Gina Gershon on Fame, Desire, and Boobs

Gina Gershon on Fame, Desire, and Boobs

Author: Paul Ollinger March 5, 2026 Duration: 1:00:42
Guess who I got to meet last week - Gina Gershon. That’s right, the incredibly beautiful and talented actress, author, singer, and long-standing disruptor of polite expectations. You know Gina from unforgettable roles in Bound, Showgirls, Face/Off, Cocktail, and a career that has zig-zagged fearlessly between Hollywood glamor, indie grit, Broadway, and music. We talked about her work and life as recounted in her new memoir, 'Alpha Pussy: How I Survived the Valley and Learned to Love My Boobs’ (a title that caught the attention of my 16 year-old son and, well, me). Gina shares stories about Prince, David Mamet, Paul Thomas Anderson, Robert Altman, Michael Mann, and Lou Reed. And she spills the beans about kissing both Tom Cruise and Jennifer Tilly (I’d go with Jen, personally). Oh, she also tells why it was so much fun to improv with Larry David on 'Curb Your Enthusiasm’. Need I say more? Okay, yes - just a little: What I took away from this interview is that artists like Gina who prioritize freedom above commerce sometimes miss out on millions of dollars and a degree of “stardom,” but they maintain their sense of self and Alpha vibe. Check it out.




Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ ⁠HERE⁠⁠  (DO IT!)

Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ ⁠HERE⁠ 

Buy Gina's book HERE.

Get full access to Reasonably Happy at words.paulollinger.com/subscribe

Paul Ollinger has worn a few different hats-stand-up comedian, tech executive, and now, the curious host of Reasonably Happy with Paul Ollinger. This isn't a lecture series or a dry self-help guide. Instead, it feels more like pulling up a chair for a series of genuinely engaging talks that wander into the places where our daily lives, careers, and inner worlds collide. The conversations, which feature authors, thinkers, and various creatives, are refreshingly candid. They dig into the practical and philosophical questions about what it actually means to build a life that feels both successful and satisfying. You'll find that each episode of this podcast approaches big themes-money, purpose, and the pursuit of contentment-with a blend of wit and thoughtful depth. The underlying idea isn't about finding a perfect, Instagram-ready version of happiness, but something more grounded and attainable. It's for anyone who's ever wondered if there's a smarter, more meaningful way to navigate the pressures of business and culture without losing sight of what matters. Tuning in, you get the sense that Paul is figuring it out alongside his guests, making the insights feel earned and relatable. The result is a consistently interesting exploration of how we can all aim for a life that feels reasonably, and authentically, well-lived.
Author: Language: English Episodes: 100

Reasonably Happy with Paul Ollinger
Podcast Episodes
How to Live a Stress-free Financial Life with Jared Dillian [not-audio_url] [/not-audio_url]

Duration: 1:00:00
Financial gurus like Dave Ramsey or Suze Orman tell their audience that the key to achieving wealth—or just financial stability—is to cut back on the little things like that daily Starbucks latte. Jared Dillian thinks th…
Judd Apatow on Money, Fame, and Adam Sandler (Encore) [not-audio_url] [/not-audio_url]

Duration: 48:26
Judd Apatow is one of the most important figures in comedy and film today. But he just doesn’t care that much about money. This non-attachment to material goods leaves him more time to focus on what matters: writing, dir…
Author Gary Sernovitz [not-audio_url] [/not-audio_url]

Duration: 59:08
Gary Sernovitz is one of the funniest financial writers working today. His hilarious new novel The Counting House tells the story of a university’s Chief Investment Officer who is suffering a mid-life crisis. If you poss…
How to Get Un-stuck with Merrick Furst, Ph.D. [not-audio_url] [/not-audio_url]

Duration: 1:06:24
Do you ever feel stuck in life? As if you are in the wrong place or you’re in the right place but doing the wrong thing? What do you do when you find yourself at a crossroad? Today, I speak to innovation expert Merrick F…
Paul Reads His Thanksgiving Essays [not-audio_url] [/not-audio_url]

Duration: 35:41
In this special “over the river and through the woods” episode, Paul reads four of his latest pieces from his Substack, Money and the Meaning of Life, so that you can drive or workout without reading. Latest posts includ…
Ed Begley Jr. on Finding Serenity in Hollywood [not-audio_url] [/not-audio_url]

Duration: 38:45
✍️ Subscribe to Paul’s Substack ‘Money & the Meaning of Life’ here. ✍️🎤 See Paul’s upcoming comedy dates here and random thoughts on Instagram here. 🎤Ed Begley Jr. has been acting professionally since 1967 when he appear…
Lessons from an '80s Guitar god with Rik Emmett of Triumph [not-audio_url] [/not-audio_url]

Duration: 1:05:15
Rik Emmett is a vocalist, guitarist and former member of the rock band Triumph, which earned 18 gold and nine platinum records in Canada and the United States in the late 1970s and early’80s. Triumph was known for its BI…
The NHL, Brain Injury, and Psilocybin with Daniel Carcillo [not-audio_url] [/not-audio_url]

Duration: 50:17
When Daniel Carcillo played in the NHL, he was known as an enforcer so tough and volatile that he earned the nickname “Car Bomb.” In his 12 seasons in the NHL, Daniel was a member of two Stanley Cup-winning teams (2013 a…

«1...678910