Don't Wait, Create: A Hilarious Conversation With Dennis Dugan About Taking Creative Risks Seriously

Right for the Role Episode 3 Dennis Dugan
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Veteran director Dennis Dugan joins John Frank Levey to share how embracing life's unexpected turns and maintaining a playful spirit shaped his remarkable journey from actor to billion-dollar comedy director.

Through candid stories spanning his early theater days to directing Adam Sandler films, Dugan reveals how every seeming setback opened new doors. His conversation with Levey explores the delicate balance between taking creative risks and building lasting industry relationships.

In this episode:

  • How getting kicked out of college led Dugan to the Goodman Theater and, ultimately, Los Angeles

  • The fascinating story behind landing Problem Child by literally standing on a studio executive's coffee table during his pitch

  • His unconventional approach to playing Captain Freedom on Hill Street Blues and why staying in character between scenes elevated the performance

  • The full-circle moment of Adam Sandler hiring him to direct Happy Gilmore because Dugan had championed him years earlier

  • Why he's returning to his acting roots after directing films that grossed nearly $2 billion

  • The power of creating your own opportunities, including writing and performing a one-act play to showcase his acting for agents

  • His philosophy that "if you wait, you'll be a waiter" and why artists need to make things happen

A masterclass in turning setbacks into opportunities and maintaining creative passion across a five-decade career in Hollywood.

TV shows and movies discussed in this conversation:

  • Hill Street Blues (TV)

  • Moonlighting (TV)

  • Hunter (TV)

  • MAS*H (TV)

  • The Mod Squad (TV)

  • The Waltons (TV)

  • Problem Child (Film)

  • Happy Gilmore (Film)

  • Big Daddy (Film)

  • I Now Pronounce You Chuck and Larry (Film)

  • You Don't Mess with the Zohan (Film)

  • Grown Ups 1 & 2 (Films)

  • Just Go with It (Film)

  • Jack and Jill (Film)

  • Estonia, You Fall (stage play)

  • The House of Blue Leaves (stage play)

  • Richie Brockleman (TV)

Connect:

  • Connect with John on IG: @john_frank_levey_

  • Click here to order a signed copy of John's memoir, Right for the Role.

Acknowledgments

Photographer Eusebio Hernandez specializes in “hero shots” — his own artistic spin on headshots. He helped John Frank Levey, who typically hates having his picture taken, feel comfortable enough to get a great shot for his memoir "Right for the Role." Learn more at www.heroshots.la.

The Right for the Role podcast would not have been possible without the generous support of PBS Management, Karen Cease, and the estate of Peg Sweesy.

Many thanks to my producers, Jerod Morris and Trudi Roth of It’s the TruStory

You can also enjoy the Right for the Role podcast on the following platforms:

Spotify

Apple

Amazon Music

Pocket Casts

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