Few new festivals have landed as cleanly at the intersection of music, Bay lifestyle and culture as Sleeping on Gems, debuting Sept. 14 at San Jose’s Discovery Meadow, with Bay Area-born rapper Larry June at the helm.
June—Larry Eugene Hendricks III—has built a reputation on more than just laid-back flows and catchy hooks. The self-made artist’s “organic” ethos has turned him into a cultural figure who blends music, wellness and entrepreneurial savvy into a distinct lifestyle brand. For Bay Area fans, seeing him close out the summer as the first-ever headliner for Sleeping on Gems’ debut event feels like a full-circle moment. Good job, Larry.
Raised in San Francisco’s Bayview–Hunters Point neighborhood, and seasoned by time spent in Atlanta, June’s sound reflects both a West Coast ease and Southern bounce. The rapper started his career out the grassroots way: burning and distributing CDs with his music around Vallejo and across the Bay Area, getting them into Rasputin Music in Berkeley in the early 2000s.
A major-label stint with Warner in 2014 put him on the road with rap peers Post Malone and Smokepurpp, but independence proved to be his true lane. After being released by the label, June saw even more success as an independent artist, going on to release a long string of well-received solo and collaborative projects, including Very Peaceful (2018), Orange Print (2021), Spaceships on the Blade (2022) and The Great Escape (2023), which have earned him a devoted fan base.
Over the last decade, the “Organic” headliner has built a career in his hometown of San Francisco, and across the Bay Area, carving out a niche on his own and with like-minded collaborators like Cardo (Cardo Got Wings), and 2 Chainz and The Alchemist as heard on their latest joint LP, Life is Beautiful—further honing a new subgenre in rap/hiphop that prioritizes laid-back flows, and lyrics that salute financial independence, and toast wellness and self-empowerment. Cuts like “Smoothies in 1991” (2019) and “Private Valet” (2022) offer messages of advice on living smart and stress-free. But June’s “organic” approach extends well beyond his bars.
From his social media presence to his orange-emblazoned merch, June has mastered the art of turning authenticity into influence by championing a philosophy in his music and artistry that emphasizes health and entrepreneurial savvy. In the words of Jay-Z, he’s “not a businessman, he’s a business, man.” Which makes him an ideal anchor for Sleeping on Gems’ debut event—a festival operating with the same ethos: independent, carefully curated and proudly in the know.
Launched first as a music page on Instagram, Sleeping on Gems has amassed 1.4 million followers by spotlighting underground artists, new releases, and exclusive interviews and performances. The move into live events is the brand’s way of taking that curatorial eye off the feed, and onto a stage. Their first-ever festival lineup reads like a carefully plotted playlist full of gems: Pop-R&B starlet Thủy, acclaimed producer Sango, tastemaker DJ Lex, and Montreal wordsmith Lou Phelps, plus Bay-rooted crew Cuffin and DJs Kat Jabba, markmark, RCADE and Zuri Alexa.
The curation is intentional, and the festival’s vibe has a throughline of connectivity—these are all artists who cross scenes, who know how to set a tone, and can easily slip from laid-back to high-energy, without losing the crowd. And it’s the same philosophy that has made Sleeping on Gems a must-follow online: no filler, just gems.
For San Jose, the timing feels right. Discovery Meadow has quietly become one of downtown’s most popular venues for open-air concerts, and Sleeping on Gems’ arrival signals a growing stake in the Bay’s wider music ecosystem. In a region where shows come and go, the festival lands with a particular kind of clarity and feels rooted—in both community, and cultural intent.
The event is widely an extension of June’s brand: music that motivates and moves, the portrayal of a healthy and energizing lifestyle (hello, Specialized bike rides and organic oranges), and connectivity. For longtime fans of June, the festival is an opportunity to see him in a new context—headlining an event that’s beautifully backlit by nature and in a joyous, open outdoor environment that matches his “organic” energy and healthy lifestyle that’s synonymous with the artist after years of cultivation. And for newcomers, it’s an introduction to both his catalog and the Sleeping on Gems brand, one that takes pride in putting you on to gems across the music landscape.
But whether you’re a longtime Larry June listener or simply a fan of the Bay Area hip-hop and rap scene, Sleeping on Gems’ debut festival is a community moment, and maybe the start of something bigger. For June, it’s another chapter in a decade-long climb built on resilience, independence, and his ability to bottle Bay Area cool. For Sleeping on Gems, the festival is a chance to prove they’re more than a music page: they can create real-world moments, not just document them.
Sleeping on Gems takes place 2–9pm on Sept 14 at Discovery Meadow in downtown San Jose. Tickets on eventbrite.com.
