Once, they were kids walking the hallways of Oakland School for the Arts. Now they're at the Grammys, publishing bestsellers, and performing at the SF Ballet. Alan Chazaro checks in on five former students who've gone on to do extraordinary things.
“This is the only time in my entire life, I think, where I wrote long and someone was like, ‘Well, could you make it longer?’”
Once, they were kids walking the hallways of Oakland School for the Arts. Now they're at the Grammys, publishing bestsellers, and performing at the SF Ballet. Alan Chazaro checks in on five former students who've gone on to do extraordinary things.
I'll never forget my first months as a public high school teacher in rural Louisiana in 2009. The highs were high, but the hardest days could feel unbearably difficult for a young, inexperienced educator — like trying to balance on a quaking tectonic plate while someone throws gummy bears at you. (That never happened, but I've definitely seen carrots tossed across the room.)
And yet, for every moment that caused me to futilely raise my voice into the void, there were more moments of deep joy, pride, and human connection that few professions can match.
For all of their systemic shortcomings, schools still represent the apex of communal groundwork: a place where adults become ingrained in the lives, matters, and aspirations of young folks, and grow invested in the individual outcomes for every student that walks through the door.
Nowhere did that work feel more fulfilling than my time at Oakland School for the Arts (OSA). During the last three years of my teaching career, which ended in 2019, I taught 9th and 10th grade English and Art History there. OSA spans 6th to 12th grade and offers 10 creative pathways. Every weekday, swarms of creative, quirky kids — dancers, drummers, painters, violinists, photographers, poets, fashion designers — filled the narrow hallways of the school, located above the Fox Theater in uptown Oakland.
It’s one of the few public art schools for teens in the region, and attracts students from all over the Bay Area, with some trekking in from as far as Vallejo. Needless to say, it’s highly competitive, and students have to audition to get in. Famously, OSA has produced game-changing graduates — not limited to generational superstars like 2026 Olympics Gold Medalist Alysa Liu, Kehlani, and Zendaya — and thousands of other students, many who I’ve had the pleasure of keeping in contact with as they’ve gone on to enter college, their careers, and even parenthood.
I reached out to a couple of former OSA students, most of whom I taught for at least one year, to hear about what they’ve gone on to do since we last crossed paths in the classroom. Here’s what they’ve achieved.
A few years before attending UC Berkeley as an art student, well on her way to building a popular Instagram account with over 100,000 followers where she posts her digital artwork (including this viral Squid Game fanart), Isa was a standout 10th grader in my English class with a cool emerging art style. Besides being an engaged critical thinker who could always be counted on to contribute in meaningful ways, Il most remember Isa for designing the cover of my first book, This Is Not a Frank Ocean Cover Album. When the book was accepted for publication, I asked my publisher if one of my students could design the cover. They agreed. I explained my idea to each of my classes and recruited a voluntary group of teenage visual artists for an open-call contest that involved a few weeks of collaboration with an arts teacher. Each student proposed their ideas, drafted copies, and created finalized versions of what my book could look like, and the arts teacher and I used it all as a way to teach the young artists how to work with clients in a professional context. Out of all the dope ideas to emerge from that process, Isa’s design was selected as the winner, and my publisher paid her for her artwork. It’s still my most popular and best-selling book to date, with ongoing comments about the cover (which I always proudly credit Isa for, even when nobody asks). Isa was just 15 years old when she professionally designed the book cover; since then, she has only shone brighter in her art career.
The first time I met Justin, I was substituting and showing a movie to freshmen I'd never met. The group came in rowdy and excited. Justin was different. He greeted me and made an effort to acknowledge me, despite being part of the Popular Kids crowd. I took note of him. For the following three years, Justin would be a major part of my teaching career at OSA. In his junior year, I oversaw a student-mentor club for young men of color on campus, which included Justin and his youngest brother, who was a tiny sixth grader at the time. That’s when I would see another dimension of Justin: as an older sibling and club president who the rest of the school looked up to, despite his quiet and humble nature.
Nowadays, Justin — or Jwalt — is headlining rap shows as a successful Bay Area entertainer. He recently sat in the front row of the Grammys, in which he was considered as a nominee for Best New Artist and Best Rap Album. Coincidentally, another OSA grad, Kehlani won Best R&B Performance and Best R&B Song. As a high school senior in 2020, Jwalt performed at Oracle Arena in his hometown, Oakland, as an opening act for Wu-Tang Clan, and this past year, he recorded the official championship anthem for the Oakland Ballers. He even wrote his own book. SFGATE proclaimed him as being one of Oakland’s next rap stars, a rapper known for his mix of lyricism and honesty. He’s a graduate of New York University’s Institute of Recorded Music. He’s on the radio. He’s a dad. And he still texts and shows love as he always has over the years — with a positive attitude and headstrong sincerity.
Clay is the only person on this list I never formally taught. But OSA is a small family. Many of my former students are friends with Clay, and he was a student in the music studio next door to my classroom. Last year, I ran into him at a Steph Curry-sponsored event in San Francisco before the NBA All-Star Game. Clay was getting ready to perform fa live set with his band and the Vallejo rapper LaRussell, and we saw each other across the crowd. He called out (“Chazaroooo!”) and it was like he had known each other all along from the jump.
In the past year, Clay has exploded as a Bay Area keyboardist and hip-hop producer, with a trademark sound that is equal parts soul music and hyphy. He has credits for songs with other OSA grads like JWalt and Ajai Kasim, but also with rising and established Bay Area rappers, including Seiji Oda, IAMSU!, and so many others. Notably, Clay was on NPR’s Tiny Desk and performed live at the official tailgate party at this year’s Super Bowl in Santa Clara. He also filmed a video of himself making live beats inside Levi’s Stadium during the Super Bowl — maybe the first artist to ever do that? Check out this thumper he produced.
If ever I could say that I taught a legitimate prodigy, Leila is that student. During my first year teaching 10th grade English Honors at OSA, Leilia produced a literal book of poems in the span of a few days (far beyond what I was expecting from anyone for their introduction project). At the time, I was juggling my duties as a creative writing graduate student at the University of San Francisco. Because Leila would always finish her classwork quickly and at an expert level, I began to slip her some readings from my grad courses about poetry and poetic theory. She breezed through the grad-level material and then would work on her own creative writing projects on the side, while other students caught up on their daily assignments. It was no surprise then when Leila would soon become the Oakland Youth Poet Laureate in 2018.
After graduating from Smith College, she published a New York Times bestseller, Nightcrawling, which Oprah selected for her Book Club. Leila doubled down and followed that up by publishing a nationally-acclaimed poetry collection, woke up no light. Oh yeah, she also wrote a second novel, The Girls Who Grew Big and is working on a third. All before turning 25.
One of my favorite varieties of students to teach are those who have siblings — or better yet, are twins. You get to know each student’s quirks, as well as the parents and family —times two. Angela is one of those kids: a sweet, fairly quiet 9th grader in my Art History class who had an R&B-singing twin brother and a very involved mom. I'll occasionally get updates on the twins from Angela's mom; though years have passed, I still enjoy hearing about their lives. Angela, in particular, was in the ballet pathway at OSA — one of my favorites in the school because the program produced students who had incredible posture in their seats and unwavering discipline in academics, unlike those zany theater kids (yes, shots fired). Angela was an exceptional student. She eventually transferred out of the school and joined the San Francisco Ballet School, but not before I had the chance to enjoy her presence as a student for a year. As an adult, Angela is now a dancer in the San Francisco Ballet corps, and has appeared in the Nutcracker, the world premiere of Tamara Rojo’s Raymonda and more.
