Living The Red Life - Harold Perrineau: The Struggles They Don’t Tell You About in Acting

Episode Date: May 22, 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

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 were at a game place all day. The Matrix trilogy, and so much more. He's doing the 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 Lofts and all these movies. I would say to you, and I would say it directly. My name's Rudy Moore, host of Living the Red Life podcast. 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 favorite shows. Good, good. My wife's very scared of it and we watch it late at night. And lots of awesome movies. And we're gonna talk today about, you know, the entertainment acting 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 wanna know is, where'd you get those red Nikes from? Those are hot. I like them. So the thing about the red, right, is my personal brand.

So all I wear is red. OK. And and when you can only wear red, that's all I wear. You find a lot of fascinating red things. And you always Google and and like, it's a never ending search for like crazy red things. Yeah, we were about to start for like crazy red things. Yeah. We were about to start looking down. Damn.

I like that. I'll get you a pen next time we see each other. Okay. But let's talk about what you want to talk about. 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 Like I love that, like, you know, it really is that,

like from nothing, that story of just believing in yourself and defining the odds and just going for it. And one thing that I mean, people don't see in acting and Hollywood is it's not a straight line, just like business, it's almost identical, you know? Can you just summarize that journey for a couple minutes? Yeah, no, 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 those things. 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. I wrote some songs and so I was in 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? Cause 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? All, we're like, what's next? Exactly right. Do you think about that now? All the time. I wish I could stop thinking about that. Somebody asked me the other day, they said,

oh, when did you realize that you made it? I was like, I don't know what you're talking about. I made it. I'm still on the wheel. And it's not like I haven't done well, right? We've done well, but still there's always another new step to keep you interested. I think that's the successful trade of like,

you know, I work with a ton of pro athletes, as you know, and get to meet so many amazing people. And I love what I do because of that. And we all have this like, we're all connected somehow with this like, I say I'm a little delusional, right? And you said you still think you're normal, even though your family tell you you're not.

You haven't cut and done you're not yet. But we have to have this level of like, just we're out the box. We're not a normal person. We keep striving for more. We, and we don't settle. Yeah, I'm really glad that when I started acting, I didn't know what it took

because I would have never done it. Like, I'm really glad that at this point I was just like, I just believe I can. And the truth was I probably shouldn't, but I did believe it. And so then you just keep going and keep working it out and keep working it out. But there is a real delusion.

There's a real like, no, no, no, no, no, yeah, yeah, yeah. No, I know I'm weird. I'm weird looking and, but I'm still gonna, I'm gonna be an actor. And then here I am. So it's pretty cool. It's the same in business. Cause it's like when you start, everything doesn't work.

You have no money and you think, oh yeah. When I have like, I have a hundred employees roughly now. And you're like, oh yeah. When you're at that level, everything's good. And it's like, no, you have like a million dollars a month in expenses. People try and, you know, employees will trip over something and try and sue you for no reason.

You know, people you've never met will try and sue you. And then everyone else will try and copy you. That's really wild. I mean, that's wild. So many things are really the same as like an actor, like, you know what I mean? Like I have to take out insurance in my house because if I have a party and somebody does a thing,

they could try to sue you, which has actually happened. So it's crazy, I didn't realize so many things were, until we were talking today, so many things were so similar with entrepreneurs and I'm glad you're telling me about this. You know, I just started a bourbon business, which we talked about. And so now I got things to look forward to.

The ups and downs of bourbon. You're doing it all over again. Yeah, exactly. And I'm kinda doing it in the reverse. I just started, you know, getting into a company. Media TV, yeah, you're doing it all over. Yeah I just started you know, get a TV. Yeah TV. So right. I was telling you earlier, you know, I I struggle to memorize free lines Right, right So I'm like the beginner over there, you know, and but that's also I think something interesting like we always like to challenge ourselves You're challenging yourself constantly. I do. You know, why is that?

I do like, because it's always like, it's really interesting. Every challenge is something new and interesting. You know what I mean? I don't, I don't want to be bored. I don't want to sit, 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 wanna keep learning stuff. You know, this funny ups and downs of success, very similar in my entrepreneur journey and entrepreneurs I see in the acting side. And I remember one thing that you were talking about earlier

was being the tree in the back of a dance performance. Exactly, yeah. I want to talk now about the summary of your success in this industry, right? You're highly respected, very well known in some of the biggest shows and movies on the planet. How does it feel going from the tree in the back, you're just wiggling around,

to now you're leading this amazing role in From, being in Lost in Matrix 28 weeks later. How does that feel to reflect on that? It's really interesting to think back in the whole journey, to think back on the time when you're like, damn, I'm just gonna be stuck in the Bronx forever. So I used to live in the Bronx for a little while

and to actually be here today, like leading the show on prom and stuff like that. And it just makes me, you know, it makes me really understand like the power of belief. Like I can only say like, you just really have to believe like I'm fully living proof that that's how you move forward. You have to pivot.

You have to do all these things. You have to, and you have to be tree number three. Like you actually have to go and do that because that keeps inspiring you to like not have to do it again. You know what I mean? You'll be tree number three and the next time you're gonna be tree number one.

And then the next time you're gonna be the dude. So it's a, it really, when I think back about it, man, it's been a long journey. And of course, when we look back, it's been really, it's been really interesting and cool, but at the time it was all felt really, felt really tricky and like, oh, it's gonna take forever.

And, but now here we are. We're like, I'm doing stuff that I love. And this is still a hard time. This is still hard We're like, I'm doing stuff that I love. And this is still a hard time. This is still a hard time. But I really am doing things that I love and I can't, I couldn't be happier. I've been a really lucky dude. You had this idea of who you wanted to become.

Right. And it was very different to all your friends and your environment you were born in. Right, so talk about that. And also I'd love you to talk about if someone's in an environment right now and they're the odd one out. Like I was in England. Were you the odd one out in England? Yeah I was an entrepreneur, very different obsessed with money and yeah and you you very similar to me you were totally

different like you were different. Yeah yeah. Talk about that. Yeah no when I was in when I grew up in Brooklyn in uh in Cypress Hills I was just I was just the cat that wasn't like, I couldn't play any of the sports. I wasn't that cool to hang out with. People used to do the dozens. Yo mama is so stupid. My yo mama jokes were the worst jokes you have ever heard. Like, you know what I mean?

And anything that I could do wasn't really cool. Like I was really good at math, that wasn't cool. And then I became a dancer and that wasn't so cool. But like a ballet dancer, there's lots of people who can dance, but I was like a ballet dancer. And so all that stuff was really, really, it was really tricky to see yourself, to see yourself succeeding, even though where the environment where you are, you're completely failing, because it's just not where you belong. And you really just have to go like, you know, this is not for me, man. I'm not knocking anybody else. It's just, this is not for me. I don't belong here. I can't hustle drugs. I just can't. I don't know how to do it. Do you know what I mean? I don't have that kind of, I'm not that brave.

I'm not so, I'm not interested in it. And so what I want to do is I want to be, I want to go do Swan Lake. I really, really do. Like I want to learn how to dance to Tchaikovsky. I really, really do. I do want to go read like, you know, the great plays by Arthur Miller and, you know, and do those on Broadway. That's what I want to do. I want to do Shakespeare.

And so it's been really tricky to be that goofy guy, but like just step into it I'll just be like alright, then I'm just gonna I just got to be that goofy guy and I'm just gonna have to see where that goes and It's taking me pretty far and if someone's listening they feel that the yeah Absolutely, and that's one of the things again. We talked about this earlier. We talked about representation, right? It's really important to see different types of people who do all these things, to see women who are entrepreneurs and men who are, who are dancers, bisexual people who don't have to talk about their sexuality at

all, but really succeed in whatever field they're in. Representation is so important because if somebody is out there that feels like they're alone, they're the only person who looks like them, is like them, thinks like them. You know what I mean? You have to know that you're not the only person like that.

And that you need to see people who felt the same way and actually have been able to succeed in their own journey. And following up from that, what would you say to someone that they're stuck in the environment? Because I meet a lot of entrepreneurs and people trying to get started, but everyone says they shouldn't quit their job, they shouldn't become an entrepreneur, their idea is stupid, they're going to fail. What would you say to someone? Listen, at the end of the day, I'd say what I've been saying the whole time, you really just have to believe it. I don't know if you should quit your job.

I don't know, like, I had a lot of jobs that I didn't quit and I just kept going. I met everybody that I could who was like doing plays and I would do all these readings, like a place for no money at all. And then I would go to my bartending job or my, you know, my waiting job and then come back. And I just did everything I could to stretch myself,

to be in the place where I wanted to be. I started treating myself as if I was already there. Like if I had to do a bartending gig, I'd do my bartending gig and it's like, oh, hold on, I gotta go meet this director. And it really is just a friend of mine who's directing a little play and that's all good, but that's really the place I wanna be.

Like you have to try to put yourself in those places where you will find your community. Every one of us will find the community of people that vibe with us and you'll be able to really sail when you find those people. Well, and I admire that about you. You've got that hustle, right? And you always had that hustle.

And then we were just talking now, you still got that hustle. You know, you're about to leave, you know, amazing California, Hollywood, right? You got your family here, you're set here. You go into Nova Scotia, which isn't quite the same. It's far away, man. You're going to be there for many, many months filming from. Like, you don't have to probably go and do that. Right, right.

But I do because I'm still hustling, right? I'm still trying to make great art. I'm still trying to make a name for myself, even as it were. And, you know, my daughter just turned 12, and I'm just going to miss this part of her 12, which is going to be really, I'm going to try to do everything I can to see her as much as I can. But, you know, I'm sacrificing that thing because, you know, I have this desire.

I have this desire to succeed. My success isn't more important than my daughter, but I want her to see that, you know, you have to be able to work hard and sometimes you have to do a little sacrificing right now to get what you want eventually, you know what you have to be able to work hard and sometimes you have to do a little sacrificing right now to get what you want eventually. Do you know what I mean? So how is that, you know, on the family side, like,

you know, you're a role model, right? Like I think it's so important too, because especially, you know, I'm not a parent, but I have a lot of friends where their kids, you know, their parents are worth 10, 20 million, right? Or the, you know, you're obviously a successful actor. How important do you think that is for them to see you hustling still

in that role model-like figure? Like, I think it's, look, I think it's important to raise great human beings, right? And so being a great human being means you're active in your own life as well. And so I like them to see me do things that I succeed at And I think that being a human being means you're active in your own life as well. And so I like them to see me do things that I succeed at or that I work really hard for.

And because they're not going to see the part that's really hard, which is parenting. Parenting is really hard. They're not going to see that part, but they're going to see the other things that I do and realize that even within that, I still try to incorporate them as well. And I think it's gonna help them be really great, rounded human beings and find their own passions and figure out like, oh, my dad, he used to work really hard.

I remember those times he would go away. So, you know, I might not have to, I might not be able to be with my friends tonight, but I do want to go and do this thing because it's really gonna serve me in whatever it is I'm looking for. And so hopefully they'll see those things happening with me and that'll inspire them in some way. I hope.

I hope. And just last couple of questions we come to wrap up. I'd love to reflect on some of your biggest highlights, right? So you know, you're in obviously Lost, Now, now from Romeo and Juliet, you know, Matrix. Was there any one moment in all of those or a different show or movie where you got the call or you got the role and you're like, you reflected and you're like, wow, that's crazy?

I got to say that, you know, in my career, I've had a lot, I've been really successful. Lucky is what I mean, not just successful, but like, there are a lot of actors and there are a lot of great actors. And like not only working hard, but it takes a little bit of luck, you know what I mean? And luck is almost where you make it.

You put yourself in the position, you have to be lucky. So, but I do remember when I got William Shakespeare's Romeo and Juliet and I had the dreads and I was just, you know, and I was like this dancer who was weird and wacky, and I didn't think I had a shot in hell to get it, but I kept going back and going back and going back, and Baz was like, let's try this, let's try this, and then I wound up being there, and I remember when I got it, I was just like, oh snap, I'm about to do Shakespeare, Shakespeare, with, you know, some of the greatest actors on the planet and this amazing young director, Baz Luhrmann. And, and it was one of those, one of those

times when I was just like, this is wild. Like, this is wild. We shot in Mexico City and it was, it was really, really amazing. It felt like, yeah, yeah, it felt really good to have to do that. That's a great one. And I also know you talk about another one where like, yeah, some of really good to have to do that. That's a great one. And I also know you talk about another one where, like, some of the maybe actors you looked up to, or some of the big famous ones along, you know,

that you've seen in other big movies, they come up to you on red carpet. Yeah, yeah. I had done this movie also. I did this movie called The Edge. And it's me, and it was Alec Baldwin and Anthony Hopkins, which is already mind blowing. Like, it's mind blowing, it's crazy.

And we go to the premiere and we walk out of premiere and somebody goes, young man, that bear ate you up. And I look up to see who it is and it's Morgan Freeman. And I stop. I'm just like, I wish to bring you back. Like, I can barely say a word. Like, you know, it's crazy. Or like, I did this play,

and Denzel Washington came backstage, he's like, man, you a tough dude. And I was like, oh, Scott, that's Denzel Washington. You know, like, these are people who I've looked up to my whole career, and sort of tried to emulate part of my career. Like, they're amazing, amazing artists, and they work really hard, and I've tried to emulate part of my career. Like they're amazing, amazing artists and they work really hard and I've tried to emulate them.

And it's just such a wild thing. And when they come up and they're talking to me, it's crazy, it's crazy. I always love, I ask these questions because I personally like, I love those, you know, and I always say it's the ones that you go home and like tell your wife about. Yeah.

What's funny with my wife is she's like busy in the kitchen and I'll tell her this crazy story. Right. When Denzel came up to you or whatever. And she's like, oh yes, it's great baby. I don't know if you ever get that. I get that all the time. Like, oh yeah, it's really cool.

My wife isn't impressed by mostly anything. The only thing my wife wants to do and I've never been able to do it is meet Larry Bird. That's her whole, like her whole, I could tell her I met anybody. I could say Nelson Mandela came back and was talking to me, and she'd be like, oh, oh, that's interesting.

Well, I actually could make that intro. You could make it into Larry Bird? All right, man. If you can, we'll do it, because that's all she wants to do. Okay, well there you go. And then she'll be impressed. I thought you were gonna say it was you doing a triathlon. No.

No, that would be me. I'd be like, oh snap, you did that? Yes, I did. We're gonna get you on one of the sprint ones. Okay, okay. I gotta learn to swim though, I really do. So last couple of questions. I always like to ask this at the end of these

sort of interviews is, and I already asked you earlier offline, but someone's listening, they're inspired by your work, right? And all the amazing things you've done, talk to them as an everyday entrepreneur, because you are now, you know, an entrepreneur, right? Yes, right. Especially now with the new business, right? But even I think as an actor, like, you don't get a salary. You have to go out there and like, that's an entrepreneur.

Yeah, every time I get an application, but it's like, who's your employer? Yeah. I am. Yeah. And you write the IRS nice checks over the years too, right? Exactly right. So you're an entrepreneur and you have been for many years.

What would you give to tips to entrepreneurs starting out that look up to you, they've watched you in last and all these movies? Look, I would say to you, and I would say it directly, you have to stay engaged with what you do. Like, things may change or you'll find different pivot points, but you have to stay engaged because you have to stay interested in what you're doing. And the more interested you are,

the more success that you'll have. You'll just have to keep going and your interest will be the thing that drives you to keep going. So stay in there, keep trying, keep working on it, keep building, every time you get someplace else, you want to get another place, all right? So just keep doing it, but you really have to like

enjoy what you're doing. And I don't mean like, I'm laughing and giggling. I mean, you have to really enjoy the process, right? Of creating and building and doing something new all the time. Okay, and one final question, probably the most important one. The most important question, okay.

Everybody listen up, here you go. You've maybe been asked it before too. Where's Walt? Right, okay, so here's the thing. Walt is out here in California. He's a rapper. He's so good. He got off the island. Malcolm Kelly. I love Malcolm Kelly. Malcolm's a rapper. Do you guys stay in touch?

We have seen each other now and again throughout the years. In fact, we did one of these Comic-Cons where we signed James, and I had him there and also the young man who plays my son now. So it was really kind of dope to have them both there, and we just took pictures together. So I see them once in a while. I follow them on social media. I'm really proud of the job that all the Stephanie's doing. And I guess just lastly, tell us about the new, you know,

what you're working on, the big projects right now. I'm going back to the fourth season of From, and that's been a really amazing journey. We've been producing a film called Slay the Dreamer that we finally, I think,

got fully green-lit. My buddy Laurence Fishburne is going to be in, Jeremy Irons, Anthony Hopkins. We've got all these really great talent. That's going to be in, Jeremy Irons, Anthony Hopkins, we've got all these really great talent. That's gonna be in it. We are on tour with Sable Burbin

that I'm doing with my buddy Tay Diggs and Morris Chestnut, Malcolm D. Lee. And we are just in the mix, just like doing a bunch of new things, like putting new projects together. And just like I said, staying creative, it's not easy, but we're just staying in. Yep. I think from, I mean, is that, it's not easy, but we just staying in. Yep.

I think From, I mean, is that blowing up more than you expected? Like I feel it's- From has blown up way more than I expected. It's doing really good. It's doing really, really good. When we first shot the show, you know, we were like, I don't know, this is really scary to me

and it kind of cool, but like, I don't know. I mean, people might like it. And then people just started loving it. And I was like, woof! I thought I was crazy. Which we've talked about already. Yeah. But yeah, lots of people are really digging it now. I was at the doctor's office the other day and the doctor came out of the door to get somebody else.

He goes, Boyd is in the house. I was like, oh, that's weird. It's so good because The hook like a storyline. I'm like, I don't watch TV that often. Like I watch a lot of movies, but it takes a lot to get me in a TV show. Right. But it's like I got to know what where's this going? Yeah, yeah.

Where's this going? And that's the thing we were talking about earlier about connecting with people. We have a lot of characters in that thing, and they connect with different people and different points. So many people can see themselves as Boyd or as Sarah or as Donna or any of the characters, and that's what keeps people coming back. It's not just, oh, this is scary,

because you can see yourself. It's really good writing. Really, really good. I like it. Very good. Well, it's been an honor and a pleasure to have you here today You've been amazing and your life story and the lessons. I know it's gonna impact thousands Tens of thousands of people. That's why we do what we do here. Exactly. So thank you so much for coming in

Everyone go go watch from if you've not already. I promise you is one of the best shows I've seen probably ever Especially in this space. Yeah, yeah, yeah. It's awesome. And thank you so much for your time. Thank you, sir. That's a wrap. Keep working hard, have an impact, build a legacy.

I'll see you guys soon. Take care. Bye!