After 100 Episodes, ‘History of the Bay’ Expands Its Horizons

When Dregs One finally met Too Short face-to-face this past February, during NBA All-Star weekend in San Francisco, the two weren’t exactly strangers. Short, of course, is a Bay Area rap icon, now 22 albums deep in the game — and he’d definitely noticed Dregs’ work to tell the stories of the region’s hip-hop producers, graffiti artists and rap pioneers on his History of the Bay podcast.

It was only fitting, then, that Too Short be the guest on the landmark 100th episode of History of the Bay — an appearance that Dregs tells KQED has been a longtime goal. Short’s been “very supportive since the beginning, in terms of commenting, sharing and engaging on social media,” allowing for what’s usually an hour- or hour-and-a-half-long conversation on the podcast to last for more than two hours.

It’s the culmination of a long road for History of the Bay, which began in early 2022 as short TikToks. Onscreen, Dregs would summarize entire careers or scenes in in 60 seconds or less. (The first two? Graffiti spot Psycho City and Tupac Shakur.) Some blew up with as many as half a million views, and six months later, the podcast was born — a way to stretch out beyond TikTok’s time limitations and hear from the artists themselves.

Now, Dregs is expanding yet again. Episode No. 101 will feature actor Danny Glover, and Dregs wants to host more actors, activists, journalists and musicians of different genres on History of the Bay.

“I’d actually be interested in like, regular people. School teachers!” Dregs says. “I want to get this podcast to where it doesn’t really matter who I have on, the audience is strong enough to trust me to know that whatever story gets told will be interesting.”

It’s also been a time of literal expansion for the podcast, which recently moved to the office of record label EMPIRE, whose sponsorship comes with a small production team, including videographer Trevor Potter and production manager Jazmin Ontiveros. Having the support of EMPIRE’s CEO Ghazi Shami “really means a lot to me,” Dregs says. “This culture is important to him.”

And while reporting on said culture can involve egos, beef and grudges, Dregs has enough street knowledge to sidestep them (“it’s really served me well by going out of my way to not be messy,” he says). He intersperses interviews of rappers like Philthy Rich, Messy Marv and LaRussell with graphic designers like Shemp or personal injury billboard queen Anh Phoong. And, for October, he’s already planning a return of the History of the Bay live event at the Midway in San Francisco.

As for what the podcast might look like another 100 episodes from now, Dregs says he just wants to continue pushing Bay Area culture to an international audience, “so they learn about the Bay and start appreciating it more.”

‘History of the Bay’ drops new episodes weekly, and can be found on podcast platforms and YouTube.