Pimp Daddy Podcast

Send us Fan Mail This week Brad Rickert and Sheri Ciprane are joined by comedian Rebecca Kaplan for a wild ride through the weird corners of comedy, culture, and modern life. The gang investigates why Pimp Daddy somehow has a suspiciously strong German fanbase, debates the sexuality stereotypes surrounding Jewish women, and tries to figure out what WWE actually stands for. Along the way they dive...

Send us Fan Mail Episode 81 of the Pimp Daddy Podcast features comedian and rapper Fluke Human joining Sheri Ciprane and Brad Rickert for a wild conversation that bounces between comedy, music, and questionable life choices. We dive into Fluke’s experiences working for TaskRabbit, the differences between writing stand-up comedy and writing rap lyrics, and what makes battle rapping such a unique ar...

Send us Fan Mail Brad Rickert and Sheri Ciprane are back with another chaotic episode of the Pimp Daddy Podcast. This week the duo talks Met Gala insanity, the roast of Kevin Hart, Funny AF, No Doubt performing at the Sphere, rising gas prices, filing unemployment in New York, and a massive blackjack win. They also get into Knicks playoff hype, dating coworkers, Chet Hanks going country, how much...

Send us Fan Mail This week on the Pimp Daddy Podcast, Brad Rickert and Sheri Ciprane sit down with NYC comedian and content creator Nate Stein to talk internet fame, stand-up comedy, and the weird corners of American culture. The crew debates golf vs bowling, rich white people vs poor white people, cigar culture, and why terrible strip clubs somehow beat the expensive ones every time. Nate breaks...

Send us Fan Mail This week on Pimp Daddy, Brad Rickert and Sheri Ciprane are back with a wild solo episode covering everything from celebrity chaos to road comedy horror stories. We get into Tiger Woods’ latest drama, Kanye’s return concert at SoFi, our Mount Rushmore of SNL women cast members, and the controversy around Jaden Ivey. We also break down a brutal Connecticut road gig where Sheri got...

Send us Fan Mail This week on Pimp Daddy, Brad Rickert and Sheri Ciprane sit down with NYC comic and Roast Battle NYC producer Dan Wickes for a comedy-heavy episode that goes deep on stand-up, roasting, and the chaos around the scene.  Dan talks about dating with Tourette’s, what it takes to run Roast Battle NYC, and which cities have the best roast battle comics in the world. The conversation als...

Send us Fan Mail Comedian Seth Payne pulls up and it goes everywhere. We get into the Bad Bunny halftime hype, why the “rich vs poor” divide feels more real than ever, and what dating outside your culture actually looks like—especially when Latinas are involved. From there it spirals into Buffalo road gigs, questionable party scenes, and the kind of people you meet when you stay out too late. We a...

Send us Fan Mail This week on Pimp Daddy, Brad Rickert and Sheri Ciprane dive straight into the headlines and the hot takes. We break down the passing of Catherine O’Hara and what it says about artists working well into their 80s. Are creatives built differently? Then we tackle the Epstein files and the uncomfortable reality of conspiracy theorists sometimes being right. No fluff — just real talk....

Send us Fan Mail Brad and Sheri go solo and get into the Epstein files, debates around Michael Jackson and Kanye West, and a NYC comedy club shut down over sexual assault allegations. They also talk Black History Month, the Winter Olympics, and why collectibles might be beating the stock market right now. Comedy, controversy, and real talk from the NYC scene. New episodes weekly.

Send us Fan Mail On this episode of the Pimp Daddy Podcast, hosts Brad Rickert and Sheri Ciprane welcome back returning guests Asif Lakhani and Kayla Engeman for a wide-ranging, funny, and brutally honest conversation. The crew dives into NFL talk, how dreams reflect real-life anxiety and ambition, and what the Year of the Horse might mean for motivation, discipline, and momentum in 2026. They bre...

Send us Fan Mail In Episode 72 of Pimp Daddy, Brad and Sheri jump into a wild mix of the biggest cultural and news moments right now: the controversial Minnesota ICE raids and the tragic shooting of Renée Good by a federal immigration agent that’s sparking protests and political firestorms. Then they shift gears to the chaotic Somalian daycare situation, comparing how childcare and community issue...

Send us Fan Mail On this solo episode of the Pimp Daddy Podcast, Brad and Sheri bounce through everything from naming babies and raising stepchildren to surviving NYC tourist traps and the brutal world of roast battles and rap battles. Sheri breaks down her unexpected trip to the ER, we talk about Ozempic, parenting in 2025, and why anime kids might be the new theater kids. The conversation spiral...

Send us Fan Mail Brad and Sheri run a no-guest episode and cover way too many topics: therapy breakthroughs, NYC stories, streaming drama, sports betting, and whatever else came up. A loose conversation with actual laughs. NYC comedy podcast • pop culture • comedians talking

Send us Fan Mail In this week’s episode of Pimp Daddy, hosts Brad Rickert and Sheri Ciprane kick things off by recapping their wild trip to Philly—including Sheri’s unexpected run-in with an ex-girlfriend at a bonfire in Delaware. We get into everything from which rappers might secretly be gay, to how to survive a brutal hangover, to the way people used to be proudly and casually homophobic withou...

Send us Fan Mail Welcome to the 6-Sided Circus, the very first live episode of the Pimp Daddy Podcast, coming straight from Chicago! In this unique show, every roll of the dice determines the next performance—stand-up sets, improv games, wild audience interactions, and more—making for a comedy experience that’s completely unpredictable. Featuring a stacked lineup of Chicago’s funniest comics, this...

Send us Fan Mail In this episode of Pimp Daddy with Brad Rickert & Sheri Ciprane, we dive into a wild week — from the New York City election results and Zohran Mamdani’s big win to our Chicago trip where we stayed with friends, hit the road, and sold out our live comedy show. Then things get presidential when we welcome our guest — President Joe Biden.  Joe talks about Donald Trump’s presidenc...

Send us Fan Mail We finally have a new studio… and zero self-control Brad Rickert and Sheri Ciprane talk Halloween parties, sober dancing, Rudy Giuliani, and intimacy — because apparently we can’t stay on one topic.  They also dive into the cultural phenomenon that is Bad Bunny and what his Super Bowl appearance means for American culture Subscribe for weekly chaos, comedy, and questionable opinio...

Send us Fan Mail This week on Pimp Daddy, hosts Brad Rickert and Sheri Ciprane sit down with comedians Ian Fidance and Amanda Vasco for a wild, hilarious ride through topics that probably shouldn’t be in the same sentence. Ian talks about Tony Hawk teaching him to skate, how bad he is at flirting, and growing up as Sheri’s cousin. Amanda opens up about losing her virginity, peeing standing up with...

Send us Fan Mail In this week’s episode of the Pimp Daddy podcast, hosts Brad Rickert and Sheri Ciprane dive headfirst into the biggest pop culture and political stories making headlines. We break down Charlie Kirk’s latest hot takes, the state of free speech in America, and why Jimmy Kimmel is back in the spotlight. Plus, we get into Cardi B’s surprise pregnancy announcement and what it means for...

Send us Fan Mail In this new episode of the Pimp Daddy Podcast, Brad and Sheri break down the week’s biggest cultural and political chaos with their signature mix of comedy and sharp commentary. Topics include: *The shocking possibility of gay marriage being revoked and what it means for LGBTQ+ rights in America. *Donald Trump sending troops into D.C. and Chicago and the fallout that could bring....

Send us Fan Mail On this episode of the Pimp Daddy Comedy Podcast, Brad and Sheri dive into Colbert’s cancellation and Trump’s influence on late-night TV, the madness of Brain Rot Summer 2025, Rosie O’Donnell being right, and what’s heating up in the WNBA. Then we’re joined by Rebecca Kaplan — New York City stand-up comic, comedy producer, and podcaster — for a hilarious deep-dive into musicals, k...

Send us Fan Mail 🎙️ New Episode of Pimp Daddy Podcast | Happy Gilmore 2 Review, Marc Maron vs Theo Von Drama, Nelk Boys & the President of Israel, Pamela Anderson + Liam Neeson, & Comedian Kyle Wayne In this episode of the Pimp Daddy Podcast, Brad and Sheri dive into:  • 🎬 A full review of Happy Gilmore 2 and why Adam Sandler’s comeback has comedy fans buzzing.  • 🎤 The latest comic-on-c...

Send us Fan Mail This week, Sheri and Brad kick things off with a wild first half — breaking down the news of Hulk Hogan and Ozzy Osbourne’s deaths, Sydney Sweeney’s nostalgic American Eagle ad, and the strange but adorable world of Labubu toys. In the second half, we sit down with Atlanta-born and New York based comedian Asif Lakhani to talk religion, travel, and what it’s like being Muslim while...

Send us Fan Mail On this wild episode of Pimp Daddy, Brad and Sheri chop it up with Jack Sullivan, a hilariously bold gay comic from NYC (by way of Catholic school and the DC suburbs). Jack spills tea on: ☕️ Meeting Jennifer Lopez in a gym locker room 💀 His real-life connection to Murder Inc. 🌈 Coming out after college 💥 Bottom baiting (yes, it’s exactly what it sounds like) 🎭 Will Smith, Kim...

Send us Fan Mail This week on Pimp Daddy, Brad and Sheri sit down with Brooklyn-born comedian Kyle Lewis! Kyle’s been a fixture in the NYC comedy scene for years, running his long-standing stand-up show Character Select at The Stand. The three dive deep into nerd culture—Comic Con hype, growing up geeky in the city, and the surprisingly large Venn diagram between anime fans and foot fetishists. Th...