Club Random with Bill Maher

Sean Penn returns to Club Random for another wild ride with Bill Maher. From kissing James Franco in Milk to drone warfare in Ukraine, the conversation covers it all, politics, war, Hollywood, and even AI going rogue. Sean opens up about his documentary Superpower, Putin’s ambitions, America’s contradictions, and what it means to live fully in a broken world.

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ABOUT CLUB RANDOM

Bill Maher rewrites the rules of podcasting the way he did in television in this series of one on one, hour long conversations with a wide variety of unexpected guests in the undisclosed location called Club Random. There’s a whole big world out there that isn’t about politics and Bill and his guests—from Bill Burr and Jerry Seinfeld to Jordan Peterson, Quentin Tarantino and Neil DeGrasse Tyson—talk about all of it. 

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Bush frontman Gavin Rossdale drops by Club Random to chat with Bill Maher about his new album “I Beat Loneliness,” the craft of songwriting, touring life, dad duties, aging like a rock star, mental health, religion, AI paranoia - and yes, a little life advice from David Bowie himself.

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David Mamet and Bill Maher cover a lot of ground this spirted conversation, discussing Mamet’s recent film Henry Johnson, his upcoming projects including a novel on education and a film about Abraham Lincoln, the 2020 election, media bias, foreign interference in U.S. elections, Trump’s leadership style, gender policies in sports, the state of California governance, conspiracy theories surrounding the Kennedy assassination, the Zapruder film controversy, UFO sightings, AI and technology’s impact on society, parenting and discipline in education, the decline of common sense, streaming platforms and the film industry.

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Bill Maher sits down with Tim Pool host of The Culture War Podcast for a conversation on health, aging and the bizarre wellness trends sweeping the culture to the impact of media polarization, the manipulation of public perception, generational divides in politics, the rise of wokeness, and the cultural shifts defining Gen Z and Gen Alpha, the challenges of marriage and masculinity in a rapidly changing world, the decline of skateboarding in America, and the fragmentation of entertainment in the digital age.

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On this episode, Bill sits down with fitness icon, wellness entrepreneur and straight-talking firebrand Jillian Michaels. Bill and Jillian settle in for a free-wheeling chat that drifts from lighthearted ribbing to debates about public health, politics, and pop culture. One minute they’re laughing about early-morning phone alerts or swapping travel stories; the next, they’re chewing over whether either political party still speaks to the middle. Big personalities and bigger opinions collide, but beneath the jokes they keep circling the same question: how do we stay sane—and a little healthier.

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Bill Maher sits down with Tony Hinchcliffe, the ringmaster behind the hit live podcast Kill Tony. Tony reminisces about his early days answering phones at the Comedy Store, how Mitzi Shore ruled the club, how talent coordinators silently decide careers, the jelly fish ghost in the Belly room, Tony’s Puerto Rico joke at the Trump rally and the social media blowback, doing stand-up in a parking lot during Covid, Austin’s comedy boom, Kid Rock’s ‘Southern White House”, why comics crave honesty, Bill’s brief detour into the history of Genghis Khan, and so much more. 

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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.

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Introducing Michelle Obama and Craig Robinson: Break the Generational Patterns Holding You Back (How to Build Confidence, Responsibility, and Emotional Resilience) from On Purpose with Jay Shetty.

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Can you remember the first time you felt truly in charge of your own decisions?

What’s one thing you picked up from your family that you wish you could unlearn?

In this heartfelt episode, Jay Shetty sits down with former First Lady Michelle Obama and her brother, coach and mentor Craig Robinson, for an intimate conversation centered around family, resilience, and the lasting impact of love and connection.

Michelle and Craig reminisce about the powerful values instilled by their parents, a deep sense of independence and unwavering family loyalty. Even through financial struggles, their parents cultivated a home filled with trust and safety, making it clear that family would always be a source of strength. Memories of birthdays around the kitchen table, houses bustling with extended relatives, and the steady presence of grandparents and cousins all contributed to a lifelong sense of belonging and support that continues to influence their lives.

As they journeyed into adulthood, both Michelle and Craig relied on therapy, genuine friendships, and a strong community to help them face life’s transitions, grief, and the many complexities of growing up. Michelle shares how seeking guidance and embracing self-reflection, especially during moments of change, has been central to her personal growth, demonstrating the value of openness, adaptability, and continuous learning throughout every stage of life.

In this interview, you'll learn:

How to Foster Family Unity During Tough Times

How to Nurture Independence in Children

How to Unlearn Limiting Beliefs from Your Upbringing

How to Create Safe Spaces for Honest Conversations

How to Teach Empathy Through Parenting

How to Balance Protection and Freedom as a Parent

How to Normalize Therapy and Emotional Support

Their conversation is a moving testament to the impact of compassion, authenticity, and purposeful living, a reminder that life’s greatest challenges can be met with empathy, courage, and hope.

With Love and Gratitude,

Jay Shetty

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Join Jay for his first ever, On Purpose Live Tour! Tickets are on sale now. Hope to see you there!  

What We Discuss:

00:00 Intro

02:00 The Kind of Love Only Siblings Understand

04:15 What was the First Secret You Shared With Each Other?

09:53 Raised To Be Independent Children In A Loving Community

14:55 How Different Generations Celebrate Birthdays

17:00 How to Unlearn Your Inner Fears

19:47 The Fear Of What Could Happen Can Hinder Personal Growth

25:28 What a Childhood Encounter with Police Taught Me About Bias

29:35 Being Judged By The Color Of Your Skin

31:54 Racism Is Still An Issue

34:07 How to Raise Resilient Children

35:59 Don't Make Assumptions Based On Your Emotions

38:17 Don't Let Negative Thoughts Dictate Your Actions

40:48 The Power Of Good Parenting

48:41 How To Prioritize Being A Parent While Chasing Your Dreams

52:08 Parents Aren't Responsible For Their Children's Happiness

58:07 Focus On Cultivating Independence in Your Children

01:02:24 What Is Your Form Of Therapy?

01:11:08 Are You Doing Enough?

01:16:10 How To Become A Good Parent

01:37 What Would Your Mother Be Most Proud Of?

Episode Resources:

Michelle Obama | Instagram

Michelle Obama | Facebook

Michelle Obama | YouTube

Michelle Obama | Books

Obama Foundation 

The Light We Carry: Overcoming in Uncertain Times

Craig Robinson | Instagram 

Craig Robinson | X

IMO with Michelle Obama and Craig Robinson

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DISCLAIMER: Please note, this is an independent podcast episode not affiliated with, endorsed by, or produced in conjunction with the host podcast feed or any of its media entities. The views and opinions expressed in this episode are solely those of the creators and guests. For any concerns, please reach out to [email protected].

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.

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Introducing Deepak Chopra: How to Ask AI The RIGHT Questions To Grow, Heal, and Live a More Fulfilled Life from On Purpose with Jay Shetty.

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Do you ever feel like you're just going through the motions?

Do you ever feel lonely even when you're around people?

Today, Jay welcomes back the legendary Deepak Chopra after six years, to discuss the unexpected intersection of spirituality and artificial intelligence. Together they unpack the beautiful blend of ancient wisdom and cutting-edge innovation.

Jay reflects on his first meeting with Deepak and how their bond has evolved over the years. The conversation quickly flows into one of the most fascinating questions of our time: Can AI actually support our spiritual growth, rather than distract from it? Deepak shares his insights on the mysteries of the universe, the unseen forces that shape our reality, and why he believes consciousness, not matter, is the foundation of everything.

Jay and Deepak break down the fears surrounding AI, from misinformation to war, and why it’s so important for us to grow spiritually alongside our technology. They explore how storytelling, creativity, and love are deeply human qualities that no machine can replicate, and how we can use these gifts to shape a better, more compassionate world.

In this interview, you'll learn:

How to Ask AI Better Questions to Unlock Wisdom

How to Use Technology to Support Emotional and Physical Healing

How to Find Purpose Through the Art of Storytelling

How to Train AI to Reflect Inclusivity and Diversity

How to Embrace Consciousness as the Foundation of Reality

How to Create a Sacred Relationship with Technology

Deepak reminds us that the answers we’re looking for often begin with a better question. And with the right mindset, even the most advanced technology can become a tool for inner transformation and collective healing.

With Love and Gratitude,

Jay Shetty

Join over 750,000 people to receive my most transformative wisdom directly in your inbox every single week with my free newsletter. Subscribe here. 

Join Jay for his first ever, On Purpose Live Tour! Tickets are on sale now. Hope to see you there! 

What We Discuss:

00:00 Intro

01:41 What If the Universe Is Just a Giant Digital Simulation?

12:36 How to Train AI to Unlock Ancient and Hidden Knowledge

13:39 Blending AI and Spirituality to Understand Consciousness

18:23 Could AI Really Lead to Human Extinction?

22:34 What’s Actually Holding Humanity Back From Progress?

23:37 How the Human Brain Transformed Over Time

26:11 The 2 Things That Set Humans Apart From All Other Species

27:16 Can Technology Lead Us to True Peace and Prosperity?

28:10 Will AI Replace Our Jobs or Unlock Human Creativity?

30:46 Do You Think AI Can Ever Have a Soul?

31:45 The Gender and Racial Bias Hidden in AI Systems

32:33 How to Build More Inclusive and Equitable AI Models

33:32 Why a Shared Vision Can Solve Any Problem We Face

36:13 Would You Trust AI to Know You Personally?

36:57 How You can Use AI to Get Better Sleep

37:29 Can AI Actually Give You Good Relationship Advice?

38:07 How AI Can Help You Find and Nurture Love

38:29 Why Personal Growth Solutions Should Never Be Generic

39:41 Your DNA Holds the Footprints of Human History

42:33 Rethinking the Big Bang: What Science Still Can’t Explain

44:31 Is Everything You See Just a Projection?

47:48 Why Fear of the Unknown Limits Our Growth

48:52 Want Better Answers? Ask Better Questions

51:41 The True Secret to Longevity Isn’t What You Think

54:30 How Your Brain Turns Experience Into Reality

55:08 Why Consciousness Is Still Life’s Greatest Mystery

56:28 The First Question You Should Always Ask AI

58:38 How ChatGPT Can Spark Deeper, More Intelligent Questions

Episode Resources:

Deepak Chopra | Website

Deepak Chopra | Instagram 

Deepak Chopra | TikTok 

Deepak Chopra | Facebook

Deepak Chopra | YouTube

Deepak Chopra | X

Digital Dharma: How AI Can Elevate Spiritual Intelligence and Personal Well-Being

See omnystudio.com/listener for privacy information.

DISCLAIMER: Please note, this is an independent podcast episode not affiliated with, endorsed by, or produced in conjunction with the host podcast feed or any of its media entities. The views and opinions expressed in this episode are solely those of the creators and guests. For any concerns, please reach out to [email protected].