

Reasonably Happy with Paul Ollinger
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.
Episodes
Mentioned books

Jun 18, 2025 • 1h
Jeffery Toobin on Presidential Power | Reasonably Happy Podcast
CNN legal analyst and bestselling author Jeffrey Toobin breaks down the hidden power of presidential pardons — and how they reveal the true character of American presidents. From Trump’s transactional pardons to the controversial case of Hunter Biden, Toobin offers sharp analysis, historical insight, and headline-worthy commentary. He discusses why Gerald Ford’s Nixon pardon was unnecessary, how the January 6th pardons expose Trump’s political strategy, and why public cynicism is fueled by elite immunity. Plus, Toobin opens up about his career, love for golf, admiration for Jim Gaffigan, and his obsession with Evel Knievel’s wardrobe. This episode delivers sharp wit, surprising revelations, and crucial context for anyone interested in politics, justice, or power.
Follow Paul: https://www.instagram.com/paul_ollinger/?hl=en
Check out Jeffery's book: https://www.simonandschuster.com/books/The-Pardon/Jeffrey-Toobin/9781668084946

Jun 11, 2025 • 53min
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.

Jun 5, 2025 • 55min
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

May 30, 2025 • 46min
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

May 23, 2025 • 28min
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

18 snips
May 14, 2025 • 58min
From Chaos to Cambridge - Rob Henderson
Rob Henderson, author of 'Troubled: A Memoir of Foster Care, Family, and Social Class', shares his remarkable journey from a turbulent childhood in foster care to earning a PhD at Cambridge. He discusses the impact of instability on his education and emotional health, reflecting on military discipline as a transformative force. The conversation explores his concept of 'luxury beliefs' and how elite values can disadvantage the less privileged. Rob also delves into the importance of belonging, love, and the lessons learned from his past.

May 7, 2025 • 60min
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

Apr 30, 2025 • 46min
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

Apr 23, 2025 • 50min
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.

Apr 16, 2025 • 1h 13min
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/9781637746431Get Paul's Book: https://www.paulollinger.com/the-book


