South Carolina’s own Trap Dickey sits down with DJ Pup Dawg to celebrate his hit record "Down South" breaking into the top 30. The two dive deep into the track’s iconic sample—originally from the Lafayette Afro Rock Band—and how Dickey’s upbringing on 90s R&B and old soul shaped his unique sound. Dickey also opens up about the importance of stepping out of his comfort zone to reach a national audience while keeping the unwavering support of his hometown fans. With a new album dropping this March, Trap Dickey is proving he's ready to take the rap game to a whole new level.
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Wale pulls up on DJ Pup Dawg to break down his latest album, Everything Is A Lot. In this candid session, they talk about the four-year process behind the project, the "fake toxic" energy of modern dating, and why Wale thinks listening to your own music is "psychotic." From Grammy red carpet moments to the power of nostalgia and industry validation, Wale keeps it 100 on his legacy and the drive that’s taking him back to the Grammys next year.
In the second part of this deep dive, Wale and DJ Pup Dawg get into the specific vibes of the new album, Everything Is A Lot, including the standout Leon Thomas collab "Watching Us". The conversation shifts to Wale’s evolution in the industry—from the MMG era to his current status—and why he’s finally prioritizing his own creative peace over label politics. Wale also shows love to his Boston fanbase, looking ahead to his headlining show at the House of Blues this June and explaining why the city’s energy always brings out a different side of his performance. It’s a raw, unfiltered look at one of the game's most consistent lyricists as he prepares to take this new chapter on the road.
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Asha and Pedro Cruz joined DJ Pup Dawg to break down the massive community energy hitting Boston this weekend! Pedro, the Director of the Office of Youth Engagement, gives the lowdown on the 3rd Mayor’s Youth Summit happening this Saturday, February 21, from 3–6 PM at Artists for Humanity. It’s a completely free event featuring live performances—from rappers and dancers to a brass band and violinists—plus free food, fresh merch, and a keynote from the Mayor.

The crew also discusses the start of Ramadan, with Asha sharing where listeners can find info on local Iftars to break their fast and connect with the community. Whether you're looking for youth empowerment or spiritual connection, the city is active this weekend!

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