Navigating the Music Gig Scene: A Glimpse Behind the Curtains with Jazz Prodigy Nathan Tokunaga

by Madonna

In the intimate setting of Regiis Ova Caviar & Champagne Lounge, Carlmont junior Nathan Tokunaga recently showcased his musical prowess, driving three-plus hours to Napa to deliver a captivating clarinet solo. This talented jazz musician, known for his dynamic performances, shared insights into the thriving world of music gigs.

Tokunaga’s journey into the gig economy began in 8th grade, mentored by acclaimed jazz musician Clint Baker. Since then, he has immersed himself in the freelance music scene, leading to the creation of his own band, Nathan’s Fearless Five.


The gig culture, especially in the music domain, stands as the fastest-growing sector within the expansive freelance economy, encompassing around 150 million workers in North America and Europe. Those participating in this sector, including Tokunaga, function as independent contractors, adapting their musical styles to suit diverse occasions when hired for private events.


Specializing in jazz and swing from the 1920s-1940s, Tokunaga, a master of the clarinet and various woodwind instruments, has gained recognition as an exceptionally talented musician within the jazz community.


Renowned New Orleans pianist Steve Pistorius expressed his admiration for Tokunaga’s skills, stating, “This sixteen-year-old young man, Nathan, is playing at a level I’ve seldom heard—the depth of understanding of New Orleans Jazz.”

Most of Tokunaga’s gigs are residency-based, involving regular performances at the same venues. He highlighted the networking aspect within the small jazz community, emphasizing how new opportunities often arise from audience members expressing interest in his performances.

Tokunaga’s preparation for gigs involves maintaining a vast repertoire of tunes and practicing unfamiliar songs. Notably, he rarely conducts rehearsals or follows a setlist, as tunes are called on the spot, requiring him to rely on his musical intuition and adaptability.

Despite the joys of performing, Tokunaga acknowledges the challenges inherent in the gig industry, ranging from last-minute cancellations to venue-related issues. As the bandleader for Nathan’s Fearless Five, he maintains a list of backup musicians and ensures his band members are compensated, regardless of venue payment.

Established in October 2021, Nathan’s Fearless Five originated at Carlmont to support the New Orleans Musicians Clinic, benefiting musicians without medical insurance. The band has since performed at various venues, including the Old Skool Cafe in San Francisco, the Waterdog Tavern in Belmont, and the Palo Alto Rinconada library.

Beyond the stage, Tokunaga actively engages in community outreach, performing for senior living homes and participating in jazz education events. His dedication has not only enriched the cultural landscape but also raised funds for those affected by Hurricane Ida in New Orleans.

Reflecting on his gig earnings, which range from $125 to $600 per performance, Tokunaga views playing gigs as more than a part-time job; it’s a vital step in his journey to becoming a seasoned musician. His mother, Sunny Tokunaga, commends his unique approach to music education, led by passion and supported by mentors.

For aspiring musicians entering the gig scene, Tokunaga advises cultivating a vast repertoire, maintaining a strong work ethic, and emphasizing teamwork. “You only have to be good enough to be hired, but no matter how good you are, if people can’t work with you, they won’t hire you,” he wisely concludes.


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