Living The Red Life
Harold Perrineau: The Struggles They Don’t Tell You About in Acting
Thu, 22 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 – Early Struggles and Theater Roots04:46 – Being Typecast and Breaking Out07:11 – Acting in 'Oz' and Its Challenges09:32 – Playing Mercutio in ‘Romeo + Juliet’12:07 – Working with Leonardo DiCaprio & Baz Luhrmann14:29 – Landing Iconic Roles and Staying Grounded16:59 – The Power of Luck in an Acting Career19:03 – Meeting Morgan Freeman & Denzel Washington21:00 – Advice for Aspiring Entrepreneurs23:17 – ‘FROM’ and Unexpected SuccessConnect with Rudy Mawer:LinkedInInstagramFacebookTwitter
Chapter 1: What early struggles did Harold Perrineau face in his acting career?
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.
Chapter 2: How did Harold Perrineau break out of typecasting?
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.
Chapter 3: What challenges did Harold face while acting in 'Oz'?
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.
Chapter 4: What was it like for Harold to play Mercutio in ‘Romeo + Juliet’?
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,
Chapter 5: How did working with Leonardo DiCaprio and Baz Luhrmann shape Harold's career?
My name is Rudy Moore, host of Living the Red Life podcast, and I'm here to change the way you see your life in your earpiece every single week. If you're ready to start living the red life, ditch the blue pill, take the red pill, join me in Wonderland and change your life. 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 things. favorite show. Good, good. My wife's very scared of it. We watch it late at night and lots of awesome movies.
Chapter 6: What role does luck play in an acting career according to Harold?
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? Those are hot. I like them.
Chapter 7: What inspiring advice does Harold have for aspiring entrepreneurs?
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, and 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. Yeah, damn.
Those are the ones I like, though.
Chapter 8: What can we expect from Harold's recent show, 'FROM'?
I'll get you a pair next time we see each other.
All right. 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 at this point, but 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 a couple of minutes. It's really easy to summarize. I come from these projects in Brooklyn called Cypress Hills. I do that all the time. Cypress Hills is in East New York. And nobody in my neighborhood was an actor or anything like that. And it's been a long journey from Cypress Hills to the Matrix Revolutions and Reloaded and all of those things. And
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 and 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?
Exactly right.
Do you think about that now?
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