The Living Your Legacy Podcast
The Untold Journey of Harold Perrineau – From Dancer to TV Icon
19 May 2025
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.CHAPTERS02:12 – Becoming a Legacy Maker: Harold’s Journey Begins04:46 – From Rejection to Recognition in Hollywood07:11 – The Grit Behind ‘Oz’ and Gritty Roles09:32 – Shakespeare, Mercutio & Changing the Narrative12:07 – Working with Icons: Leo, Baz & the Breakthrough14:29 – How Staying Weird Opened Doors16:59 – Building Legacy: Hard Work Meets Luck19:03 – When Morgan Freeman and Denzel Recognize You21:00 – Acting Like an Entrepreneur: Ownership in the Arts23:17 – Why 'FROM' Is a Legacy Project of Its OwnCONNECT WITH HAROLDIG - HaroldPerrineau
Full Episode
Welcome to a very special episode. We have someone that I've been a big fan of for many years, and I'm sure you have too.
You've probably seen him on the big screen. Thank you. Thank you for having me. Harold Perrineau is a true legend in film and television, known for iconic roles in Lost... Right out of my hands. They took my son and... Oz... We wear our game face all day. The Matrix trilogy, and so much more.
he's doing this superman thing beyond acting he stepped into entrepreneurship as a co-founder of sable bourbon a premium whiskey brand created alongside longtime friends and co-stars i don't want to just sit through the rest of my life you know what i mean and i don't want to just keep doing things that i know how to do because then i'll be bored and so yeah i like to try new stuff and just get out there and see it that's why success
isn't so straight line. And it's not like, I'm so desperate to be successful. It's just like, I just want to keep learning stuff.
And your life story and the lessons, I know it's going to impact thousands or tens of thousands of people. That's why we do what we do here.
Exactly right.
What would you give to tips to entrepreneurs starting out that look up to you? They've watched you in Lost and all these movies.
I would say to you, and I say it directly,
It spans the globe like a super high school internet. Today, Apple is going to reinvent the fun. It's not over until I win. The Living Your Legacy podcast for those who live to leave a legacy. That's extraordinary. The impossible. Oh, that is sensational. Chicago was the lead. Usain Bolt is the fastest man on the planet. You can live your dream.
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