Sway spent the better part of the 2000s at MTV, where he was best-known as the host of Total Request Live. In 2011, as satellite radio began to take off, he migrated to Sirius XM, where he now hosts Sway in the Morning on Eminem's Shade45 channel. (Sirius recently acquired the streaming service Pandora, where Sway Fest will take place.)

No matter where he broadcasts from, it's clear Sway's heart is in Oakland.

"With Sirius XM, and now Pandora included, these are tech companies and they do pretty well. And now, they’re building their roots in Oakland. So I think it's important that we bring things to Oakland, and feed that cultural well of Oakland, that community," says Sway. "And make sure that the folks who are actually from Oakland are able to benefit from these resources, that they're recognized and that they're able to enjoy the profits that will be coming in the near future."

Along with a live talk show and musical performances at Sway Fest, Sway will interview activists from Kongo SQ West Kinship Society, which will collect donations of sweaters and socks for those in need, and the Choose College Educational Foundation, a group that offers scholarships to local youth.

Championing Bay Area Artists

G-Eazy, who freestyled on Sway in the Morning before scoring 10 entries on the Billboard Hot 100, is one of those artists Sway has championed from the early days of his career, when he was still selling CDs out of his backpack.

"I don’t think it was luck," Sway says of G-Eazy's rise. "I think it was a lot of hard work, mixed with talent, mixed with more hard work."

And Mistah F.A.B. is someone Sway has known since his Wake Up Show days, when he was introduced to Sway as an out-of-this-world freestyle rapper. In the years that followed, F.A.B. became one of the defining voices of the Bay Area's hyphy movement, co-wrote a hit single for Chris Brown, pioneered many philanthropic projects and opened a streetwear boutique-meets-community hub, Dope Era.

"He's always in the heart of the community," Sway says with admiration. "Whether he's giving away backpacks, or creating safe spaces for kids to come to and be creative at Dope Era, he consistently makes music."

Deeper Than Rap

These days, Sway in the Morning and the online platform Sway's Universe are more than just hip-hop. Recently, Sway interviewed UC Berkeley ecologist Mary E. Power on climate change, and Sway's Universe correspondent Mike Muse often reports on political issues like the rise of white nationalism.

That sums up Sway's view of his show—and hip-hop as a medium—as a place where people can hold dialogue, even if they disagree. (Of Kanye West's transformation into an avowed Trump supporter, he diplomatically says, "I think he's well within his rights to have the political views that he has.")

"We wheel out a lot of folks to speak from different perspectives and different sides of the fence, and sometimes folks get upset," he says. "And I say, nah, it's good that we all hear each other's voices."

Sway Fest takes place on Oct. 18, 9am-1pm, on the block outside of Pandora Headquarters (on Franklin Street, between 21st and 22nd Streets in Oakland), and streams on Sirius XM channel 45. Details here.