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Emmy Award—winning producer, actor, and comedian Larry Wilmore is back on the air, hosting a podcast where he weighs in on the issues of the week and interviews guests in the worlds of politics, entertainment, culture, sports, and beyond.
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You're the Boss

Red Hat Media, LLC | Larry Roberts

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The phrase "You're the Boss!" is a mantra for anyone who's ever had to face their own fears, struggles and even failures. It's time to take a deep dive into overcoming limiting beliefs, identifying where our past can shape us rather than define us and build a rock solid lifestyle and business filled with passion and purposeful leadership! Hosted by Larry Roberts, each episode of You’re the Boss will bring you experience, proven techniques and mind shifts that you can leverage to develop the ...
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Larry is joined by writer and media executive Mark Whitaker to discuss his newest book ‘The Afterlife of Malcolm X: An Outcast Turned Icon’s Enduring Impact on America’. They begin their conversation by talking about what inspired Mark to write the book and detailing Malcolm X’s Shakespearean life journey from harrowing childhood to celebrated civi…
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Larry starts off a special listener mailbag episode by sharing some of his biggest concerns with Donald Trump’s second term so far and his administration’s attack on government agencies and the Constitution. Next, he talks about the brand-new Pope Leo XIV and the role of religion in modern society (22:23). After the break, Larry discusses the futur…
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Larry is joined by professor of law at the University of Michigan Law School and co-host of the podcast ‘Strict Scrutiny’, Leah Litman, to discuss her forthcoming book ‘Lawless: How the Supreme Court Runs on Conservative Grievance, Fringe Theories, and Bad Vibes’, publishing on May 13th. They begin their conversation by talking about how the politi…
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Larry is joined by billionaire entrepreneur and ‘Shark Tank’ costar Daniel Lubetzky, and they begin their conversation by analyzing the importance of independent thought in today’s political climate. They then focus on the objectives of the Builders Movement and Daniel's efforts to curb political extremism and heal divisions within the business com…
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Larry is joined by political journalist Tara Palmeri, writer of ‘The Red Letter’ Substack and host of The Ringer podcast ‘Somebody’s Gotta Win’, to discuss all of the latest buzz shaking up Washington D.C. They begin their conversation by analyzing the possible political repercussions of Trump’s new tariffs. This leads into a talk about the viabili…
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Larry is joined by Axios Senior Political Reporter Alex Isenstadt to talk about his new book ‘Revenge: The Inside Story of Trump’s Return to Power’. They begin their conversation by discussing Alex’s approach to writing the book and the environment surrounding Trump when he decided to run for president a second time. They then analyze the personali…
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Larry is joined by actress Krys Marshall to talk about the Season 2 release of her Hulu show ‘Paradise’. They begin their conversation by examining Marshall’s upbringing and the many factors that inspired her to become an actor. This leads to a conversation about the mental, interpersonal, and familial hurdles Krys overcame to reach her personal go…
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Larry is joined by filmmakers George and Teddy Kunhardt to discuss their newest documentary ‘Becoming Katharine Graham’, currently streaming on Amazon Prime Video. They begin their conversation by talking about what inspired them to start the project and shining a light on the male-dominated world Katharine lived in when she was running the Washing…
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Larry is joined by writer and cultural critic Thomas Chatterton Williams to discuss his latest essay for The Atlantic, "How the Woke Right Replaced the Woke Left". They begin by shining a light on the political left’s weak hold on the cultural landscape, and breaking down the definition, history, and downfall of "woke" ideology. Next, they take a l…
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Larry is joined by actor and comedian Roy Wood Jr. and they begin their conversation by acknowledging Black History Month. Roy then breaks down his new CNN show ‘Have I Got News for You’ and opines on whether or not comedic "bubbles" will last under the new Trump administration (5:41). They then pivot to his recently released stand-up special on Hu…
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Larry is joined by journalist and MSNBC political analyst Juanita Tolliver to discuss her new book, ‘A More Perfect Party: The Night Shirley Chisholm and Diahann Carroll Reshaped Politics’. They begin their conversation by talking about what inspired Tolliver to write about the legendary political fundraiser and shining a light on the many influent…
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Larry is joined by CNN Anchor and Chief Legal Analyst Laura Coates, and they begin their conversation by talking about Laura’s stylistic approach to the interviews she conducts on her show ‘Laura Coates Live’. They then break down the defamation case between ABC News and Donald Trump and discuss the reasons why there is currently a general mistrust…
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Larry weighs in on the L.A. fires. He’s then joined by writer and Academy Award-winning filmmaker RaMell Ross to discuss his newest movie ‘Nickel Boys ’(8:33). They begin their conversation by talking about how the project came together, RaMell's experimental inspirations, and the screenwriting process with co-writer Joslyn Barnes. Next, they dive …
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Larry is joined by Emmy Award-winning writer and producer Alan Zweibel to discuss his experiences working on ‘Saturday Night Live’ during its first few years on the air. Alan begins the conversation by sharing his feelings about the 50th anniversary of ‘SNL’ and detailing the anatomy of a good joke. Larry and Alan then talk about Lorne Michaels’s o…
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Larry is joined by technology journalist Emily Chang to talk about her Bloomberg Originals limited series ‘Posthuman’, and her podcast ‘The Circuit’, which features interviews with influential figures in the tech industry. They begin their conversation by discussing the inspiration for ‘Posthuman’, which delves into humanity’s connection to artific…
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Larry is joined by writer and historian Timothy Shenk to discuss his newest book, ‘Left Adrift: What Happened to Liberal Politics’. They begin their conversation by talking about why they think the Democrats failed with their messaging in the 2024 election and what the rise of Trumpism means about American culture today. Next, Shenk shares the hist…
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Larry weighs in on the results of the presidential election and the future of the Democratic Party. He’s then joined by political commentator and host of the new iHeartRadio podcast ‘Off the Cupp’, S.E. Cupp, and they begin their conversation by sharing their reactions to Donald Trump winning the presidential election (18:01). They then examine the…
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Larry is joined by comedian Samantha Bee and chief content officer at The Daily Beast, Joanna Coles, to discuss their latest venture ‘The Daily Beast Podcast’. They begin their conversation by shining a light on how they started the podcast and the interesting way Joanna connects creative luminaries in her industry. They then quickly pivot to an ex…
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Larry is joined by journalist and writer Craig Unger to discuss his newest book ‘Den of Spies: Reagan, Carter, and the Secret History of the Treason That Stole the White House’, which investigates the secret collusion between the U.S. government and Iran and how it affected the 1980 presidential election. They begin the pod by diving into the histo…
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Larry weighs in on his recent tour, the newest season of ‘Reasonable Doubt’, and the upcoming presidential election. He’s then joined by writer, statistician, and founder of the site FiveThirtyEight Nate Silver to discuss his newest book ‘On the Edge: The Art of Risking Everything’ (15:27). They begin their conversation by talking about why certain…
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Larry is joined by historian and author Yuval Noah Harari in front of an audience at Live Talks L.A. to discuss his newest book, ‘Nexus: A Brief History of Information Networks From the Stone Age to AI.’ They begin their conversation by talking about the nature of information and how it's been manipulated throughout human history, starting with the…
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Larry is joined by journalist and host of CNN’s ‘NewsNight’, Abby Phillip, and they begin their conversation by discussing Donald Trump and his influence on the news media and the Republican Party. They then pivot to Kamala Harris and shine a light on her meteoric rise to the top of the Democratic ticket and break down the effectiveness of her medi…
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Larry weighs in on the debate between Donald Trump and Kamala Harris. He’s then joined by producer Will Packer to discuss his new Peacock limited series ‘Fight Night: The Million Dollar Heist’. They begin their conversation by discussing the premise and history behind the project, which leads to a discussion about the art of creating content in tod…
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Larry weighs in on the state of the presidential race and shares some of dates of his upcoming tour. He’s then joined by Sophia Cai from Axios and they begin their conversation by talking about Kamala Harris’s historic rise to Democratic presidential nominee and the change in party dynamics after Joe Biden dropped out of the race. They then examine…
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Larry is joined by actor, writer, and comedian Langston Kerman to talk about his brand new Netflix stand-up comedy special ‘Bad Poetry’, streaming on Aug. 20th. They begin their conversation by breaking down different types of comedy writing and examining Langston’s process when coming up with themes for a special. This leads to discussions about d…
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Larry weighs in on his favorite moments from the 2024 Olympics so far, Tim Walz, Trump’s wild press conference, and the state of Kamala Harris’s presidential campaign. He’s then joined by former world champion track-and-field athlete Marion Jones and they begin their conversation by discussing her journey from teenage phenom athlete to a star on th…
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Larry weighs in on this week’s attacks against Kamala Harris by the right-wing media. He’s then joined by Maryland Governor Wes Moore and they begin their conversation by discussing the many accomplishments Moore has achieved for his state, and the general mood of the Democratic Party after Joe Biden dropped out of the race and Kamala Harris steppe…
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Larry weighs in on Joe Biden dropping out of the presidential race. He’s then joined by professor, author, and entrepreneur Scott Galloway; they begin their conversation by discussing the art of doing interviews, the state of mainstream TV as a viable information source, and the schism between left and right political ideologies (16:47). They then …
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Larry weighs in on President Joe Biden. He’s then joined by director, playwright, and Emmy Award-winning actor Colman Domingo to discuss his latest film ‘Sing Sing’ (13:55). They begin their conversation by talking about the process of choosing roles for a project and describing the premise of ‘Sing Sing’, which centers around a group of prison inm…
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Larry is joined by comedian Bill Maher in front of a live audience at Live Talks L.A. to discuss his new book 'What This Comedian Said Will Shock You'. They begin by shining a light on how Bill compiled his favorite editorials from ‘Real Time with Bill Maher’ for the book and contrasting the focus of the hit HBO series with the celebrity-formatted …
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Larry is joined by writer, producer, and showrunner Janine Sherman Barrois to discuss her latest venture ‘The Big Cigar’ currently streaming on Apple TV+. They begin their conversation by discussing the difficulties of making a genuine high-budget biopic that features such a polarizing cultural icon like Huey Newton. Janine then shares what she lea…
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Larry is joined by actor and comedian Stephen Merchant and they begin their conversation by comparing the American and British versions of ‘The Office’, and sharing stories from making their respective iterations of the hit TV show. They then pivot to the Amazon Prime series ‘The Outlaws’ which recently premiered its third season and features Merch…
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Larry is joined by U.S. Representative from California’s 17th congressional district Ro Khanna and they begin their conversation by discussing the protest movement happening on college campuses around the U.S. and the principal factors contributing to the current conflict between Israel and Hamas. They then pivot to the congressional misconceptions…
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Larry is joined by attorney, political commentator, and host of 'The Bakari Sellers Podcast', Bakari Sellers, to discuss his new book ‘The Moment: Thoughts on the Race Reckoning That Wasn't and How We All Can Move Forward Now’. They begin their conversation by discussing the importance of relatability in politics and examining the level of this qua…
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Larry is joined by journalist and author Tiffany Cross and they begin their conversation by discussing the racial obstacles Tiffany faced during her time at MSNBC and how her passion for storytelling developed. They then dive into her new podcast 'ACross Generations with Tiffany Cross', and talk about how the show touches on, and attempts to bridge…
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Larry is joined by Oscar and Emmy Award-winning filmmaker and producer Ed Zwick to discuss his new memoir ‘Hits, Flops, and Other Illusions: My Fortysomething Years in Hollywood’. They begin by examining the state of the film industry against other forms of modern media and reflect on the importance of the movie-going experience in the 1970s and '8…
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Today, Larry reaches deep into the ‘Black on the Air’ Facebook, Twitter/X, and Instagram mailbags to answer some questions from some of you! Throughout the Q&A he weighs in on a myriad of burning topics including Donald Trump (11:30), the JFK assassination (24:18), ‘Cowboy Carter' (41:31), Louis Gossett Jr.(52:56), much, much more. Host: Larry Wilm…
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Larry is joined by journalist Taylor Lorenz to discuss the latest technology buzz, the state of internet culture, and her new podcast on Vox Media focusing on these subjects called 'Power User’. They begin their conversation by breaking down the recent congressional moves to ban TikTok and analyzing whether or not our representatives are correct to…
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Larry is joined by Emmy and Peabody Award-winning journalist Antonia Hylton to talk about her latest book ‘Madness: Race and Insanity in a Jim Crow Asylum’. They begin their conversation by talking about what inspired Antonia to write about the Crownsville mental health facility and the tribulations surrounding black mental health in the early part…
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Larry is joined by Emmy Award-winning and Oscar-nominated VFX supervisor Andrew Roberts to discuss his work on the movie ‘The Creator’ currently streaming on Hulu. They begin their conversation by breaking down the movie’s plot, examining Andrew’s creative approach to VFX, and detailing his collaboration process with director Gareth Edwards and pro…
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Larry is joined by Emmy Award-winning and Academy Award-nominated writer and director Cord Jefferson to discuss his newest film ‘American Fiction’. They begin their conversation by reminiscing about their time together on ‘The Nightly Show’ and marvel at the amazing journey that Cord's career has taken up to this moment. They then shift to ‘America…
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Larry is joined by Academy Award-nominated writer and producer David Hemingson to discuss his latest film ‘The Holdovers’. They begin the conversation by discussing the creative layers within the movie’s story structure and David’s working process with director Alexander Payne. They then dive into the deeply personal inspirations for each of the fi…
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Larry is joined by legendary filmmaker and actor Rob Reiner to discuss his 10-part podcast series titled ‘Who Killed JFK?’ currently available at iHeart and co-hosted by Soledad O’Brien. Rob begins by recalling when he first heard about the assassination of President John F. Kennedy and talking about how the ultra-famous murder mystery has continue…
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Larry is joined by writer Tina Nguyen and they begin their conversation by discussing Tina’s journalistic journey and what it was like working for Tucker Carlson. From Tucker’s disdain for her high school principal to firing her, Tina gives an insight on what Tucker the person is like (2:34). They then discuss why MAGA hasn’t embraced Ron DeSantis,…
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Larry starts the pod with a replay of a lovely conversation with his daughter, Lauren Wilmore, on the history and impact of the classic song "Have Yourself a Merry Little Christmas." He’s then joined by legendary director and producer Reginald Hudlin to discuss his new holiday film ‘Candy Cane Lane’, streaming on Amazon Prime, and give flowers to i…
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Larry is joined by journalist Donie O’Sullivan to discuss his new CNN documentary—‘Waiting for JFK: Reporting From the Fringe’—that aired on ‘The Whole Story With Anderson Cooper.’ They begin their conversation talking about how Donie was inspired to create a one-hour special on the fringe conspiracy group that formed in Texas who believe JFK and J…
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Larry pays tribute to friend and comedic legend Norman Lear by revisiting the very first ‘Larry Wilmore: Black on the Air’ episode, which features an in-depth interview with the iconic producer. Throughout the conversation they discuss Norman’s early days before his television career, the cultural impact of ‘All in the Family,’ and much more. Host:…
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Larry is joined by writer David Brooks in front of a live audience at Live Talks L.A. to discuss his new book ‘How to Know a Person: The Art of Seeing Others Deeply and Being Deeply Seen.’ They begin their conversation by discussing his personal journey and the life lessons that inspired him to write the book. They then dive into the lack of social…
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Larry is joined by Denver Film’s Kevin Smith (CEO) and Matt Campbell (Artistic Director) in front of a live audience at the 2023 Denver Film Festival. They begin their conversation with a brief history of Denver Film, a look at the curation process for the festival, and their thoughts on the state of the movie industry after the pandemic. Next, Lar…
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Larry is joined by Academy Award-winning filmmaker Errol Morris to discuss his new Apple TV+ documentary ‘The Pigeon Tunnel’ based on the memoir of the same name by spy novelist John le Carré. They begin by talking about the origins of the project and how his current promotional tour is inspiring Morris to analyze his famous interview style. This l…
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