PAY YOUR FRIEND$ with Cipha Sounds
PAY YOUR FRIEND$ is hosted by Cipha Sounds, aka Mr. Very Famous in New York, Mr. Name Droppa, Mr. Don’t Get Gassed. This show is about supporting the people who’ve supported you, reconnecting with old friends, and making new ones along the way. Every episode asks a simple question. How have you helped a friend today? From hip-hop to comedy to life lessons, Pay Your Friends delivers serious things the silly way. Expect real conversations, laughs, and stories you didn’t know you needed. Come for a good time. Stay for a long time. And don’t forget to pay y...
40. DJing for Dave Chappelle, Busta & LL Cool J at MSG | PYF$ with Cipha Sounds
Cipha Sounds breaks down the weekend he spent on stage at Madison Square Garden with Dave Chappelle, with Rocky and Janice in the room.
He gets into the controversy that blew up the day after the show and why the outrage machine misses the point, the comedians using the moment for clicks, the difference between satire and a street-corner speech, and why he went home to pizza and Family Guy instead of the afterparty.
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39. The Dating Truth Nobody Wants to Hear with Dante Nero | PYF$ with Cipha Sounds
Cipha Sounds brings Dante Nero back in to break down his whole philosophy on honesty, attraction, and keeping your word.
Starting from boxer Julio Cesar Chavez’s claim that he never really cheated, Dante lays out his ACE principle (authenticity, credibility, empathy) and the idea that once someone catches you in a lie, nothing you say after carries weight. He gets into why giving a woman things doesn’t build attraction, the difference between a trick and a pimp, and a long story about one client whose marriage came down to a Cinnabon at the airport.
38. The Time Julio Diaz Ruined a Mexican Wedding ft. Kevin Dombrowski | PYF$ with Cipha Sounds
Cipha Sounds has comedians Julio Diaz and Kevin Dombrowski in the studio, and Julio comes prepared with bullet points so he actually gets a word in this time.
The three of them get into how little Julio knows outside of New York (sports, geography, which countries are actually countries), road stories from opening for Ralph Barbosa, why cruise shows are the best thing going right now, and the usual run of Ciph name-drops.
Catch Julio Diaz at JulioDiazComedy.com and the Comedy Cellar, and Kevin Dombrowski at KevinDombrowski.com. Cipha’s Don’t Get Gassed reun...
37. Any Party Diddy Showed Up To Became a Diddy Party | Jon Laster & Alex English | PYF$ with Cipha Sounds
Comedians Jon Laster and Alex English join Cipha Sounds for a long one that covers a lot of ground.
Ciph gets into the Jamaican shower posse and Dudus, how the latest prison news connects back to him, and why he refuses to let people rewrite who Diddy was to an entire generation. The three of them trade stories from the come-up, back when comedy clubs were still trying to sell bottle service at stand-up shows, and get into the hood-to-alt-circuit jump, the To Catch a Predator documentary, and why the people who raised the block never get...
36. Keith Robinson on Old-Head Wisdom vs. the Algorithm | Reggie Conquest & Matt Richards | PYF$ with Cipha Sounds
Keith Robinson has mentored half the comics working today. He pulls up with Reggie Conquest and Matt Richards to tell Cipha Sounds what the next generation is getting wrong. The group gets into why everything now bends to the algorithm, how marketing and slang keep chasing the youngest people in the room, and why that’s the wrong instinct. Keith makes the case that the kids should be learning from the people who came before them, not setting the terms. They talk about the death of the gatekeeper and what it actually did, the difference between guarding the gate an...
35. Seasick Steve & Matt Richards on Music, Art & the Blues | PYF$ with Cipha Sounds
Cipha Sounds hangs out with blues musician Seasick Steve and Matt Richards for a warm, loose conversation that turns into something special.
Seasick Steve talks real music, the blues, and life in Norway, then picks up one guitar and plays a song that stops the whole room and gets Ciph emotional. Matt Richards makes live art right there in the studio. Along the way they get into Dave Chappelle's cornfield jam sessions, the Biggie breakfast debate, McDonald's fries, and the time Ciph told Bootsy Collins how funk really works.
34. Why Hip-Hop Hits Harder Than Any Genre Worldwide | Statik Selektah, Julio Diaz & Destroy | PYF$ with Cipha Sounds
Cipha Sounds hangs out with producer Statik Selektah, comedian Julio Diaz, and SiriusXM host Destroy for a loose, wide-ranging conversation.
They get into Statik's new album and its stacked features, why real hip-hop travels further than any other genre (from New York to a club full of Japanese fans in Fukuoka), reggaeton and bachata's roots in hip-hop, Irish and Puerto Rican heritage, Star Wars versus Star Trek, and plenty of unfiltered New York stories along the way.
Catch Statik Selektah's new album out November 13th on Mass Appeal, Julio Diaz on YouTube (Ralph Barbosa Presents...
33. Maino's Advice for Surviving Your First Day in Jail | PYF$ with Cipha Sounds
Cipha Sounds sits down with his brother Maino — Brooklyn rapper and co-host of the hit podcast Let's Talk About It — to talk about a friendship that goes back more than 15 years.
Maino shares the best advice for surviving your first day in jail, plus how he and Ciph really met (fresh out of a 10-year bid), his come-up to hit records like "Hi Hater," why elevation and reinvention are the real flex, and the pushback against rappers doing podcasts. It's two old friends talking real, unfiltered, and funny.
Catch Maino live at the American Dream on O...
32. The 9/11 Comedy Benefit at MSG: Behind the Scenes | Brendan Sagalow & Andre D Thompson | PYF$ with Cipha Sounds
Cipha Sounds hangs out with comedians Brendan Sagalow — hip-hop head and host of Sagdaddy the Pod — and Andre D. Thompson, recorded on 9/11.
Ciph takes them behind the scenes of the night before: DJing the NYC Still Rising 9/11 benefit at Madison Square Garden for John Stewart and Dave Chappelle, with Machine Gun Kelly, Pete Davidson, Bill Burr, Nikki Glaser and more. He breaks down the art of reading a comedy crowd on a somber night, secretly running the room from the DJ booth, and picking the right songs when you can't play half your set. From there it goes...
32. NyQuil, a Facial, and a Podcast | Talia Romina | PYF$ with Cipha Sounds
Comedian Talia Romina shows up to the studio with a face full of facial oil after double-dosing NyQuil the night before, squeezing in a workout, and running straight from a 90-minute facial she thought was 50 minutes. Cipha gets the full story. Plus: the war on entitled cyclists in New York, whether being friendly to a waitress counts as flirting, the ultrasound tech who hits on Talia every six months during her liver checkup, and Cipha's case that he never gets hit on — which Talia spends the rest of the episode dismantling.
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32. Fired for a Luigi Mangione Joke | Rahul Pandya | PYF$ with Cipha Sounds
Comedian Rahul Pandya lasted three days at a healthcare tech startup before getting fired over a Luigi Mangione joke his boss dug up on his social media. Cipha gets the full story. Plus: Cipha reveals he spent 20 minutes charming a woman at a Hollywood Hills party before finding out it was Charli XCX, Tom Cruise tracked him down in a green room to compliment his DJ set, the origin story behind Drake's "Shut Up Janice," why Jay-Z's post-retirement catalog doesn't hold up, and the eternal first date debate — drinks or dinner?
31. P-Lo on Repping the Bay, E-40 & Out the Box | P-Lo & Salma Zaky | PYF$ with Cipha Sounds
Cipha Sounds sits down with Bay Area rapper and producer P-Lo — in New York promoting his new album Out the Box — with comedian Salma Zaky in the room.
They get into what it really means to rep the Bay, the region's hip-hop culture and "same squad" spirit, coming up with HBK and Kehlani, how tech changed the Bay the way gentrification changed New York, and the time Dave Chappelle brought P-Lo out at a Super Bowl show.
Out the Box is out now, featuring E-40.
30. Dave Chappelle at Lauryn Hill Festival & Coming Out of Retirement | PYF$ with Cipha Sounds
Cipha Sounds and Rocky Powell break down what actually went down backstage at the Lauryn Hill festival — the Fugees' 30th anniversary reunion with Wyclef Jean, Erykah Badu, Dave Chappelle, Giggs, and more.
Ciph tells the full story: flying to London for Dave's shows, thinking he was hosting, ending up playing dominoes in the crowd — and then getting rushed on stage with zero DJ equipment when Lauryn's setup ran long, tearing the whole thing down off a headphone jack while Dave hyped him up as a hip-hop legend. Plus the viral moment when they cut the sound, halal pepp...
29. People Just Do Nothing's Seapa & Hugo on Why the US Sleeps on UK Music | PYF$ with Cipha Sounds
Cipha Sounds links up in London with Seepa and Hugo — the guys behind pirate radio crew Kurupt FM from the BBC series People Just Do Nothing — for a deep dive into UK music and why it connects to New York more than Americans realize.
They break down the whole family tree — jungle, garage, grime, drum & bass, funky house, drill — and trace it all back to Jamaica and the Jamaica-London-New York-Toronto pipeline. Plus how Afrobeats crossed over, why UK actors keep taking the hood roles in American movies, London vs. New York on slang, food, and air...
27. Smif-N-Wessun on Why New York Feels Like It Used To | PYF$ with Cipha Sounds
Cipha Sounds hangs out with Brooklyn legends Smif-N-Wessun — Tek-N-Steele, aka the Cocoa Brovaz — for a real conversation about old New York, the culture, and staying true after 30 years in the game. They get into the Decepticons and growing up between Brownsville and Bed-Stuy, Sunday rituals and the legendary Tunnel nightclub, how gentrification changed Brooklyn, why the Knicks run brought that old New York energy roaring back, and what it really means to say "I am hip-hop." Plus stoop sets, outfit architecture, and always showing up for your friends. Catch Smif-N-Wessun at City Winery (Pier 17) August 31st, and at the Smif...
Derek Gaines on Being Cul-de-Sac Black | PYF$ with Cipha Sounds
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
26. Rick Ross on Hustlin', Going Broke to Get Rich & Set in Stone | PYF$ with Cipha Sounds
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.
25. Funny Makes You Better Looking | Rob Haze | PYF$ with Cipha Sounds
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...
24. Why This Is the Best Summer of Your Life | Ian Lara | PYF$ with Cipha Sounds
Comedian Ian Lara joins Cipha Sounds and Rocky Powell for the first LIVE episode of PAY YOUR FRIEND$. They get into the Knicks championship run, why old-school NYC energy is back, jazz clubs, dead nightlife, and why Summer 2026 might be the best one yet — plus Ian's confession that he hates all animals.
23. How Caribbean Culture Built London & NYC Hip-Hop | DJ Snips | PYF$ with Cipha Sounds
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.
22. SQUASHING BEEF WITH NATHAN & REGGIE | PYF$
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."
21. Jay Z, Nas, Griselda & Pooh Sheisty 101 | Salma Zaky | PYF$ with Cipha Sounds
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.
Cipha quizzes Salma on everything from Jay-Z's name origins to the four pillars of hip-hop, and somehow she keeps landing answers through pure energy and Brooklyn osmosis. Along the way they break down Nas lyrics line by line, decode rapper nicknames, and get into the current state of the culture. In this episode: • Jay-Z's "Reasonable Doubt" 30th anniversary at Yankee Stadium + the "Blueprint" 25th • Why he's called Hov, and th...
20. What Makes You a Real New Yorker? | Simeon Goodson & Lenny Marcus | PYF$ with Cipha Sounds
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...
Ice-T Drops Gems on Street Wisdom, Body Count & Raising Kids | CIPHA SOUNDS PYF$ | Ep 19
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. Ice-T opens up about growing up as an orphan in New Jersey, being shipped to LA, navigating gang-heavy neighborhoods without joining a gang, and how love — not fear — is what actually protects you. He breaks down why emotional decisions are dangerous, how to read a room before things go sideways, and the real reason you should...
Bad Dates, Hecklers & Dating Red Flags | Dante Nero & Aldana | CIPHA SOUNDS PYF$ EP 18
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 ow...
LIVE TOKYO TRIP Q&A | PAY YOUR FRIEND$ | CIPHA SOUNDS | EP 17
Cipha Sounds is back from Japan and he’s got stories. On this episode of Pay Your Friends, Ciph and Rocky talk about Tokyo nightlife, Japanese hospitality, 20,000-step shopping days, viral Family Mart fried chicken pancakes, One Oak Tokyo, after-hours food runs, Japanese BBQ, Don Quijote, sneaker shopping, and why Tokyo somehow makes everybody more polite. Ciph explains why “Pay Your Friends” is more than a podcast, Rocky learns what BAPE stands for, and the crew goes fully live for the first time.
BRITTANY BRAVE | PYF$ | EP 16
In this episode of "Pay Your Friends," Cipha Sounds sits down with the incredibly funny Miami-born, NYC-based comedian Britney Brave. They dive into a hilarious and unfiltered "Straight Shooters" segment, tackling everything from wild conspiracy theories and "passport bros" to the brutal realities of modern dating and situationships.
MEMPHIS BLEEK | CIPHA SOUNDS PYF$ | EP 15
In this video, Memphis Bleek joins the discussion to share insights on loyalty, fatherhood, and his legendary career in the music industry. They delve into the concept of "paying your friends" through support and respect, and Bleek recounts wild stories from his time on the road with Jay-Z and meeting global icons.
DOITALL DUPRE KELLY | CIPHA SOUNDS PYF$ | EP 14
On this episode of Pay Your Friends, host CIPHA SOUNDS welcomes legendary rapper and Newark West Ward Councilman Dupre "DoItAll" Kelly. The conversation explores Dupre's roots in the "bricks" of Newark, his early days in hip-hop with Redman as his DJ, and his transition into politics. They discuss the importance of community leadership, affordable housing, and the unique cultural pride of New Jersey.
BIRTHDAY SHOW RECAP W/ MAX GLAZER | CIPHA SOUNDS PYF$ | EP 13
In this episode of Pay Your Friends, the host discusses his recent sold-out birthday celebration at the Gramercy Theatre, which combined legendary New York comedy with classic hip-hop. Joined by his longtime friend and fellow DJ, Max Glazer, the two provide an "oral history" of the star-studded event that featured a lineup including Dave Chappelle, Funkmaster Flex, Mo Amer, and Busta Rhymes. The discussion reflects on the host's 15-year journey into professional comedy and the deep-seated loyalty shared among industry veterans.
01:52 - The host introduces his guest and "best friend," renowned DJ Max Glazer. 04:13 - Discussing the goal of s...SALMA ZAKY 2.0 with ROCKY POWELL | CIPHA SOUNDS PYF$ | EP 12
Welcome back to another episode of Pay Your Friends! On today's show, we have our good friend and comedian Salma Zaky back for an amazing comeback—though she might just call it a defense of her reputation. We're also joined by the one and only Rocky Powell, aka Rocky Balboa. Following the uproar in the hip-hop community from Salma's first appearance, we’re diving headfirst into the comments that went "ham" after she revealed she didn't know what R\&B stands for. We'll be addressing everything from "caucacity" to cinder block threats. To settle the score, we’re putting everyo...
SEAN AND GIDEON @side.questz | PYF$ | EP 11
Cipha Sounds welcomes Sean Patton and Gideon (aka Side Quest) to the "Pay Your Friends" podcast for a lively discussion on cultural differences, the perils of being "online," and navigating relationships. The group explores the surprising historical and cultural links between Ireland and Jamaica, before diving into a candid conversation about Jamaican social norms and common misconceptions. From sharing stories about high-profile encounters with Dave Chappelle to debating the elusive "ick" factor in dating, the episode blends humor with personal anecdotes. The show wraps up with a mission to find a long-lost acquaintance in Jamaica and some expert travel...
ZAR THE STAR & DOMINICAN DREW | PYF$ | EP 10
Join host Cipha Sounds and guest Zar the Star as they dive into the complex history and internal conflicts of the legendary New York hip-hop group, Dipset. Zar the Star offers a unique perspective from Toronto as they explore potential ways to reconcile the group's long-standing beef.
RAY DANIELS | PYF$ | EP 9
In this episode of Pay Your Friends, host Cipha Sounds sits down with music executive and media personality Ray Daniels for an in-depth conversation on success, industry regrets, and the importance of intentionality. Ray shares personal stories about breaking major records like Rick Ross’s "Hustlin'," the evolution of hip-hop podcasting, and the mental shift required to move from a "hustler" to a true entrepreneur. The two friends discuss the value of mentorship, the reality of being a "giver" in a "taker" industry, and why establishing clear goals is the ultimate key to reaching the next level of success. 00:00...
SUNNY ANDERSON & JOURDAIN FISHER | PYF$ with Cipha Sounds | EP 8
Join the crew on "Pay Your Friends" for a deep dive into the world of food, career wins, and high-stakes scenarios. This episode features Food Network star Sunny Anderson and the "Gangster Chef" himself, Jourdain Fisher. From Sunny’s major career update with The Drew Barrymore Show to Jourdain's unique kitchen lingo and a "Chopped"-style jailhouse cooking challenge, this conversation is packed with laughs and incredible stories.
GORILLA NEMS & CONEY ISLAND FRIENDS | PYF$ with Cipha Sounds | EP 7
Cipha Sounds (aka Mr. Very Famous) tries to build a “real New York” travel guide… and it instantly derails into a chaotic, unfiltered hang with Gorilla Nems and the FYL crew.
What starts as a wholesome itinerary turns into a wild tour through Coney Island, pigeon coops on abandoned buildings, hood economics, and the evolving definition of “goons.” Along the way they debate microplastics, old-school vs new-school NYC, borough pride, and why Brooklyn will always be its own universe.
ZAHID DEWJI & EVA EVANS | PYF$ with Cipha Sounds | EP 6
Cipha Sounds (aka Mr. Very Famous) kicks off Pay Your Friends… then it immediately turns into a masterclass on dating Jamaican women, Clarks + skinny jeans, “one man to the ting,” and why asking for $500 shouldn’t cause a financial crisis.
Guest comedian Eva Evans breaks down the real rules: money, generosity, boundaries, and why she avoids Jamaican men (too much “gal,” too much stress). Plus comedian Zahid Dewji tries to learn how to “walk up game” a Jamaican girl, discovers dubplates, and accidentally invents the most perfect catchphrase of 2026.
“I’M USING SCRAM A LOT.”
KARDINAL OFFISHALL | PYF$ with Cipha Sounds | EP 5
Cipha sits down with Kardinal Offishall and talked a lot of Hip Hop, and their Top 5 Dead rappers. It's a great episode. Pay your friends.
JUANYTO & SAANIYA ABBAS | PAY YOUR FRIEND$ with Cipha Sounds | EP 4
Cipha Sounds links up with longtime radio vet DJ Juanyto and comedian Saaniya Abbas for a chaotic, hilarious, and surprisingly thoughtful hang that zigzags from Hot 97 history and a “Drop a Gem” name dispute to Dubai nightlife, deli-order etiquette, and the difference between being “important” and being “nice,” mixing nonstop laughs with real perspective on culture, identity, internet fame, and the wild world of unsolicited DMs.
ANTI-ICE GIRLIE | PAY YOUR FRIEND$ with Cipha Sounds | EP 3
Cipha Sounds welcomes attorney and community organizer Robin Richardson alongside comedian Liam Dalton for a sharp, hilarious, and urgent conversation on ICE, immigration enforcement, and grassroots resistance. From neighborhood patrols to legal realities, they break down what’s happening on the ground and how everyday New Yorkers can protect their communities.