Sunday Sitdown with Willie Geist: Sylvester Stallone on "Tulsa King," "Rocky," and a Lifetime of Fighting Back

Episode Date: September 7, 2025
Guest: Sylvester Stallone
Host: Willie Geist

Overview

In this captivating episode, Willie Geist sits down with Sylvester Stallone at Stallone’s home in the Hamptons for an in-depth, unfiltered conversation. They discuss Stallone’s success with the hit series “Tulsa King,” the endurance of “Rocky” and its roots, his lifelong fight against adversity, lessons from a tumultuous youth, the art of writing and acting, the costs of fame, and his impending Kennedy Center Honors. Warm, witty, and at times vulnerable, Stallone reflects on where he's been, what he's learned, and what keeps him pushing forward.

Key Discussion Points & Insights

1. "Tulsa King" and the Art of Reinvention

Timestamp: 04:03 – 10:00

• Success of "Tulsa King":
  • Willie congratulates Stallone on “Tulsa King” season three and its status as the number one hit on Paramount+.
  • Stallone explains Dwight’s (his character) growth: from making money to branching into liquor distributorship—“if this works, we’re talking hundreds of millions of dollars” (04:27).

“He’s into something where he could become really formidable in the world of business, but that also comes with a lot of enemies and a lot of jealousy.”
—Sylvester Stallone (04:27)

• Fish-out-of-water Premise:
  • Stallone admires how show creator Taylor Sheridan puts a 75-year-old mobster in Tulsa:

“You have to start your life at 75 from scratch. That’s interesting.”
—Sylvester Stallone (05:36)

• On Working with Taylor Sheridan:
  • Cites their long history (“I wanted him actually to work with me on Rambo 4” [07:41]).
  • Sheridan’s style: he focuses on "Middle Earth" America—relatable, Americana storytelling with no elitism—bringing back “the Western everyone forgot” (08:34–09:48).
  • On casting older stars like Stallone, Costner, or Ford: “It wasn’t as though he took me and says, okay, you’re gonna be a librarian. That’s not gonna work. I think you’re kind of a thug. So they’re perfect casting.” (09:57)

2. Writing, Creativity, and Artistic Pain

Timestamp: 10:16 – 15:55

• On Writing for "Tulsa King" and More:
  • Writes for the show, including the season premiere.
  • Humorously describes the pain of writing:

“Every writer looks like Igor. … You see that little creepy guy with, you know, his forehead’s back here, thick glasses, unshaven… That’s the writer.”
—Sylvester Stallone (10:27)

• Writing is “torture,” yet he can’t stop: “It just keeps pulling you back in…” (12:38)
• Dialogue as a Superpower:
  • “My writing was brought before the class, like, this is how not to write. … But I understood dialogue. Yeah, I really understood that.” (13:33)
• On Artists Wearing Multiple Hats:
  • Encourages performers to produce, write, and direct.
  • “Show me a happy director, and I’ll show you a liar. … It’s like the end of your private life.” (14:38)
  • “My profession sucks, folks. Okay? You’re guaranteed 96% unemployment. Welcome.” (15:55)

3. Working with Stars and Family on "Tulsa King"

Timestamp: 17:51 – 21:42

• On Samuel L. Jackson joining the Series:
  • “As soon as he comes on… tremendous elevation. … It’s like football; you have a great quarterback but then you get the best receiver in the world.” (17:58)
• On His Daughter Acting Alongside Him:
  • “Being a parent, you realize you’re the dumbest person in your life… But the guy with a leaf blower tells us... he makes sense.” (19:26)
  • Daughter’s Stallone impressions from childhood: “She’s doing impressions of me, which is pretty frightening at about 4 years old… Am I that bad? Worse.” (20:17)
• On Empty Nest and Family:
  • “When the kids leave, here’s the key to happiness. Buy kavapoos… They’re now our adopted hairy children.” (21:15)

4. The Tumultuous Road to "Rocky"

Timestamp: 21:51 – 34:51

• Difficult Upbringing & How It Fueled Him:
  • Working on a memoir with Harper Collins about “all this confusion and chaos and turmoil” preparing him for the tough road to “Rocky”.

“My life... reads like a bad novel. So I made it a novel that I try to rationalize... Maybe all this hardship... prepared me for what was coming, which is an unbelievable, difficult voyage to get this film made when you are nobody.”
—Sylvester Stallone (22:18)

• Childhood Obsessions with Fantasy and Isolation:
  • “I didn’t have friends... What appealed to me was true fantasy.”
  • Recalls dressing as Superboy: “They actually put like a dunce cap... but I almost enjoyed it. … I was a classroom dunce, but I just didn’t fit in. And that sense of being alone is the key to my success. I was able to be alone.” (25:28)
• Monastic Devotion to Craft:
  • Describes total isolation and self-abuse in New York: “...four and a half years, I never went to one restaurant… just, you know, so the more you hit it, the more you grind, the more you sacrifice… That’s the only way you can actually say on your deathbed at the end, okay, I didn’t make it, but, God, I gave it everything I had.” (29:19)
• Genesis of "Rocky":
  • Motivated by being typecast as a thug/outlier, he created an underdog nice-guy boxer.

“But he has goldfish, he has turtles. He’s a nice guy. … Poor guy. He just was terrible at being mean.” (34:51)

• “Boxing… it’s very relatable because everyone can sort of relate to that, even if they’re blue collar, white collar people.”
• “He realizes he’s a loser. He accepts it. I’m a bum. ... I wrote it at the end for him to lose… everyone has a different standard…” (38:09)

5. Standing His Ground: Refusing to Sell Out Rocky

Timestamp: 39:57 – 43:31

• On Turning Down Money to Sell "Rocky":
  • Studios offered large sums to buy the script if they could cast a star; Stallone refused, determined to star in it himself.

“I had almost mastered the art of poverty. I knew what it was like. … If you get rid of this... you will be the most bitter human being because the entire thing was not about selling out. It was about integrity.”
—Sylvester Stallone (40:19)

• Legacy: Inspiring Damon & Affleck and Others:
  • Matt Damon and Ben Affleck used “Stallone, Stallone” as a rallying cry when fighting to star in “Good Will Hunting”:

“That’s their rallying cry. Was Stallone and just look at each other. Stallone.” (43:23)

• Stallone reflects: “But more importantly, I realized I was never going to make it as an actor... that’s why I pivoted to writing. So that failure was really an opportunity of something.” (43:31)
• Self-learning from the Greats:
  • “I read ... original writings from Longfellow and Emerson and Cotton Mather and Poe … I’m in a room with 52 million books. So what is your excuse?” (44:04)

6. Fame, Criticism, and the Wounds of Childhood

Timestamp: 45:08 – 49:40

• Sudden Stardom and Fallout:
  • “It was a catastrophic change... there was a sense of I told you so, and... I totally understand it when I go back and I read... this was petulance. … It was me getting back at my, you know, childhood, saying, I told you so. … It took me a while, 70 years, to figure that out…” (45:41)
• The Pain of Criticism:
  • Shares barbs from critics: “When you read your first review and he goes, Stallone’s career is stranger than crib death. … The newest actor to crawl from underneath Brando’s trench coat.” (46:37)
  • “You can get all these accolades, but one biting review... and I go, what is that? … They hurt. They're bullets.” (48:20)
  • Relates it to social media: “You post something, you have a thousand flattering comments, and you find the one, ‘You suck’” — focus on the negative (48:29)
• Why Actors Crave Approval:
  • “Most actors... are not complete individuals. … The acting fills that void… I feel more at home sometimes playing someone else. … you’re getting adulation. And then one bastard rains on your parade. It’s devastating.” (49:32)

7. Recognition & Legacy: The Kennedy Center Honors

Timestamp: 50:06 – 52:17

• Receiving the Kennedy Center Honors:
  • “I thought it was an impersonator... I thought that was never gonna happen. … I was startled, really was.” (50:10)
• On Artistic Legacy:
  • Doesn’t dwell on past achievements, always craves what's next:

“That’s why I said an artist dies twice, and the second time’s the easy one. When you have this, nobody wants you anymore. That’s devastating.” (50:59)

• Expresses that “the next generation has to be defined by who they like... That’s progress. Sad but true.” (51:57)
• Self-effacing humor: “I’m a vowel. ... A, E, I, O, U, and sometimes Y. That’s me. I’m just a vowel.” (52:08)

Notable Quotes

• On Writing:

  “I look at writing and I want to eat the script. … When you’re on the case, it’s 24/7, you’re laying in bed, you get up, where’s my pencil? … It’s a terrible thing.”
  —Sylvester Stallone (11:21)

• On Being Perceived vs. Inner Truth:

  “I’m always that guy, but I don’t see myself that way. I want… I’m like Ferdinand the Bull. ... That’s the way you perceive. So ... I’m going to write a story about that kind of guy. But he has goldfish, he has turtles. He’s a nice guy.”
  —Sylvester Stallone (34:51)

• On the Roots of Rocky:

  “He realizes he’s a loser. He accepts it. I’m a bum… When I wrote it at the end for him to lose because he won. ... Rocky knew he’ll never be Apollo Creed. So I just want to be standing. ... At the end of their life, saying, I did the best damn thing I could. And that’s what the metaphor was.”
  —Sylvester Stallone (38:09)

• On Rejection:

  “We are in the rejection business. Know that. ... I became like marble. ... Because I expected rejection. Acceptance was like, what?”
  —Sylvester Stallone (31:06)

• On Fame’s Dark Side:

  "You can get all these accolades, but one biting review or slanderous statement... they hurt. They're bullets."
  —Sylvester Stallone (48:20)

• On Legacy and Aging:

  “That’s why I said an artist dies twice, and the second time’s the easy one. When you have this, nobody wants you anymore. That’s devastating. … Just when you have all this wealth of living life. Next.”
  —Sylvester Stallone (51:00)

Memorable Moments

• His daughter lampooning his “Stallone-ness” at age 4 [20:17]
• The Superboy costume story and wearing a dunce cap in school [25:28]
• Referring to himself and other artists as “a vowel”—A, E, I, O, U, and sometimes Y [52:08]

Useful Timestamps

• 04:03 “Tulsa King” Explained
• 06:31 Fish out of water/premise
• 10:16 Writing for the show and writing process
• 17:51 Sam Jackson’s appearance; working with his daughter
• 21:51 Early life and impact of struggle
• 25:28 Superboy/dunce cap story
• 34:51 Genesis of “Rocky”
• 40:19 Refusing to sell “Rocky” without starring in it
• 43:23 How Matt Damon & Ben Affleck used “Stallone” as inspiration
• 45:41 The personal cost and disorientation of sudden fame
• 48:20 Criticism and thin skin
• 50:10 Kennedy Center Honors and reflecting on legacy
• 52:08 "I'm a vowel..."

Conclusion

This lengthy, honest conversation with Sylvester Stallone uncovers not just the public fighter, underdog, and action star—but a driven, often vulnerable artist who endures through loneliness, criticism, and reinvention. Whether it’s writing, acting, or just being dad, Stallone’s story remains a testament to grit, self-belief, and never letting your underdog narrative go unwritten by someone else.