Harold Perrineau, acclaimed actor best known for roles in Lost, Oz, and Romeo + Juliet, joins the show for an inspiring and deeply personal conversation. From humble beginnings and being misunderstood as a “weird dancer” to becoming a staple in some of television and film’s most groundbreaking projects, Harold opens up about the grit, passion, and occasional luck that shaped his path. He reflects on his time in theater, challenges in breaking out of typecasting, and what it was like to work with legendary talents like Baz Luhrmann, Leonardo DiCaprio, and Anthony Hopkins.

Throughout the interview, Harold dives into his evolution not just as an actor, but as an entrepreneur and creator. He shares unforgettable moments—like being recognized by Morgan Freeman and getting praise from Denzel Washington—and how they affirmed his journey. He also discusses his recent hit show FROM, what’s next for his production projects, and drops empowering advice for anyone building a career or business from the ground up: stay engaged, stay interested, and never stop building. It’s a masterclass in passion and perseverance.

CHAPTERS

02:12 – Early Struggles and Theater Roots

04:46 – Being Typecast and Breaking Out

07:11 – Acting in 'Oz' and Its Challenges

09:32 – Playing Mercutio in ‘Romeo + Juliet’

12:07 – Working with Leonardo DiCaprio & Baz Luhrmann

14:29 – Landing Iconic Roles and Staying Grounded

16:59 – The Power of Luck in an Acting Career

19:03 – Meeting Morgan Freeman & Denzel Washington

21:00 – Advice for Aspiring Entrepreneurs

23:17 – ‘FROM’ and Unexpected Success

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Harold Perrineau: The Struggles They Don’t Tell You About in Acting