Reasonably Happy with Paul Ollinger

Paul Ollinger
Reasonably Happy with Paul Ollinger

Comedian Paul Ollinger wants you to be happy but let’s not go crazy here, okay? In his new show, Reasonably Happy: the Skeptic’s Guide to Achievable Contentment (fka Crazy Money), Paul will help you find authentic fulfillment through candid conversations with comedians, authors, celebrities, and other remarkable guests who share their failures and foibles, anxiety and addiction, and their grand vision of life that keeps them pushing forward.

  1. 2D AGO

    From Chaos to Cambridge - Rob Henderson

    He was drinking by age five, shuffled through ten foster homes, and emotionally shut down by the time most kids are starting kindergarten — yet Rob Henderson clawed his way from chaos to Cambridge. In this powerful episode, Rob, author of Troubled: A Memoir of Foster Care, Family, and Social Class, shares his incredible journey from trauma and addiction to earning a PhD from Cambridge University. He opens up about childhood instability, military discipline, elite university culture, and his groundbreaking concept of “luxury beliefs”—status-signaling values held by the privileged that often harm the poor. This conversation is raw, eye-opening, and packed with insights about resilience, class, and what truly shapes success. Check out Robs Substack: https://www.robkhenderson.com/ Check out Pauls Book: http://paulollinger.com/the-book

    56 min

  2. MAY 7

    Mike Reiss: How The Simpsons Changed TV | Reasonably Happy with Paul Ollinger

    The Simpsons writer and showrunner Mike Reiss shares behind-the-scenes secrets from 36+ years on the iconic animated series. From working with comedy legends like Sam Simon, Al Jean, and Conan O'Brien to writing for Johnny Carson and witnessing the wild beginnings of FOX, Mike recounts hilarious Hollywood stories and life lessons from his travels to 147 countries. He reveals the origin of the Simpsons, why Harvard wasn’t funny, how VCRs and fan feedback helped shape the show, and why the writers’ room was like a "kibbutz but more Jewish." It’s a deep dive into comedy, creativity, and the wild ride of creating a global phenomenon. Follow Mike's Substack: https://substack.com/@mikereiss Get Paul's Book: https://www.paulollinger.com/the-book

    58 min

  3. APR 30

    Laurie Woolever- Dark Side of Celebrity Chefs

    Former personal assistant to both Anthony Bourdain and Mario Batali, Laurie Woolever, opens up about the untold truths behind celebrity kitchens, toxic food culture, addiction, and what ultimately drove Bourdain to suicide. From Mario Batali’s manipulative power plays to Bourdain’s romantic obsessions and lifelong depression, Woolever shares the unfiltered story behind her new memoir Care and Feeding. The conversation also explores alcoholism in fine dining, working through shame, and the ethics of telling personal stories—alongside hot takes on The Bear, Lucky Charms, and how Batali allegedly didn't pay staff. This is a must-watch for anyone fascinated by the dark underbelly of fame, food, and finding your voice after chaos. Check out Laurie's podcast: https://www.instagram.com/carbfacepod/ Get a copy of Paul's book: https://www.paulollinger.com/the-book

    45 min

  4. APR 23

    E.A. Hanks - Famous Father, Troubled Mother

    In this raw and revealing episode of Reasonably Happy, author and screenwriter E.A. Hanks opens up about growing up as the daughter of Tom Hanks, surviving a chaotic childhood with an abusive, mentally ill mother, and forging her own path in Hollywood. From hidden trauma and therapy breakthroughs to the price of fame and writing a memoir about family, identity, and the open road, Hanks shares powerful stories behind her new book The Ten. She discusses how her father’s fame created emotional distance, the collapse of her mother’s mental health, and how writing became both her refuge and rebellion. If you're into celebrity legacies, healing childhood wounds, or the grind of making it as a writer in L.A., this episode hits every note.

    48 min

  5. APR 16

    Jim Lampley- Boxing, Fame & Fallout | Reasonably Happy with Paul Ollinger

    Legendary sportscaster Jim Lampley joins Paul Ollinger on "Reasonably Happy" to share unforgettable stories from his 40+ year broadcasting career, covering everything from Olympic Games and Super Bowls to boxing icons like Muhammad Ali and Mike Tyson. Lampley reveals the behind-the-scenes drama of his rise at ABC Sports, recounts his emotional connection to the Miracle on Ice, and reflects on the values learned from greats like Billie Jean King, Arthur Ashe, and Howard Cosell. From interviewing George Mira to being thrust into the spotlight by Roone Arledge, Jim discusses ego, failure, reinvention, and finding happiness through storytelling. His new memoir It Happened: A Uniquely Lucky Life in Sports is a masterclass in perseverance and passion—this conversation is a must-watch for sports fans, storytellers, and anyone chasing purpose. Get Jim's Book: https://www.simonandschuster.com/books/It-Happened!/Art-Chansky/9781637746431 Get Paul's Book: https://www.paulollinger.com/the-book

    1h 11m

  6. APR 9

    Jane Borden- Cults Like Us | Reasonably Happy

    In this thought-provoking episode of Reasonably Happy, Paul Ollinger sits down with journalist and author Jane Borden to unpack her explosive new book Cults Like Us: Why Doomsday Thinking Drives America. Together, they explore how apocalyptic beliefs, religious extremism, and cult-like behaviors have shaped American identity—from Puritan roots to modern political movements like MAGA. Jane reveals how tribal psychology, anti-intellectualism, and the prosperity gospel fuel division, and why both the far right and far left are vulnerable to cultish thinking. With dark humor, candid insights, and a deep dive into American history, this episode is a must-watch for anyone curious about religion, politics, and the future of democracy. Check out Janes book: https://www.simonandschuster.com/books/Cults-Like-Us/Jane-Borden/9781668007808 Get Pauls Book: https://www.paulollinger.com/the-book

    52 min

  7. APR 2

    Life at Fox News w/ Jessica Tarlov | Reasonably Happy with Paul Ollinger

    In this episode of Reasonably Happy, Paul Ollinger sits down with Fox News contributor and Raging Moderates co-host Jessica Tarlov for a wide-ranging conversation on politics, media bias, Israel, parenting, and the chaos of air travel. Jessica opens up about raising two young kids, finding peace in Jamaica, and holding her own as the lone Democrat on The Five. They dive into the latest national security scandal involving leaked attack plans, the challenge of moderate voices in polarized media, anti-Semitism on the left, and what’s really holding back immigration reform. It’s an honest, thoughtful, and funny episode that blends politics with real life. Get Pauls book: https://www.paulollinger.com/the-book

    52 min

  8. MAR 26

    Too Woke to Joke w/ Jeff Maurer | Reasonably Happy Podcast

    In this episode of Reasonably Happy, comedian and writer Paul Ollinger sits down with former Last Week Tonight writer Jeff Maurer for a razor-sharp, no-holds-barred conversation on comedy, politics, and the state of liberal discourse. Maurer, now the voice behind the acclaimed Substack I Might Be Wrong, unpacks his journey from speechwriter to Emmy-winning TV writer, and why he left Hollywood to pursue independent commentary. They dive deep into the culture wars, media bias, the Biden dilemma, and what today's Democratic Party can learn from the Obama era. With sharp wit and refreshing honesty, Maurer discusses the left’s loss of self-awareness, the problem with orthodoxy, and how free speech is under siege from all sides. If you're tired of political echo chambers and crave a blend of humor and intellect, this one's for you. Get Pauls book! https://www.paulollinger.com/the-book Check out Jeffs Substack: https://substack.com/@imightbewrong

    1h 1m
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Trailer

4.9
out of 5
433 Ratings

About

Comedian Paul Ollinger wants you to be happy but let’s not go crazy here, okay? In his new show, Reasonably Happy: the Skeptic’s Guide to Achievable Contentment (fka Crazy Money), Paul will help you find authentic fulfillment through candid conversations with comedians, authors, celebrities, and other remarkable guests who share their failures and foibles, anxiety and addiction, and their grand vision of life that keeps them pushing forward.

Information

  • Creator
    Paul Ollinger
  • Years Active
    2019 - 2025
  • Episodes
    282
  • Rating
    Explicit
  • Copyright
    Copyright © 2019-2024 Absolutely Huge Company, LLC. All rights reserved.
  • Show Website
    Reasonably Happy with Paul Ollinger

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