Cipha Sounds sits down with his longtime friend, comedian Derek Gaines, to talk about his new special Goodlum and being "cul-de-sac black" — a good hoodlum from the suburbs who loves hood culture but grew up on the quiet streets.

They get into Derek's road from cleaning toll booths on the Garden State Parkway to the Comedy Cellar, the time Bradley Cooper pulled them into his movie outside the club, why kids are dancing and buying CDs again, and plenty more.

Check out Derek's new special, Goodlum, on Tubi

Cipha Sounds sits down with Rick Ross to celebrate 20 years of Port of Miami and the new album Set in Stone. They get into how "Hustlin'" broke on Hot 97, why you've got to go broke a few times to become a real boss, old Miami, and Ciph's ongoing campaign to get Ross to franchise him a Wingstop.

Set in Stone is out now.

Comedian Rob Haze (Atlanta-raised, LA-based) pulls up to the studio and Ciph breaks out the Trump umbrella he jacked 15 years before anybody thought Trump could be president.

They get into riders and the mythology of one-time Air Force Ones, why funny makes you better looking, Jamaican patois and dancehall's problematic hits, the masked white nationalists on the DC bus, doxing, Mamdani's first months, the Knicks' championship afterglow, Alvarado's Brooklyn energy, and the time Ciph sang a song he didn't understand to a waitress in Charlotte.

Serious things, the silly way. How have you helped a friend today?

Comedian Ian Lara joins Cipha Sounds and Rocky Powell for the first LIVE episode of PAY YOUR FRIEND$. They get into the Knicks championship run, why old-school NYC energy is back, jazz clubs, dead nightlife, and why Summer 2026 might be the best one yet — plus Ian's confession that he hates all animals.

Cipha Sounds sits down with London-born, NYC-based DJ and producer Snips (aka Todd Worsnip — founder of Barbershop Records and Livin' Proof) for a deep dive into UK music and how it really connects to New York.

Ciph has been championing UK and Caribbean sounds since 1999, and the two of them get into why it never quite breaks through in the States — plus the Jamaica-to-London-to-Brooklyn pipeline that built so much of what we call hip-hop. With Rocky in the room taking guesses, it goes everywhere.

On this episode of the "Pay Your Friends" show, host Cipha Sounds brings old and new friends together for an energetic discussion on the many faces of anger. Comedians Nathan Macintosh and Reggie join Cipha to recount their past "on-sight" beef from 2014 and debate everything from the current state of hip-hop and R&B to the frustrations of airline food. Whether they are analyzing viral plane confrontations or discussing why some people just can't get a birthday invite, the trio dives deep into what makes them "crash out."

PAY YOUR FRIEND$ is back and comedian Salma Zaky is back for her third appearance — this time to get a full hip-hop education whether she wants it or not.

What does it really mean to be FROM New York City? Cipha Sounds, Simeon Goodson, and Lenny Marcus go deep on one of the most hotly debated questions in the city — and it's more than just an address.

The conversation kicks off with the Peter Rosenberg and Noreaga hot 97 morning show drama, where Noreaga said it felt good hearing New York voices on New York radio — and Rosenberg, born in Maryland, took it personally. The crew breaks down why "living here for 20 years" doesn't automatically make you a New Yorker, and what actually does: riding the subway as a kid, knowing what a New York police lock is, having certain spots close down on you.

They also get into gentrification and how neighborhoods like Williamsburg, East New York, and Coney Island have transformed — and who's really being displaced at each wave. Plus: New York sports allegiances, the racial and cultural mix that makes the city unlike anywhere else, teaching kids street smarts, guardian angels on the subway, and some wild transit stories you won't forget.

Ice-T sits down with Cipha Sounds and Dante Nero on Pay Your Friend$ for one of the realest conversations you'll hear all year. What started as a fun visit turned into a full-blown survival guide — packed with hard-earned wisdom, street philosophy, and genuine laughs.

Aldana joins Cipha and the crew, and she did NOT come empty-handed — she brought some of the wildest first date horror stories you've ever heard. From a drunk date who wouldn't stop heckling at a comedy show and made a comment about his own mom that left the whole room stunned, to a guy she met on TikTok who somehow topped that disaster, Aldana holds nothing back.

Dante drops his ACE framework — Authenticity, Credibility, and Empathy — and breaks down exactly why so many guys talk themselves right out of a good situation. Rocky shares her own chaotic dating experience with a con artist (yes, they later made a TikTok page about him), and Cipha somehow manages to derail every conversation with Happy Days spin-off trivia and bathroom confessions that nobody asked for.

This episode has everything: Knicks playoff game drama, mood stabilizers, Balkan geography lessons, the wingman debate, and a 26-year-old finance bro who sent the most unhinged text after one date. The PAY YOUR FRIEND$ cookout is officially open.