Bill Maher and Two and a Half Men star Jon Cryer on border policies and media coverage, on how progressive issues influence elections, youth gender-affirming care, and social media “contagion” vs. authentic identity, how Jon grew up in a rough part of the Upper West Side, crime stories and colorful neighbors in 1970s–80s NYC, Jon’s acting journey, the podcast Jon produced, The Man Who Calculated Death, Jon’s on set experience with Charlie Sheen and how the show changed when Charlie relapsed, Elon Musk’s contributions to electric vehicles and space exploration vs. controversies regarding Twitter/X and political stances and much more!

Bill Maher and Sam Harris on why young women are dating older men, fashion & manufacturing in China, the nine-hour documentary Bill never saw, brands complicit with the wrong side of WW2, the banality of evil and how humans can rationalize horrific acts, how worldviews can make people do extreme things while feeling virtuous, Bill’s previous controversies, the recent report on the you-know-what virus, Bill’s raw milk theory, how once liberal media voices like Joe Rogan and Elon Musk were driven away by extreme politics, and the true equivalence of Elon’s wealth, which will blow you away.

Longevity guru Bryan Johnson (DON’T DIE is the #1 doc on Netflix) sits down with Bill for a great talk about whether it’s possible to live forever, anti-aging science, Bryan’s rigid routine that includes very controlled diet, sleep, and data-driven health interventions. Bill discusses his healthy routines while drinking and smoking and the guys differ on how much sacrifice is worth the potential gain. Also, stay tuned for Bryan’s “Johnson” measuring device during sleep, the importance of figuring out the actual age of your organs for longevity, how Bryan navigates his strict diet while out to dinner, and much, much more!

Bill and Matt Gaetz on the accusations against Matt, Bill’s preconception of Matt, Matt’s fandom of Politically Incorrect, how Matt supports both the NRA and the humane society, Bill’s take on hunting (not a fan), the economy of lonely, desperate men, Matt’s relationship with Joel Greenberg, and much, much more.

Bill and superstar Luke Bryan on the joys of Luke bow hunting with his family and how Bill just doesn’t get hunting, Luke’s Georgia upbringing and how it influenced his music, the songwriting scene in Nashville, genre collabs, the toll of Bill’s early party days, how Americans are more alike than different, wishing for a government solution for the “unhoused,” Luke’s tight knit group of friends, and much, much more.

Skepticism meets reflection when Bill invites Jay Shetty to share about a life that’s spanned the silence of a Vedic monastery and the spotlight of Hollywood. Jay explains how rising at 4 a.m. for cold showers, living under strict celibacy, and sleeping on the floor shaped his views on attachment and purpose. Bill probes everything from traditional therapy to modern dating, pushing Jay to clarify how one remains “spiritual” when fame and success come calling. They trade stories of long-term relationships, debate generational “softness,” and dig into whether the real mind-bender might be a vitamin D deficiency rather than any cosmic quest. There’s warmth in discovering their shared friendship with Arianna Huffington. The result is a candid conversation that balances humor, curiosity, and a surprising overlap of worldviews—one part cynicism, one part monk-like reflection.

Bill Maher sits down with former Colombo crime family capo, podcaster, and best-selling author Michael Franzese for a fascinating exploration of organized crime, current politics, and America’s shifting cultural landscape. From comparing Mafia code to modern government maneuvering, to dissecting the psychology of leaders, the two dive headlong into the forces shaping American life. Franzese shares candid reflections on his days running lucrative schemes (and why he ultimately walked away), while Bill challenges the notion of how power truly works. They also swap favorite scenes from The Godfather and Goodfellas, delve into Franzese’s religious awakening, how lessons from the mob world can translate into navigating business, politics, and personal relationships. Get ready for a raw, riveting sit-down that blurs the lines between comedy, true crime, and social commentary.

On this episode, Bill sits down with comedian, cultural provocateur and former neighbor Tom Green. The two recall the time Tom’s house burned down, why Tom is touring the country in a camper van, navigating public perception in the age of social media, Tom’s cancer treatment during his MTV fame and how a misdiagnosis almost derailed his health, getting fired on the Celebrity Apprentice, the blurred line between clever and stupid in comedy, his film Freddy Got Fingered, life on his Canadian farm, finding love, his latest documentary project and much more.

In this episode, Bill goes deep with legendary rapper, producer, and entrepreneur Xzibit—shedding light on his childhood as a military brat, the discipline that shaped his hip hop journey, and the inspiration behind his new album, “Kingmaker.” Xzibit opens up about chasing creative ambition while staying true to himself in an ever-shifting hip hop landscape, shares thoughts on social media’s addictive pull, and hip hop rivalries. He also reveals the hilarious story behind his fight scene with Jennifer Aniston in “Derailed,” complete with Brad Pitt lurking awkwardly in the background, and Bill recounts how one of Xzibit’s iconic lyrics made its way onto “Politically Correct” —a testament to Xzibit’s impact on both music and pop culture.

In this episode, Bill reconnects with rock-rap icon Kid Rock for his second round on Club Random—unpacking how they both manage to stay raw and honest in a world that loves to be outraged. Kid Rock talks about why he thought a Bud Light blow-up might be fun for social media. He also teases a new triple album (“Kid MF Rock”), wrestles with “woke” culture’s boundaries, and tries to sell Bill on the idea of finally meeting Donald Trump—complete with a tongue-in-cheek pitch for Elon Musk to carve Trump’s face onto Mount Rushmore. Bill, meanwhile, pushes back on Kid’s defense of Trump—especially around election denial—yet they bond over hating hypocrisy in both parties, not missing shows, and embracing the backlash that comes from speaking your mind. It’s a no-filter chat with two guys who, despite their differences, can’t help but find plenty of common ground.

On this episode, Bill is joined by veteran broadcaster and cultural commentator Don Lemon. The two discuss Don’s transition away from CNN and his new foray into streaming, the shifting landscape of media bias and viewer trust, the lure of unfiltered conversation versus traditional “managed” television formats, and the political tightrope walk of modern journalism. They candidly dive into everything from Don’s experiences as a gay Black man in the public eye and meeting his husband, diversity and inclusion in hiring, the mystique of AOC, “defund the police,” and how Democrats might counter the MAGA movement without veering into extremes. They also weigh in on the comforts (and occasional perils) of personal freedom. All this, plus reflections on life in New York vs. Los Angeles, the ups and downs of public perception, and much more.

On this episode, Bill is joined by stand-up comic and podcast provocateur Andrew Schulz. The two swap stories about Andrew’s transition into fatherhood (including fertility hurdles and the emotional roller coaster of IVF), the perils of fame in the digital age, why he once called Fox News out on its overblown “outrage” stories, negotiating free speech in comedy and the ever-shifting rules of social discourse, meeting fans where they are online. They debate America’s “abundance mentality” and how it informs politics, the decline of open discussion in modern media, the rise of cancel culture (and how both the left and right weaponize it), the fine line between comedic license and genuine offense, Elon Musk’s takeover of Twitter, and the peculiarities of personal relationships in the spotlight. They also trade observations on religion, Trump’s enduring appeal, social media mobs, bizarre magazine collections from New York City newsstands, and much more.

On this episode, Bill sits down with New York Times columnist Maureen Dowd for a wide-ranging, personal chat about her new book “Notorious"—a collection of her incisive profiles of major cultural and political figures—and why she once went viral for a botched edible experience in Denver. The two swap stories about growing up in Washington, D.C. (her father was a detective), how “woke” culture may have dampened the fun on the left, and what still draws voters to Donald Trump’s brash humor. Maureen recalls the times she’s gone toe-to-toe with politicians across the aisle, and she and Bill debate whether Democrats need a showman of their own. Throughout it all, they reflect on the challenges of bridging America’s political divide, the strange alliances they’ve formed in the process, and how a good dinner party could be the real key to bringing people back together.

On this episode, Bill catches up with journalist Chris Cuomo. They get into Chris’s current life since his CNN exit, why he’s suing to clear his name, and reflect on the media’s “scalp-hunting” mentality. Chris opens up about growing up in a political dynasty under his father Mario and working closely with his brother Andrew, how policy fights don’t always match party ideals, and what it’s like navigating scandal in a 24/7 news cycle. They swap thoughts on Trump’s flair for the dramatic, America’s appetite for outrage, the “defund the police” debate, how we lost the art of joking about sensitive topics, and why it’s vital to push back against extremes on either side. Throughout the conversation, Bill and Chris find common ground in calling out hypocrisy, highlighting nuance in politics, and believing we shouldn’t judge people by their worst moments—and they close out with some friendly banter on self-defense, fatherhood, and the value of letting go of grudges.

On this episode, Bill sits down with musician, podcaster and one-time Mumford & Sons banjoist Winston Marshall. The two reflect on Winston’s departure from the band following a social media firestorm over a controversial book endorsement, how that ordeal exposed the intense pressures of “cancel culture” within the music world and why Winston ultimately decided to speak his mind despite the fallout. They dig into England’s shifting cultural landscape, the rise of political correctness in both the UK and America, what it’s like to navigate taboo topics in today’s hyper-partisan climate, Bill’s own battle with early 2000s cancellations, the nuance of “platforming” divisive guests in media, and how comedic irreverence can serve as a release valve against excessive wokeness. They also touch on London’s changing face, the lure of extremist ideologies, the importance of honest dialogue across the political spectrum and much more.

On this episode Bill welcomes Turning Point USA founder and conservative firebrand Charlie Kirk. The two sit down for a long‑form, surprisingly cordial debate that roams from identity politics to faith, personal freedom, and the state of American institutions. They spar over marijuana, public safety, the limits of adult choice—topics that segue into bigger clashes over homelessness policy, whether safe‑injection sites help or hurt cities, and if Ivy League schools ought to be razed and rebuilt from scratch. A lot of ground is covered in this thoughtful back and forth, plenty of laughter and even a spit-take or two.

On this episode, Bill hangs out with actor Terrence Howard for a free-wheeling chat that bounces between Hollywood and big ideas. Terrence speaks about clashing with studios over money, why Empire was both a blessing and a headache, and how an early brush with Richard Dreyfus taught him to fight for every scene. He and Bill riff on environmental junk in our food and air, and Terrence’s belief that music tuned to 432 Hz could reshape everything from space travel to human longevity. Along the way they trade Hendrix trivia, swap stories about celebrity parties and canceled careers, and agree that nailing a close-up still feels like magic.

On this episode Bill hangs out with author-podcaster Lewis Howes for a free-wheeling chat about life choices and staying sane. They swap stories on moving to L.A., falling in (and out of) love, and how childhood baggage can push you toward self-improvement—or self-destruction. Bill explains why he’s happily child-free and “married to the job,” while Lewis talks about healing old trauma without drugs or alcohol. They poke at big questions—meds vs. mind-body fixes, meat vs. veggies, woke kids vs. baffled parents—and laugh over a possible 98-year-old tortoise adoption, and Bill’s headline-grabbing dinner with Trump. Mostly, it’s two guys comparing notes on how to stay curious, healthy-ish, and kind of normal in a crazy world.