Sunday Sitdown with Willie Geist

Guest: Billy Crystal
Episode Title: Billy Crystal Reflects on ‘When Harry Met Sally’ and Studying Under Scorsese
Date: August 24, 2025
Location: Jack Crystal Theater, NYU Tisch School of the Arts

Episode Overview

Willie Geist sits down with Billy Crystal for a heartfelt, wide-ranging conversation set in the theater named after Crystal’s late father—the Jack Crystal Theater at NYU's Tisch School. Together, they reflect on Crystal’s legendary career, his roots in show business and jazz, formative influences like Martin Scorsese, and the impact of enduring works such as “When Harry Met Sally” and his acclaimed stage show “700 Sundays.” Crystal also opens up about his latest turn—a dramatic television role in the Apple TV miniseries “Before”—and the evolution of his career, family, and lasting friendships.

Key Discussion Points & Insights

1. The Significance of the Jack Crystal Theater

• [04:02] Billy recounts his childhood memories of the venue, originally a jazz concert hall (the Central Plaza), where his father, Jack Crystal, produced regular jazz sessions:

  “This place was a catering hall ... known as the Central Plaza. And the Sessions were called Jazz at the Plaza ... I was five. I ran up on stage and tap danced with the band as best I could. Crowd went wild. ... It always stayed with me.” —Billy Crystal

• His father’s efforts to integrate musicians and create a true melting pot of talent made a lasting impression.
• The theater’s transformation, honoring his father’s legacy, holds deep emotional meaning for Billy and shaped his future in performing arts.

2. The Power of First Applause

• [05:54] On the memory of performing as a child:

  “You never forget your first laugh, your first applause ... it just drove me and it still does to this day.” —Billy Crystal

3. The New Series: “Before” on Apple TV

• [07:58] Describing his dark dramatic role in “Before”:

  “It’s a psychodrama thriller ... a man who's losing his mind in order to find himself ... a surreal world that'll make total sense right at the very end of the 10 episodes.” —Billy Crystal

• Billy was one of the show’s creators and found inspiration from family history and stories of past-life memories in children.
• The genesis: what began as a story inspired by his grandmother’s tapes evolved into a psychological drama after reading “Life Before Life.”
• [09:44] On taking the lead role:

  “I was going to produce it ... but when I heard Sarah Thorpe’s pitch ... I said, stop, I'll play him. I want to play him.” —Billy Crystal

4. Acting Process and Emotional Immersion

• [13:06] On living with the character Dr. Eli Adler:

  “I really developed a method for me which I hadn’t had to have before. I couldn’t shake him ... I was so immersed in Eli and fearless in what I would do.” —Billy Crystal

• The role’s intensity led to long days, solitary nights, and a transformation that was difficult to shed.

5. Working with Young Talent

• [16:28] On Jacoby Jupe, who plays Noah:

  "He's an extraordinary kid ... has a natural instinct about him. That's very rare ... In the first half of the series, he doesn’t speak much ... and then he’ll go, ‘Could I have a cruller?’ I mean, he just turns it on and off.”

• The show auditioned over 700 kids before finding Jupe.

6. Television as a New Frontier

• [20:04] On embracing the limited series format:

  “It’s like five hours of television, and then you’re on to the next thing ... Maybe there’s talk of a second season ... I had a great time at this point in my life ... to find something new and so invigorating is really thrilling.”

7. Lifelong Love of Performance

• [23:22] Reflecting on his earliest ambitions:

  “It was all before ... My brothers and I with the relatives performing ... we had a show called the Swing show ... and I did stand up in it and it just sort of came naturally. ... Always has been the safe place." —Billy Crystal

• Studying under Martin Scorsese at NYU, learning intensity and storytelling in film.

8. Influences and Breakthroughs

• Stories from early standup days, encouragement from his wife Janice, and performing at Catch a Rising Star.
• [29:20] The turning point:

  “We have a baby. ... Janice comes to me and says ... I’ll go back to work ... you’ll watch Jenny all day ... and you’ll be the comedian I know you can be. ... That was the deal. ... And I found with Jenny that you can love something so much more than yourself.” —Billy Crystal

9. Muhammad Ali & Hollywood Breaks

• [33:54] The chance imitation performance at Ali’s roast evolved into a 40-year friendship:

  “Ali grabs me and whispers in my ear, ‘You’re my little brother.’ And that’s what he called me for 42 years.”

• The importance of fate and seizing opportunities in his rise (“What if Robert Klein was in town? ... Maybe none of it happens.”)

10. Enduring Impact of “When Harry Met Sally”

• [44:41] On its timeless appeal:

  “There’s so much truth and love in that movie ... it’s thrilling that it still happens ... you never know.”

• How the famous line was invented:

  “And I said, then we’ll cut to a woman, an older woman, and she’ll say, ‘I’ll have what she’s having.’ And that’s how that happened.” —Billy Crystal [49:23]

11. Creating “700 Sundays” and Processing Grief

• [50:12] On writing and performing his one-man show about his father:

  “The luggage gets heavy, carrying it around all that time ... I just needed to do it in a way I was comfortable with, and that’s in front of people ... It was the most amazing experience ... putting a face on grief ... you turn it into something that’s art.” —Billy Crystal

• The show’s deep resonance with audiences and the emotional fulfillment it brought him.

12. Legacy, Family, and Reflections

• [53:38] On his father’s lasting presence:

  “All the time. ... those moments, the career moments. Of course, I couldn’t get them out of my head. ... But in some ways you think they’ve been watching.”

• [54:32] On what his father’s approval would mean:

  “Hopefully the thing that would be most important is he’d say, ‘You did good. You’re a good man.’ That would mean the most."

Notable Quotes & Memorable Moments

• [05:54] “You never forget your first laugh, your first applause ... it just drove me and it still does to this day.” —Billy Crystal
• [13:06] “I couldn’t shake him ... I was so immersed in Eli and fearless in what I would do.” —Billy Crystal (on acting in “Before”)
• [39:44] “What if Robert Klein was in town? ... Maybe none of it happens.” —Billy Crystal (on fate)
• [48:32] “I said, then we’ll cut to a woman, an older woman, and she’ll say, ‘I’ll have what she’s having.’ And that’s how it happened.” —Billy Crystal (on the famous line)
• [52:47] “You turn it into something that’s art ... And for that, 700 Sundays ... was so important to me. And that it was important to audiences too, still makes me glow.” —Billy Crystal

Important Timestamps

| Timestamp | Segment | Topic | |---|---|---| | 03:49 | Opening | Why the Jack Crystal Theater is meaningful to Billy | | 07:58 | Career shift | “Before” – Billy’s dramatic TV series at Apple | | 13:06 | Acting method | Staying immersed in the character of Eli Adler | | 16:28 | Casting | Finding young actor Jacoby Jupe for “Before” | | 23:22 | Formative years | Early talent, jazz, high school performing | | 26:28 | Studying | Learning film from Martin Scorsese at NYU | | 29:20 | Family | Janice’s role in Billy’s breakthrough | | 33:54 | Muhammad Ali | The connection and evolving friendship | | 44:41 | Film legacy | “When Harry Met Sally” and its enduring relevance | | 49:32 | “700 Sundays” | Storytelling as a means to process loss | | 53:38 | Reflection | What Billy hopes his father would think |

Themes & Tone

• Nostalgic, candid, and warm, the conversation weaves between humor and poignant reflection—mirror to both Billy Crystal’s comedy and his life journey.
• The power of early family and community influence, Jewish heritage, and fate.
• Professional perseverance, artistic risk, and friendship are recurring motifs.
• The importance of legacy and making art from the joys and losses of life.

For listeners:
This episode is a moving portrait of Billy Crystal’s life and craft—from family and humble jazz roots, to Emmy, Tony, and Kennedy Center honors, to late-career reinvention. With honesty and self-deprecating humor, he and Willie Geist excavate the history behind the performances, the serendipity of big breaks, and the enduring impact of storytelling—on both performer and audience.