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Nathan Tokunaga has had a busy year. In 2025, the Peninsula-raised jazz musician helped lead Stanford Jazz Workshop’s Miles Ahead Big Band in the Essentially Ellington competition at New York’s Lincoln Center, worked with a 50-piece orchestra and pianist Charles Chen to record Chen’s new album, and most recently, received a Young Arts Award, which recognizes “excellence in visual, literary, and performing arts.”
He also graduated from Belmont’s Carlmont High School this spring, and is now living in New York City, studying music at The New School.
Tokunaga, a clarinetist and saxophonist, has been playing music since fourth grade.
Before he left for college, he performed regularly at area venues. Although his focus has long been jazz, he also honed his classical chops as principal clarinet with the Peninsula Youth Orchestra.
In recent years, local audiences may have heard him playing with Nathan’s Fearless Five, the band he founded that was made up of fellow students, as well as soloing with other local jazz groups. Nathan’s Fearless Five frequently played gigs at the Old Skool Cafe in San Francisco, and on the Peninsula, at Palo Alto’s Rinconada Library, and other venues like The Tavern in Belmont.
As the Rinconada Library’s first musicians-in-residence, the band performed monthly there over the last two and half years, up until June 2025, when its members graduated high school and began heading off to college. But with the bandmates back in town for the holidays, Nathan’s Fearless Five is reuniting for a special winter concert Dec. 21 at the library.Â
Bay Area audiences can also catch Tokunaga performing the Duke Ellington Nutcracker Dec. 20 in Healdsburg with the Marcus Shelby Orchestra. Later in the month, he’ll be flying out to the Lindy Focus big band and swing festival in Asheville, North Carolina.
As a college freshman, he’s already working with and learning from some big names in jazz.
“Here at the New School, the classes I’ve been taking are just insane. I’ve taken a class from Reggie Workman, who was John Coltrane’s bass player for a long time, and hearing him just talk about this direct connection, (it was) just like passing on the torch to everyone, and having this sense of direct knowledge is very awesome. I also met, got a bit close with (bassist) Gene Perla, who directed one of my ensembles — he played with Stan Getz,” Tokunaga said in an interview with this publication.
Tokunaga specializes in traditional, or classic, jazz from the 1920s, ’30s and ’40s.
“it’s very melodic, and it’s dance music, something that’s not really found in a lot of music in general, after that period. I mean, there’s just different variations, but especially in jazz, I feel like that was the era where it was really like America’s pop music,” Tokunaga said of what drew him to the genre.
He was struck by “how musicians of that era turned popular songs from Broadway shows and movies into these really swinging recordings and used jazz to interpret those.”
Now in New York, he’s playing at well-known clubs in addition to pursuing his studies.
“New York, it’s been super wonderful. It’s such a totally different vibe. It’s super intense. I think my sleep schedule from going out has been totally messed up,” Tokunaga said with a laugh. “But I played at places like Smalls, Birdland, and then some other places like Swing 46 which is in Times Square, and also the Ear Inn, which is a huge spot for this kind of jazz I specialize in.”
His first gig, about a week after arriving was at legendary jazz club Birdland, where he’s played several times since.
Traditional jazz may not be commonly found in the playlists of most teens. But Tokunaga had an ear for it, said his mentor, Peninsula musician Clint Baker, who said he “quickly realized that he was going to be quite a talent” and described him as having “perfect pitch.”
“He was like a sponge, but he also has the musical gift to really take it over the top. One of the things he proved to me early on, is that if I gave him a recording of a classic jazz musician like, say, Sidney Bechet or Louis Armstrong, he would figure it out. He would figure it out by ear, so he can figure out all of the subtleties, all of the nuance by ear.”
Traditional jazz also isn’t typically taught much in schools, noted Nathan’s mother, Sunny Tokunaga, which is why she approached Baker at a South Bay Traditional Jazz Society meeting about mentoring Nathan.
“Clint was Nathan’s very first mentor on what jazz actually is, which was tremendously beneficial,” she said.
Baker is a multi-instrumentalist who plays traditional jazz. He’s a longtime bandleader and also hosts a regular show on Peninsula jazz radio station KCSM.
Tokunaga’s regular Peninsula gigs also included the Cafe Borrone All Stars, a longtime jazz gig run by Baker out of Menlo Park’s Cafe Borrone. (In fact, the All Stars will mark their 35th anniversary on Jan. 23.)
He noted that Tokunaga meshed well with the All Stars musicians, despite them being older.
“Nathan just fit in perfectly with them. He was just great, great fit. He was able to really work well with everybody,” Baker recalled.
When Tokunaga told him he wanted to form his own band, Baker was also in a good position to advise him, as he also started his first band when he was a young teen.
“His band’s been very successful, and they’ve lasted a long time, and the thing that I’m most proud of, he was able to cultivate an environment in his band, like my band, where people want to be in the band, and they stick with him. His original core musicians are still working with him, and now that they’ve gone off to school, well, it’s great that they’re still all interested in playing,” Baker said.
Tokunaga said that for their return to the Rinconada Library, Nathan’s Fearless Five will play a lot of holiday tunes, jazz standards and even a nursery rhyme for the youngest audience members.
He expressed a hope of making jazz feel accessible to listeners.
“I just hope people can when they come to the Rinconada Library, they just see us. We’re just playing music for the people and not for ourselves. And I hope people really resonate with that and see that and enjoy the music most of all,” Tokunaga said.
Nathan’s Fearless Five will perform Dec. 21, 3-5 p.m., at the Rinconada Library, 1213 Newell Road, Palo Alto. Admission is free. paloalto.bibliocommons.com.
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