he says “busted their asses to help” him on his college journey.

“I actually hadn’t seen my parents face-to-face in about four years previously,” he says, citing the pandemic, health concerns, and scheduling conflicts. “So they were coming to the [Justin Timberlake] concert. It was their 45th anniversary, and so I gave them that diploma on that day. They had no idea it was coming!”

‘What Tour?’ … ‘The World Tour.’

While we want to celebrate Leon Silva’s achievement, we couldn’t help but ask: When Justin Timberlake was arrested in June for DWI, did Leon Silva also think, “This is going to ruin the tour”?

“Man, there was a split second,” he says. “I wasn’t like ‘upset’ about it, because I know the guy now. We’re the same age. He was born like three days after me, and he’s such a cool cat. But I mean, you know, men of a certain age, we understand each other. He had a bad night. You know what I mean? When I woke up that morning my phone was getting blown up by everybody. I looked at my wife. I was like, ‘Well, I think I’m gonna be home for a little while.’ But it’s all good. He made his mistake. He’s paying his price. But he’s a good dude, man. All the love and respect to that cat, for real.”

Silva’s attitude in conversation is as positive as his Instagram captions. In both formats he gives thanks, not only to his parents, but also his wife, Bridget Sarai, who is a performer in her own right, and a Berklee alum as well.

“Standing by a guy like me that long ain’t easy,” he writes about their 20-year relationship in his Instagram caption. “The uncertainty of this career and the jagged-ass path I take and you hold me down.” 

At the end of Silva’s Instagram post, a few inspirational quotes flash upon the screen, including one that says “There is a version of yourself who is proud you didn’t give up.” 

When asked about what this quote means to him, Silva nods quietly, before saying, “Yeah, I’m proud now.”

 Published August 2, 2024

Related Articles