The Living Your Legacy Podcast
The Untold Journey of Harold Perrineau – From Dancer to TV Icon
Mon, 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
Chapter 1: What is Harold Perrineau's journey in the entertainment industry?
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.
Chapter 2: How did Harold go from rejection to recognition in Hollywood?
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
Chapter 3: What challenges did Harold face while working on 'Oz'?
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.
Chapter 4: How is Shakespeare and Mercutio relevant to Harold's career?
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.
Chapter 5: What was it like working with iconic figures like Baz Luhrmann and Leonardo DiCaprio?
Exactly right.
Chapter 6: How has being unique helped Harold in his career?
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.
Chapter 7: What role does hard work and luck play in building a legacy?
I would say to you, and I say it directly,
Chapter 8: How did recognition from Morgan Freeman and Denzel Washington impact Harold?
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.
Chapter 9: What entrepreneurial ventures is Harold involved in?
What's up, everyone? 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. Harold sat with me today. Legendary from Lost From, which is one of my new favorite shows. Good, good. My wife's very scared of it. We watch it late at night. And lots of awesome movies.
Chapter 10: Why is the show 'FROM' significant for Harold's career?
And we're going to talk today about, you know, the entertainment, acting, you know, career and industry and how it links to success and failure and resilience and what we go for as entrepreneurs. And so excited for this. So welcome. Thank you.
Thank you for having me. And listen, before we even start, what I really want to know is, where'd you get those red Nikes from? Yeah.
Those are hot. I like them. So the funny thing about the red, right, is my personal brand, so all I wear is red. Okay. And when you can only wear red, that's all I wear, you find a lot of fascinating red things when you're always Googling and, like, it's a never-ending search for, like, crazy red things.
When we were about to start, I was looking down and I was like, damn, I like those. I'll get you a pair next time we see each other. Right on. But let's talk about what you want to talk about first.
Okay. So, I mean, let's just start with your, I know we've been filming today and I know your life story very well. Let's summarize it for people listening. Like I love that. Like, you know, it really is that like from, from nothing that, that story of just believing in yourself and defining the odds and just going for it.
And one thing that I think people don't see in acting and Hollywood is it's not a straight line, just like business. It's almost identical. Can you just summarize that journey for us?
yeah no it's it's uh it's really easy to summarize i come from uh uh uh these projects in brooklyn called uh cypress hills i do that all the time cypress hills is in east new york and um you know nobody in my neighborhood was an actor or anything like that and uh and it's been a long journey from you know cypress hills to the matrix revolutions and reloaded and all those things and uh
And so, yeah, those things are filled with so many ups and downs and like learning new skills for a long time. I was a dancer. You know, I wrote some songs. So I was in the music part of it for a while. Always wanted to be an actor and had to keep struggling to do that. And so there are lots of twists and turns and pivots and in order to get to a place where you might call success.
Well, the funny thing about success, and we'll come back to it, but it's like an ever-moving target, right? Because it's like, in a lot of people's eyes, I think both of us sat here have had a lot of success, right? But for us, it's still like, we're like, what's next?
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