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. A Poet’s Wild Past w/ Edward Hirsch

    6 DAYS AGO

    A Poet’s Wild Past w/ Edward Hirsch

    Acclaimed poet and Guggenheim Foundation president Edward Hirsch joins us in an unforgettable episode to discuss his powerful memoir My Childhood in Pieces: A Stand-Up Comedy and a Skokie Elegy. Hirsch reflects on his chaotic upbringing in 1950s Jewish Chicago, his complicated relationships with his parents, and the wild characters who shaped his life. He opens up about the tragic loss of his son Gabriel, how grief became poetry, and why humor and heartbreak often walk hand in hand. From poetic craft and emotional truth to the role of art in a distracted world, this is a raw, funny, and deeply moving conversation about identity, creativity, and resilience. Follow Paul on Instagram: https://www.instagram.com/paul_ollinger/?hl=en Check out "My Childhood" in Pieces: https://edwardhirsch.com/ Audio excerpted with permission of Penguin Random House Audio from MY CHILDHOOD IN PIECES by Edward Hirsch, read by the author. © Edward Hirsch ℗ 2025 Penguin Random House, LLC. All rights reserved.

    51 min

  2. 5 JUNE

    Has Affirmative Action FAILED? | Richard Kahlenberg & Paul Ollinger

    Has affirmative action failed in America?? In this eye-opening conversation, Richard Kahlenberg—author of Class Matters and a longtime education and housing policy scholar—explains why race-based affirmative action has failed America's working class and what can be done to fix it. A self-described “liberal maverick,” Kahlenberg dives into his controversial role in the Supreme Court case against Harvard, arguing that socioeconomic-based admissions would promote both racial equity and fairness without alienating the working-class voters Democrats are rapidly losing. From Harvard's legacy advantages and billionaire endowments to MLK’s and RFK’s forgotten views on class over race, this episode challenges elite institutions, political orthodoxy, and the future of education in America. Check out al of Richard's books and appearances: https://www.richardkahlenberg.org/ Get Paul's book: https://www.paulollinger.com/the-book

    53 min
  3. Facing Down Trump with Jocelyn Benson

    30 MAY

    Facing Down Trump with Jocelyn Benson

    In December 2020, Michigan Secretary of State Jocelyn Benson was decorating the family Christmas tree with her 5-year-old son when she heard a crowd outside her home chanting "Stop the Steal!" In the days and weeks that followed, Donald Trump harassed her on social media, calling for her arrest and accusing her of treason, Benson alleges.On this week's Reasonably Happy podcast, Benson--who is now running for governor--joins Paul Ollinger to discuss how she modernized the DMV, what it feels like to be targeted by the President of the United States, and why the Democrats' murky future. Paul pushes her to take a stand against a party that keeps falling on the sword of cultural issues with which most of America disagrees, opening the door for the very President who tried to intimidate her. Unfortunately, Benson waffles on subjects like biological males in girls' sports and the fact that most college campuses have been captured by progressive ideology. Still, it's an interesting conversation with a rising political star who, if she can stand up to her party the way she stood up to Trump, could be a solid mainstream candidate someday.Read Paul's Substack here: Http://words.paulollinger.com

    45 min
  4. Paul Wants $$ From Qatar (and other hilarious Substack posts)

    23 MAY

    Paul Wants $$ From Qatar (and other hilarious Substack posts)

    This week, Paul reads his three most recent Substack posts, including: A very funny take on Qatar's bribery of pretty much every institution in America, How his dog's feel about castration, and Why many of us will have our TikTok handles on our tombstones. Please join Paul's Substack family by following here: http://words.paulollinger.com . And, if you're so inclined, follow him on Instagram: https://www.instagram.com/paul_ollinger 00:00 Introduction to the Podcast and Substack 02:48 Exploring Qatar's Influence and Ethics 06:02 Proposal for a Qatari Comedy Club 08:57 Corporate Life Lessons from Dogs 12:00 Navigating Career Changes and Authenticity 18:11 The Impact of Social Media on Identity 23:10 A Humorous Obituary for the Future

    27 min

  5. 14 MAY

    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 Rob's Substack: https://www.robkhenderson.com/ Read Paul's Subtack: http://words.paulollinger.com Follow Paul on Instagram: https://www.instagram.com/paul_ollinger

    56 min

  6. 7 MAY

    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

  7. 30 APR

    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

  8. 23 APR

    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
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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
    286
  • Rating
    Explicit
  • Copyright
    Copyright © 2019-2024 Absolutely Huge Company, LLC. All rights reserved.
  • Show Website
    Reasonably Happy with Paul Ollinger

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