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.
Lock in with DJ Pup Dawg every single day on the iHeartRadio app, and make sure you’re following the movement on all socials @djpupdawg!

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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.
Listen to DJ Pup Dawg everyday 3-9p "Drive Home With Pup" on Boston's Number 1 For Hip Hop & The Best Throwbacks, also on San Diego's Jam'n 95.7 from 3-8p. Follow Pup for all the BTS on all his socials at @djPupDawg

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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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The legendary Michael Bivins of BBD called with DJ Pup Dawg about his massive homecoming for the New Edition Legacy Tour at the TD Garden. In this exclusive first part, Biv opens up about his Orchard Park roots, the philosophy of respect that has kept him grounded through decades of fame, and the incredible story of how a chance encounter led to him discovering Boyz II Men. From the magic of playing the Garden to the star-studded lineup featuring Toni Braxton, Biv explains why there is truly no place like home.
Biv also explains why New Edition keeps their show tight and consistent, even when performing for the hometown crowd at the Garden. The conversation takes a personal turn as Biv and DJ Pup Dawg share "full circle" stories from the past—including Pup’s days as Johnny Gill’s banker and his run in with Bell at the gym before Pup was in radio. Plus, Biv details the Boston Neighborhood Heroes Awards honoring local basketball legends and gives a final shout-out to the fans ahead of Sunday's massive Legacy Tour stop at the TD Garden with Boyz II Men and Toni Braxton.
Listen in for a masterclass in legacy and find out how you can witness music history this Sunday!

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Get ready for some serious West Coast vibes with a side of New England flavor! In this episode of Party With Pup, the legendary DJ Pup Dawg sits down with Compton’s own Compton AV. Known for his infectious energy and undeniable hustle, AV dives deep into what it truly means to stay independent in an ever-changing industry.

The two discuss the massive success of his recent hit "YAYA" (and the star-studded remix featuring Snoop Dogg). From his early days in the streets of Compton to becoming a staple in the West Coast rap scene, AV drops gems for any aspiring artist looking to build a career on their own terms.

But it wouldn't be a DJ Pup Dawg interview without a little local hazing! We put Compton AV to the ultimate test in the "Pronounce These New England Cities" game. Watch (or listen) as the West Coast powerhouse tries to navigate the linguistic minefield of towns like Worcester, Gloucester, and Billerica. It’s a hilarious moment that shows why Pup is one of the best in the business at bridging the gap between his Boston roots and the global hip-hop scene.

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Every Thursday, DJ Pup Dawg connects with Asha, the Roxbury Liaison, to discuss the latest news and initiatives across Boston. In this episode, they are joined by Renato Castelo, Director of the Office of Participatory Budgeting, to discuss a major opportunity for residents to decide how city money is spent.

The Power of Your Vote

Renato explains the concept of Participatory Budgeting, a democratic process where Boston residents directly decide how to allocate a portion of the city’s budget. While a youth-focused version has existed in Boston for over a decade, the city recently expanded the program to include everyone.

Key highlights from this episode include:

• The $2.2 Million Decision: Residents are currently voting to narrow down 13 community-proposed ideas into the top five projects to be funded.

• Proposed Projects: Ideas on the ballot include increasing access to fresh food, youth financial literacy workshops, and installing benches at bus stops.

• Social & Racial Justice: Renato explains how the program is designed to support the residents who need it most, including formerly incarcerated youth.

• How to Get Involved: Voting is open through February 15th and is available in multiple languages at boston.gov/participate.

City Updates with Asha

Asha also shares vital resources for the community, including how to use the Boston 311 app to report neighborhood issues like potholes or housing concerns. Additionally, she discusses the city's homeless census, where city employees head out late at night to connect unhoused individuals with warm shelter and essential resources.

Don't let others decide where your tax dollars go—listen in to find out how you can have a direct say in Boston’s future!

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In this deep-dive interview, Adekunle Gold sits down with DJ Pup Dawg to explore the evolution of his sound and the philosophy behind his artistry. From debating the best musical eras between the 70s and 90s to explaining why constant change and "breaking" what works is essential for creative growth, Adekunle shares his personal secrets to building a "timeless" legacy. The conversation touches on his eclectic inspirations—ranging from his Nigerian roots to the influence of Maroon 5—and reveals the unexpected impact of rap music on his latest project. Beyond his own discography, he provides a masterclass on the rich diversity of African music, highlighting the unique rhythms of Fuji, Amapiano, Kizomba, and Soukous to show that the continent’s sound is far more expansive than just Afrobeats.

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In this engaging interview, DJ Pup Dawg sits down with Grammy-winning songwriter and artist Joelle James as she returns to her "second home," Boston. The conversation dives deep into Joelle’s impressive career, from her early YouTube discovery by Chris Brown in her Berklee dorm to writing culture-shifting hits for major artists. Joelle shares the heartfelt philosophy behind her music, her dedication to spotlighting local Boston talent, and the inspiration behind her upcoming EP, I-Scream Scoop Two, which features the lead single "Love Over Everything." From hilarious stories about singing the National Anthem at the NBA Finals to a fun game of trying to pronounce tricky Massachusetts town names like "Haverhill" and "Leicester," this episode is packed with gems about resilience, manifestation, and her mission to give back to the city that "made" her.

Watch the full interview here: https://www.youtube.com/watch?v=kb1UiraEwjA

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