This Fall, DJ Pup Dawg will have called Boston home for 25 years. At iHeartMedia’s JAM’N 94.5, he runs the station, mixes the records, mentors the next wave, and still goes out to the clubs to check the room. At this point, that’s not a job description. That’s a calling.
When I asked DJ Pup Dawg what still excites him about radio and Hip Hop after all these years, it’s still the music, and specifically helping to platform new artists.
“I still love planting the seed and watching it grow,” he said. “New artists come along, you build a relationship, you believe in their music — and then it takes off. And you’re like, okay, cool. I still know music.”
Pup Dawg has spent a quarter century building one of the most respected Hip Hop brands in the Northeast. In that time, he has evolved from a DJ who never wanted to touch a mic into one of Boston’s most recognized on-air voices.
He didn’t plan it that way. But he also didn’t fight it.
From the Decks to the Director’s Chair
Pup Dawg started with one goal: be a DJ.
“I never wanted to crack the mic, I never wanted to be a jock” he said. “I just wanted to DJ and was on the private side — showing people what I wanted to show, but not more… I always just wanted to show my art as a DJ.”
Over time, the role shifted. People told him he sounded good on air. He started talking more between mixes. Then came production, running the board, learning every corner of the operation before the PD title ever became a possibility.
“I knew I always wanted to run radio, but I didn’t think it was going to come to the capacity of actually running the whole thing,” he said. “Now I’m the Program Director, Music Director, Assistant Music Director, On-Air Mixer, National Show… (these days) whoever is working in radio, you have to do more than five jobs.”
That depth of experience matters. When something goes wrong at the station, Pup Dawg can usually fix it before engineering gets the call. That’s not an accident — it’s the result of learning everything from the bottom up.
Trust the DJ — Or Don’t. Here’s the Difference.
The conversation around DJs and radio programmers has always carried some friction. Pup Dawg lives in both worlds now, and he understands both sides.
I asked Pup if he felt like programmers today understand the value of on-air mix shows. “If the programmer is a DJ, yes — they get it,” he said. And laughed adding quickly, “if they’re not, no.”
He’s not throwing anyone under the bus. His point is more nuanced. Club DJs know which records move rooms. But a record that lights up a club at midnight doesn’t always translate to drivetime. Programmers who don’t DJ don’t fully trust the DJ’s instincts. And some DJs don’t understand programming well enough to make the case.
The real differentiator, in his view, is batting average. Build it over time, and listeners trust you. Play J. Cole before J. Cole was J. Cole. I was listening to Pup Dawg recently and heard him shout out emerging New York artist Maithili Raelle while she was headed to the JAM’N studio with record exec Kevin “Inca” Valentini. When those artists do make it, the credibility compounds.
“The trust comes from your listeners,” he said. “And it takes a while.”
As for what separates a DJ on the radio from a Spotify algorithm? Pup Dawg doesn’t hesitate.
“Element of surprise. That’s always going to be the key.”
Radio Still Matters to Music. Period.
There’s a version of this industry conversation where radio is always on defense. Pup Dawg isn’t interested in playing that game.
“I think radio will never die,” he said. “A playlist is a radio station. All those things were created off of what we did in radio.”
He points out something most people don’t consider: streaming playlists repeat songs. They weight recurrents just like radio does. They move songs in and out on a weekly cycle. The architecture is identical — radio just invented it first.
His take on whether radio can still break records is unambiguous. Once a song lands on radio, it’s official. He compared it to the NBA: “We’re the top of the top. Once it gets onto radio, it’s like — okay, it’s here. It’s real.”
Regional Identity Still Exists
We talked about regional hits, especially in Hip Hop and both agreed that’s why regional programming still matters. Boston isn’t San Diego. The Caribbean influence that fills JAMN’s mix show doesn’t play the same on the West Coast, and that’s exactly the point.
“You’re not playing Serani outside of here,” he said. “And that’s what makes Boston so special.”
He gets listeners from Phoenix tuning in specifically for the reggae and Afrobeats flavor mixed in with Hip Hop. That’s not an accident — it’s a deliberate programming identity that only works when someone in the chair actually cares about the culture.
“Being here in Boston, when people come visit from say the West Coast, they’re like ‘oh you’re playing different music’ and we’re not playing that much different, but it’s because of those couple of records, it switches up the whole station,” he said. “I think that’s very important. You don’t want everyone to sound the same.”
Giving Back to the Culture That Built Him
Earlier this year, Pup Dawg produced his first concert — a benefit show for Jamaican hurricane victims, with Shaggy headlining. For someone who has DJed fundraisers for 15 years, stepping into the producer role was a deliberate next level.
“My career and that culture and that music is why I am where I am,” he said. “Jamaica is like the third home to me. They needed the help, and I had the connections.”
He’s not stopping there. His next focus is music programs in Boston schools. Not the well-funded ones, but the ones with broken piano keys and dusty instruments nobody replaced. He wants to change that.
The goal he’s building toward? A benefit concert at Boston’s largest arena, the TD Garden. He’s giving himself five years.
Pup Dawg also mentors a handful of young people interested in radio. “Someone made the time for me,” he said, reflecting on his own path. “That can’t be an excuse why you can’t excite some of these kids who want to do media and radio.”
Gut Over Data. Always.
If you want to understand Pup Dawg’s philosophy on programming in one line, here it is: 65% gut, 35% data.
Pup still goes out. He watches DJs. He reads the room at clubs and concerts — sometimes 15,000 people deep. That’s his data. Not just hooks tested in a vacuum.
“I’d rather use that kind of data than someone sitting behind something listening to a bunch of hooks and going, yes or no,” he said.
He’s not anti-research. He’s anti-over-reliance. The balance matters. Push it too far in either direction and you lose the thing that makes radio feel alive.
And that feeling — the surprise, the community, the DJ who shouts out a listener by name and knows what’s happening in their hometown — is what Spotify can’t replicate. That’s what Pup Dawg is protecting. That’s what he’s building toward, one record, one mentor, one benefit show at a time.
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Bethany Kent is a Music Radio Editor for Barrett Media. She spent nearly 20 years bringing radio to life on stages, across the airwaves, and through unforgettable listener experiences. Her career spans local markets including Providence, Philadelphia, and New York City, most recently serving as National Director of Music Initiatives for Audacy. From producing major live events like HOT 97’s Summer Jam to leading strategic national marketing initiatives, she has built a career at the intersection of music, media, and culture. She can be reached at bethany@barrettmedia.com.
