It is a dim night at the Regiis Ova Caviar & Champagne Lounge. Carlmont junior Nathan Tokunaga drove the three-plus hours down to Napa amidst traffic. People are clapping and hooting to the music as Tokunaga jumps straight into a vivid clarinet solo.

Tokunaga started playing his first gig in 8th grade. He was introduced to the gig business by his mentor, American jazz musician Clint Baker. Since then, Tokunaga has played multiple gigs a week and has started his own band, Nathan’s Fearless Five.

Gig culture, specifically regarding music, is the fastest and largest-growing sector of the freelance economy, which includes about 150 million workers in North America and Europe. Those who work in the freelance economy are independent contractors. To Tokunaga, being in the music gig business means becoming a musical chameleon when hired to play for private events, adopting a style to suit the occasion. Tokunaga specializes in jazz and swing from the 1920s-1940s on clarinet and various other woodwind instruments such as the alto and tenor saxophone.

To the jazz world, he is known as an extremely talented musician.

“I have to say, I’ve been doing this for almost fifty years professionally, and I’ve worked with some of the greatest clarinetists in the world. This sixteen-year-old young man, Nathan, is playing at a level I’ve seldom heard—the depth of understanding of New Orleans Jazz—as I’ve heard coming out of that horn of anybody… I’ve been praying for people to play Johnny Dodds like that,” said Steve Pistorius, a pianist from New Orleans who had collaborated with Tokunaga before.

Most of his gigs are residency-based, meaning that he performs on a regular basis at the same venues.

“For some professional gigs, people reach out to me because they know who I am, and the jazz world is small. With the bands I lead, new opportunities can arise because when you’re playing a gig and people from the audience like what they hear, they would want to hire you,” Nathan Tokunaga said.

Tokunaga prepares for gigs by having a large repertoire of tunes and practicing unfamiliar setlist songs. Typically for his gigs, he doesn’t have rehearsals prior or a setlist, as tunes are called on the spot.

“Occasionally I would need to rely on my ear as I’d have to learn a new tune on the spot while it’s being played,” Nathan Tokunaga said.

Like any job, there are issues, such as last-minute cancellations from band members, issues with venues about food and payment, and more. As the bandleader for Nathan’s Fearless Five, Tokunaga has a list of backup musicians in case of last-minute cancellations and always pays his band, whether or not the band is paid by the venue.

“Communication is key in solving those problems, which can take a lot of time and energy,” Nathan Tokunaga said. 

Nathan’s Fearless Five was founded by Tokunaga in October 2021 at Carlmont to raise funds for the New Orleans Musicians Clinic, a non-profit benefiting musicians and culture-bearers without medical insurance. As a result of Hurricane Ida hitting New Orleans, many musicians were left in need, which Tokunaga helped raise funds for.

Since 2021, the band has regularly performed at establishments such as the Old Skool Cafe, a youth-run club that gives training, employment, and a second chance at life for at-risk youths in San Francisco. In addition, Nathan’s Fearless Five has also established residence at the Waterdog Tavern in Belmont to bring live jazz to Belmont and at the Palo Alto Rinconada library.

“The goal of playing at the Palo Alto library is to educate people and children on jazz,” Nathan Tokunaga said. Besides playing at the aforementioned places, Tokunaga also performs for senior living homes and jazz education events.

On average, Tokunaga earns from $125 to $600 per gig, the majority of which he saves for the future. To him, playing gigs is not only a part-time job but is also the best way to become a musician.

“It’s really a privilege to be part of the journey of a musician in the making. I support Nathan in choosing a unique path to music education outside the traditional classroom, a path that is led by true passion, paved with generous support from numerous mentors, and filled with opportunities to learn and grow through real-life experiences,” said Sunny Tokunaga, Nathan Tokunaga’s mother.

To those who are trying to start playing gigs, Nathan Tokunaga recommends having a large repertoire of tunes, a strong work ethic, and being a team player to those trying to start playing music gigs.

“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,” Nathan Tokunaga said.