“Like living inside one of your favorite rap songs”: History of the Bay Day hypes local hip-hop’s diversity

The transition from summer to fall in the Bay Area has typically been the season for celebrating local hip-hop’s legacy. Yet the cancellation of September’s yearly Hiero Day festival in Oakland for the first time in over a decade left fans with a noticeable gap in their calendars. 

Lucky for them, San Francisco emcee, artist, podcast host and lifer Dregs One returns with his second annual History of the Bay Day in the city. A celebration of hip-hop’s core elements, the mini-fest of sorts honors some of the most important names in the local scene, features others on the cutting edge and is doubling in size from its inaugural edition.

“I’m big on experiential events,” Dregs One, who lives in the city’s Lakeview neighborhood, said.  “I want to take people somewhere and leave them with a memory, feeling or a vibe. I want to create a hip-hop Disneyland for adults, putting all of these different elements together in one place so that people really feel like they’re living inside one of their favorite rap songs.” 

History of the Bay Day takes place Sat. Oct. 19 from 2 to 8 p.m., at the Midway gallery complex in the Dogpatch district. Where last year’s function hosted just over 1,000 attendees on the outdoor patio, this year’s event will expand into the entire Midway complex, featuring multiple galleries, a main indoor stage, outdoor patio and rooftop lounge for performances, panels, exhibits and more accommodating up to 2,500 people.

The event’s live performers, all from the Bay Area, include Oakland’s iconic Souls of Mischief crew, celebrating the 30th anniversary of their seminal album, “93 ’til Infinity;” Vallejo’s B-Legit, who was famously in the group the Click, with E-40; as well a rare appearance from East Bay collective Mob Figaz, honoring the memory of revered member the Jacka, who died in 2015. Along with these legacy performers are next-gen rappers in Oakland: leading lady Kamaiyah, DaBoii of Vallejo’s SOB x RBE and local DJs including Mind Motion, Drew Banga and Sean G. 

“We were intentional about curating the lineup to reflect different generations and different styles,” Dregs One says. “DaBoii and B-Legit represent two different generations of Vallejo. Kamaiyah and Dru Down are the same with Oakland. And you might never see Mob Figaz perform again. Heck, I’ve never seen ‘em play.” 

Born Reza Harris, Dregs One grew up entrenched in the graffiti art scene and says he learned the promotions hustle — from community radio to social media — from his teenage years. It’s how he’s still not too proud to drop by Amoeba Records with posters for History of the Bay Day while he’s walking his dog. 

The name of the event comes from Dregs One’s eponymous History of the Bay podcast series of in-depth interviews with figures in Bay Area hip-hop that began in 2022 and now has more than 80 episodes. Many of his interview subjects are appearing at the day-long festival, and he’ll even be recording a live episode with radio station KMEL’s ubiquitous on-air personality, Chuy Gomez.  

“He’s a scholar and a historian, not just a graffiti artist or a rapper,” Souls of Mischief’s Tajai told the Chronicle. “He’s really doing it and not putting it together from Cliff’s Notes. He has the actual people behind the history (of hip-hop in the Bay).”

With the event, Dregs One is not just reflecting on history but also building it and shining a light on what ought not be forgotten. On Saturday, a fundraising effort and Lifetime Achievement award will be given to the Fillmore’s Rappin’ 4-Tay (of “Playaz Club” fame), as he battles myeloma.

“Rappin’ 4-Tay is literally fighting for his life,” Dregs One says. “We want to let him know that we got his back, because this is an industry that doesn’t come with a health plan or a dental plan.”

The event also presents a panel on women in hip-hop hosted by KQED’s Nastia Voynovskaya along with a comprehensive slate of entertainment devoted to hip-hop’s four elements (MCing, DJing, graffiti art and breakdancing). Live graffiti art commissions will be in action by artists Mark Bodē and San Jose’s King 157, along with a skate photo gallery curated by FTC Skateboards. A new dance cypher — hosted by Golden State Warriors hype man Franco Finn and featuring noted strutters, breakers and turfers freestyle dancing — is in the mix now, too. 

“We have our own swagger in the Bay, and dance is a huge part of that. I love that there’s so much to celebrate here,” Finn told the Chronicle. 

A museum of hip-hop artifacts — from MC Hammer’s actual gold baggy pants to Shock G’s Humpty Hump glasses with a fake nose — makes its return. And hip-hop’s unofficial fifth element, cannabis culture, now has a home in the Cloud 415 Rooftop Lounge that even features a munchies cabinet

When you look at History of the Bay Day as a whole, Dregs One’s vision for your favorite rap song coming to life starts to become clear. And ultimately, it shows the power that hip-hop has to bring people together from all walks of life through mutual expression; something the culture in the Bay stands out in especially.  

“We’ve got graffiti writers from San Jose, dancers from all over the Bay, Filipino, Black, Latino, white artists; all nationalities represented. Both men and women too,” Dregs One says. “This is the key to what makes the Bay area so special: The diversity. And that’s why we’re doing this. 

Adrian Spinelli is a freelance writer.

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