Dregs One, San Francisco rapper and preeminent local hip-hop historian, might just be the hardest-working guy in the city.
He was everywhere at Saturday’s second annual History of the Bay Day, a festival he’s masterminded. There he was onstage, interviewing radio DJ legend Chuy Gomez; there he was backstage, shaking hands with everyone in the green room, no matter how famous; there he was, impromptu freestyling to keep the crowd entertained (and stall for time) as we waited for Oakland superstar Kamaiyah’s delayed performance.
The History of the Bay Day is a labor of love. Dregs has billed the event as a “a hip-hop Disneyland for adults,” giving shine to the Bay Area’s deeply influential, criminally underrated hip-hop culture. With the long-running Hiero Day festival put on ice this year due to financial woes, Dregs One’s event, held this year at the Midway, remains one of the few big Bay Area love-letters to the genre, and the folks here who keep it alive.
At various moments, the day-long affair was a mini music festival, a tribute to stars both new and old, and a block party for the Bay’s biggest hip-hop heads. Moderated conversations early in the day — one with Gomez, and another with KQED editor Nastia Voynovskaya, spotlighting women in the industry — had the air of folks chopping it up. The chats had a similar vibe to Dregs’ ongoing History of the Bay podcast, the inspiration for the event, which many of the day’s guests had appeared on previously.
The crowd, too, had an easy, casual flow. Everywhere you looked, there were folks dapping and introducing so-and-sos to each other. It felt like a kickback of the highest order.
Spread out across the entirety of the Midway — an upgrade from last year’s event, which was confined to the venue’s outdoor space — every inch of space had something to do. There were booths selling Frisco merch, tooth jewelry, boutique psilocybin products, and limited-edition vinyls; DJs inside and out spinning local classics loud enough to feel the low end in your chest; and all kinds of food and drinks, including a Mitchell’s Ice Cream cart. There was also plenty of room left for folks to roll and light up blunts, which many attendees did with abandon.
Throughout the day, the focus was on giving living legends their due. Shortly before the performances started, seminal Fillmore rapper Rappin’ 4-Tay, one of the Bay’s early hitmakers and a contributor to 2-Pac’s All Eyez on Me, received a Lifetime Achievement Award. The tribute doubled as a fundraiser; he is battling multiple myeloma, a cancer affecting the bone marrow, and posters and table signs around the event had QR codes directing attendees to his GoFundMe page.
Of course, the main attractions were the live acts, which were brief and rollicking, a Bay Area greatest hits compilation brought to life.
Vallejo OG B-Legit speed-ran through his suite of slaps, including his verse on early E-40 hit “Captain Save a Hoe,” a song whose chorus has been interpolated in rap hits across three decades. Kamaiyah’s set, despite a 45-minute delay and a valiant attempt by Dregs to entertain an antsy audience, was still a treat. (Never mind her pausing the show near the beginning, as security escorted someone out of the crowd for starting some shit.) “How Does it Feel” and “Fuck It Up” were classics the first time I heard them, and still hit today.
Not to be outdone, Vallejo’s DaBoii ripped through both his solo work and his work with SOB x RBE before bringing on Kiwi, an angel-voiced friend he’d met during a recent stint in prison, for a sincerely wonderful collaboration called “Child of the Ghetto.” And, of course, there was legendary Oakland group Souls of Mischief, putting on “‘93 to Infinity” and promising to “represent this real hip-hop from now until infinity.”
Midway through the sets, Dregs came on stage again. “I think we gon’ have to come back next year,” he croaked to wild applause, having lost most of his voice somewhere along the way. “I think the Bay Area needs a hip-hop festival that's all about Bay Area hip-hop.”
If anyone can make it happen through sheer force of will, my money's on Dregs.
