.Holiday Aloha, Jake Shimabukuro Appearing at Blue Note Napa

When Jake Shimabukuro talks about the ukulele, he sounds less like a global touring musician and more like someone still smitten with the instrument he first held at age four. “My mom played ukulele,” he recalls. “She sat me down, taught me a few chords, and I just fell in love.”

The small, nylon-strung instrument gave him a feeling kids rarely get so early: mastery. “I got that immediate gratification,” he says. That’s the special nature of the ukulele, even to a four year old, making music easy. “It was something I could grasp quickly, and I stuck with it.”

Raised in Honolulu, Shimabukuro absorbed not only Hawaiian musical traditions but also techniques from guitarists, bassists and pianists—anyone he could watch. “I tried to see how I could take those techniques and apply them to the ukulele,” he says. By high school, he had formed his first band, Pure Heart, gigging in coffee shops and at weddings. A couple of local CDs later, the group had a genuine following.

That momentum carried him across the Pacific. In 2001, he signed a seven-album deal with Sony Music Japan. “I spent a lot of time there from 2001 to 2005,” he notes. “It opened a lot of doors.”

But one door—one he didn’t even know existed at the time—would open wider than all the rest.

In 2006, while performing in New York City, Shimabukuro filmed an interview in Central Park’s Strawberry Fields, a quiet corner dedicated to John Lennon, and played his own arrangement of “While My Guitar Gently Weeps.” Someone—he still has no idea who—ripped the TV footage and uploaded it to a fledgling website called YouTube.

“And then it went viral,” he says, still sounding faintly stunned. “Friends would call me, saying, ‘Hey, someone shared this video of you on the computer.’ I didn’t even know what YouTube was.” The video introduced millions to a style of ukulele playing they had never imagined, and it launched the global touring career Shimabukuro continues now.

“It was like hearing yourself on the radio for the first time,” he recalls. “It opened up a lot of different opportunities that led me to where I am today.”

Shimabukuro’s new holiday record, Tis the Season, grew from a tradition that began four years ago. “We’d been doing this holiday tour, and everyone’s like, ‘Where’s the album?’” he says with a laugh. The trio—Shimabukuro, bassist Jackson Waldhoff and guitarist-vocalist Justin Kawika Young—finally went into the studio last year.

The album features classics they’ve honed on the road: “All I Want for Christmas Is You,” “This Christmas” and a soaring rendition of “O Holy Night” with Young on vocals. It also includes collaborations with friends and heroes including Jimmy Buffett on “Mele Kalikimaka.” “He introduced me to so many people in the industry,” Shimabukuro explains. “I’m super grateful for his friendship and support.”

There’s also an intimate version of John Lennon’s “Happy Xmas (War Is Over)” with Yo-Yo Ma, recorded side-by-side in a New York studio. “To sit next to him while he played… unbelievable,” he says. 

While Shimabukuro’s career benefited from the early days of YouTube, he’s also watching the digital landscape shift again, this time with AI. He recalled hearing an AI-generated track at a venue the night before our conversation. “To my ear, I couldn’t tell it wasn’t a real person singing,” he says. “It scared me a little. I woke up this morning still thinking about it. And it was a great song.”

Shimabukuro plays 100–120 shows a year, but family remains central. “I miss them when I’m gone,” he notes. His sons are in seventh and fifth grade, and he lights up talking about their sports and school life. “I’m loving it,” he adds.

And career-wise? “Just grateful, man,” he says. “It’s been an awesome year.”

Jake Shimabukuro’s Holidays in Hawai’i, featuring Jackson Waldhoff and Justin Kawika Young, plays five shows on Nov. 28, 29 and 30 at Blue Note Napa, 1030 Main St., Napa. Purchase tickets online at bit.ly/4pdXCW1.