Woody Harrelson is being patient. It’s already early afternoon on a Tuesday and the longtime pot smoker and legal-weed advocate is not high—or, perhaps from his perspective, not high yet. Instead, he’s at a studio in Manhattan with fellow actor Justin Theroux for an Esquire photo shoot, and there are still hours to go in a very long day of press obligations, including an appearance on The Late Show with Stephen Colbert. A clear mind wouldn’t be the worst thing. But he is keeping a joint nearby. First in his pocket, and then on a paper plate, out of the camera frame. Just in case. Ready for the right moment.
Even as he resists temptation, he manages to stay both philosophical and focused on the task at hand. “You never really can prepare for a day like this,” Harrelson says after a few hours. “I guess.” He shrugs, but an amused smile has spread clear across his face. The 61-year-old TV and film icon, with titles like Cheers, White Men Can’t Jump, and True Detective, knows how to soldier through a media blitz. Draped over his black Saint Laurent suit is a brandless fuzzy bath towel. Hotel slippers on his feet.
Harrelson and Theroux, wearing the same black suit and even the same robe just a few feet away, are promoting HBO’s excellent new Watergate comedy, White House Plumbers, out May 1. Directed by David Mandel, who spent years as a producer and showrunner of Veep, the new limited series retells the story of the infamous break-in from an entirely new vantage point: that of the burglars. Harrelson plays the “mastermind” of the operation, E. Howard Hunt, and Theroux portrays his maniacal comrade in paranoia, G. Gordon Liddy. (Paranoia over what? The threat of communism, most generally, and the dire threat of Democratic senator George McGovern being elected president, most illogically.) It is perversely funny. Hunt and Libby pursue what eventually amounts to four separate attempts to break into Democratic National Committee Headquarters. The show scores extra hard from the delight each actor takes in their role and the fact that, holy shit, this really happened.
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After a few different backdrops and a few thousand poses—at one point the photographer asks Harrelson to “relax your mouth” and he goes full slack-jawed, pretending to have fallen asleep—there’s just one shot left. And Harrelson and Theroux are bundling up. It’s a brisk, spring day in New York City, and they will plunge, clothes on, into the nearby hot tub. One problem: The water’s not hot. Not even close. The actors are going to freeze their butts off. “We’ll be glad that we’ve done it,” Theroux says fondly of that time, in the near future, when he’ll be warm again. Harrelson chuckles.
Ideas flow from a variety of set-minders for how to make this dip less uncomfortable. Is there a kettle of hot water nearby? A stack of towels is readied just outside the hot tub. As Theroux accepts a barbecue lighter and his costar submerges, asking, finally, for his joint, the two have everything they need. Theroux, 51, laughs. “Do not inhale!” he shouts comically, out of duty to the duo’s long afternoon still ahead, then sparks the lighter. “Really, do not inhale!” he says again, setting fire to Woody’s joint. Harrelson thanks him by exhaling smoke in Theroux’s face. They both bust out laughing.
It’s just the latest installment of the Woody and Justin buddy act. A few days prior, Esquire spoke with Harrelson and Theroux by Zoom. Harrelson beamed in from his home in Los Angeles, where he resides when he is not in his preferred base of Hawaii, while Theroux, the star of Apple TV+’s The Mosquito Coast and movies such as The Spy Who Dumped Me, joined from New York. Together, we talked about America’s love of a good second act, sleeping naked on airplanes, a certain viral Saturday Night Live monologue, why you won’t be catching Theroux toking up anytime soon, and the fact that both actors were raised by strong single mothers. This conversation has been edited for clarity and length.
ESQ: Justin, how’s your mom doing? The last time you spoke to Esquire you talked about your relationship with her. At the time, she was struggling with Covid isolation and losing her husband.
JT: She’s fabulous. She’s happier than I am. The trait that my mom has, which I admire and I love, is that she’s curious. I can’t walk down the street with her without her pulling on someone’s sleeve and going, “Hey, those are nice shoes.” I don’t chat with people that much. But she zeroes in on people and things and subjects.
ESQ: There was a time after her divorce from your father where she really had to figure out how to support you and your siblings as a single mother. Were you rebellious during that time?
JT: I was resentful that she had made certain choices, but that’s all forgiven now. That was all through the eyes of a six-year-old, a nine-year-old, a twelve-year-old. She used to actually take me to work with her at The Washington Post; she used to stuff me under the desk when I was little. It was that classic, big editorial writers’ room that you see in all the movies with the typewriters, covered in cigarette smoke. I was thinking, Why am I not at my friend’s house or at a soccer game? But at the same time, they’re fabulous memories to look back on, too.
ESQ: Woody, similarly, you were raised by a single mother. This seems like a real through line between your two stories.
WH: [Laughs]
JT: That explains a lot about us, Woody!
ESQ: No, no, I mean this positively. I’ve always enjoyed hearing both of you speak about your moms.
WH: It’s Herculean, what my mom did. The art of being a mother is already an extraordinary thing, but to be a mother who’s working full-time and figuring out how to keep everything going on a relatively small salary—she was a legal secretary, she wasn’t paid much—and all of us had our own eccentricities. You know, I had some problems. I had to be put in a special school that could deal with someone like me. And she managed to make that happen. But I do remember one time reading this letter she wrote to the government about taxes, that what little she had, they wanted. She has a great sense of humor, but you got what a tough, tough situation she was in. I admire her quite a lot.
ESQ: Who was the letter addressed to?
WH: To the U.S. government. One of the last lines was, like, “You’ve taken everything from me. Should I give up one of my chairs? One of my children?” She didn’t say children, but she had a funny term. Anyway, it made me laugh, and it also just made me feel such sympathy.
ESQ: When did some of that anger that, as you say, made you a tough kid at times, start to dissipate?
WH: I still feel anger and rebellion constantly, but now it’s more against the system that exists in our country than it is against a parent. But I started appreciating her more when I was getting towards ten, eleven years old.…Well, I rebelled against this new man she had in her life. I didn’t like him, and it’s too bad, because I really didn’t give him a chance. I took all of his clothes that he had at the house and threw them out on the lawn and then I ran away. I didn’t run that far, so they were able to find me. My aunt talked to me about “You don’t get the sacrifices your mother has made for you.” It was outside of my own little purview. That helped.
ESQ: Your mom created a space where you were allowed to keep the eccentricities that made you you, which has worked out well career-wise. Do you think about that a lot as a dad now?
WH: Absolutely. I want my kids to do whatever is going to make them happy. One works on our farm, and one is going to law school, and then the youngest one wants to be an actress, singer, performer, et cetera. For at least two out of three of those, I’d choose something else, but I love them for wanting to do these things and I’d do anything to support them.
ESQ: Woody, what’s this I’m hearing about you and your good pal Matthew McConaughey now thinking you may be actual brothers?
WH: Well, it’s very much true. I learned from Ma Mac, Matthew’s mother, that she did have a relationship with my father for a relatively short period of time that coincided with the time that his father and mother were on a sabbatical, and with the time of Matthew’s, let’s say, origination. We haven’t done a test, but there are too many times that I think to myself, My God, the similarities! The things he does, the things he says—just the way he is. I’ve felt that for years.
ESQ: Justin, it looks like this is news to you.
JT: It is news to me! And I’m not going to lie and say that I’m ecstatic about this, because I will also posit this theory, that my father was alive at that same time that Woody’s mother was alive, and I can’t prove or deny that they didn’t know each other in some capacity. So this family tree may be growing before our eyes—and there have been many times where I’ve thought the same thing about Woody, that he’s this abusive older brother. Much older brother. The next time he sets a glass down or a fork, I am going to pair it against my own DNA to confirm what I suspect is the truth.
WH: [Laughs]
ESQ: I’ll be giving you the Esquire mailing address and I expect to see the results.
WH: That would make me happy.
ESQ: Woody, you’ve already released one movie this year, Champions. Now you’ve got White House Plumbers, and a handful of more things on the way. Do you always need to be working?
WH: I like the idea of not working, and it might have to do with my peak laziness abilities. But I like to not work. I don’t know why I do work, ever. In terms of working, I might be a middling journeyman, but in terms of not working, I might be the king of that.
ESQ: You have a very long résumé for someone who apparently enjoys not working.
JT: That’s total horseshit!
ESQ: Has to be.
JT: Can I compliment Woody? I’m not doing this because we’re talking near microphones, but I admire his work ethic in that he doesn’t take it seriously the perfect amount. I can be very high-strung. And Woody, who clearly does put in the work—I don’t want to say he is unprepared—he shows up and it’s like a fog rolling onto set and then the work just starts to happen and then he rolls away. On the weekend he’s on a bike ride and then he’s swimming naked in a pond. I’m making shit up, but he can be on a job and at the same moment be having a full life.
ESQ: Justin, there is something oddly appealing to the way you play G. Gordon Liddy. Same could be said for a lot of your characters, from Allie on The Mosquito Coast to Kevin on The Leftovers to Tom in The Girl on the Train. You root for them despite your better judgment.
JT: It’s more fun to watch when someone’s got complications and flaws, even if the character doesn’t think they have those complications and flaws. I think Liddy would say he’s a pretty straightforward family, 1950s, clean-cut man. I don’t think he realized how eccentric he was.
ESQ: I suspect there was a decent part of your career, before people knew that you had this twisted sense of humor, where you were being pushed in the direction of leading-man roles. At what point did you say, “I gotta prove I’m not the guy for that”?
JT: It was just saying no to the right things and yes to the right things. Look, I think I made a bit of a slower road for myself because I never really had a breakout anything. It’s always kind of been like “Oh, there he is.”
ESQ: You came up with Philip Seymour Hoffman, running in the same New York circles. Talk about a master of portraying dark, twisted personalities. Was that part of your initial bond?
JT: We met doing a play together off-Broadway. He had done Scent of a Woman and a small part in Boogie Nights. He used to live on my street, so we’d see each other quite often and he would come over and I’d have a little stack of scripts. And I’d go over to his house, and he’d have a little stack of scripts. He was always getting these offers for “schlubby loser who opens the movie masturbating,” or whatever. I do remember him looking at my scripts going, “I’d like to get some scripts like this.” And I was looking at his schlubby-loser-masturbating pieces thinking, I’d like a script like that. But he was operating at a different level, earlier on, than any of our peer group. He had that capacity to go incredibly deep, and he was wonderful. Shame he’s not here to do it.
ESQ: Something I found emotional in the series is that you see that Hunt really does feel torn between his politics and the fact that by not breaking with the plan, he fails his family. Woody, in your youth you canvassed for the Republican party. Went to the same college as Mike Pence. Did those experiences help you understand the paranoia Hunt was feeling?
WH: I understand it. And there’s still a fear of communism. We still loathe Russia. There’s still all the concern about the liberal agenda. I get how this mentality develops. I’m really, basically, a little bit of both. There are things that the liberals do that I think, What fucking idiots. And then there’s also conservative ideology that strikes me as odd. I consider myself, really, an anarchist.
ESQ: Do you mean that you believe in no government? Or is it that you do believe in government but you don’t like either side?
WH: Well, I’m probably more of a libertarian. I never see government work. It always seems to be working for the people who got you there. It’s businessmen working for bigger businessmen. It’s not businessmen working for their constituents. I think government just usually sucks…am I wrong? Even the social programs, they do it reluctantly, and they’re just always trying to gobble back what they can from the social programs.
ESQ: I don’t think you’re alone in feeling dismayed. You used to do a lot of public activism, but much of that has gone away. Is that related to these feelings?
WH: Yeah. I feel like they weren’t effective. You climb the Golden Gate Bridge to bring attention to the fact that they’re cutting down ancient redwoods in northern California. Well, so what if you succeed? They’ll go cut the trees down somewhere else. What would really succeed is making paper from some alternative product, something from the farmers…which, of course I did that for fifteen years and it just amounted to a huge waste of money. But I do think there are ways to be proactive about changing things, particularly environmental things. It really involves retooling the society and trying to get in where the problem starts as opposed to trying to clean it up later.
JT: See, this is where me and Woody disagree, because I’m always talking about plastic paper. We don’t have to cut down these redwoods. It’s a crazy idea!
WH: [Laughs]
JT: We make water bottles, we recycle them, we make paper. Then we make some more plastic if we need—I’m joking!
ESQ: Justin, listening to Woody talk about feeling disillusioned, do you feel like you get it?
JT: In different ways. I don’t know. It’s weird. God, I don’t consider myself terribly political. Being in the arts, I’ve been to my fair share of protests and made donations and done letter writing, but now I want to stay out of it and just do my work and hopefully that has an impact. I think, especially when it comes to humor or satire, I can do more if I stay in my lane.
WH: But you have, in your family lineage and in your life, spent time in D.C.
JT: I have. One of the reasons why I don’t think there’s some sort of big deep-state conspiracy is that I’ve been able to see that it’s not this big Oz that’s up there controlling things. Living and growing up in D.C., you realize these are just government workers. You pull the curtain back and people are just pulling small levers. They might be pulling them the wrong way and doing things you don’t want them to do, but the FBI is not a big, cool, dark room with tons of computer screens wrapping around the thing. It’s offices with cubicles and pencil holders.
WH: You don’t think the Dulles brothers were up to any kind of nefarious activities?
JT: They built a great airport. We could go down the rabbit hole, but I’m just not impressed. I agree with Woody on a lot of things. We’ve never really gotten into it as far as whether I’m an anarchist, but I don’t disagree with him about a lot of stuff.
ESQ: Justin, there’s something I’ve been dying to ask you: Do you truly sleep on airplanes with no shirt on?
JT: This is a wild rumor.
ESQ: Let’s set the record straight.
JT: I said this on the SmartLess podcast, that I had recently gotten a call from my publicist where she said, “A tabloid is asking about you. They’re saying you’re a nudist on airplanes.” It was hilarious. And I was toying with the idea of issuing a statement, something funny like “Look, my body, my choice.” So I’m relaying this story to host Jason Bateman—I said, “Yeah, so I got this thing this week and they’re maybe going to run a story that I go naked on airplanes”—and he goes, “Yeah, but you do go naked on airplanes.” I’m like, “What?!”
WH: [Laughs]
JT: Jason and I had flown from Los Angeles to London on one of those twelve-hour-long flights overnight and he reminded me that after they had shut down all the lights and everything was quiet in the airplane—and we’re in little pods, we’re not in 38J—I had taken some clothes off. I think I took my shirt off and maybe my pants. But I was definitely wearing something under that. And I tucked in and went to sleep.
ESQ: Sure.
JT: Jason came over to me at one point and said, “Hey man, what are you doing?!” He was in the full pajamas—like, the slippers and a toothbrush sticking out of his mouth. I’m like, “I’m going to sleep! No one is going to see!” And I had a blanket! So anyway, it was actually correct that I was essentially naked on an airplane, but not really naked.
WH, laughing: But are you missing the part of the story where you went and visited Jason and you were nude?
JT, *really* laughing: I’m missing the part of the story where I poured myself a gin and tonic and took it to the back of the plane and started chatting up other customers. I mean, look, if it’s a long-haul sleeping flight…I’m not going to fall asleep in my jean jacket!
ESQ: Okay, but there is a big range of clothing options between sleeping in a jean jacket and sleeping shirtless.
WH: If I had Justin’s body, never would I put on clothes. I’d wake up in the morning and I’d say, “Well, okay, I’m ready to go.”
JT: You don’t put a tarp on a Ferrari on the street!
ESQ: Neither of you is a stranger to viral moments. How do you both approach reading the comments or engaging with fans and haters online?
JT: The Internet is like this really big high school, and why on earth would you walk around it checking every room and broom closet for the bully to kick your ass? I don’t linger.
ESQ: Justin, you’ve certainly experienced being inside the maelstrom of social-media users theorizing about your personal life, mainly in your divorce from Jennifer Aniston. What’s it like to be on the other side of that?
JT: There’s something to, once you’re out of that, where I want all of my relationships to exist within the four walls of whatever room we’re in. And I’m not trying to be evasive, but I talk to Jen—I don’t talk about Jen. People will always want to gossip and say things, but you have to find that balance. And having been in a public relationship, it’s much more fun not being in a public relationship. Me saying anything, even if it was something loving, it would just turn into a thing. So it’s a classic no-comment situation for me.
ESQ: Woody, what’s your relationship to the Internet?
WH: I don’t read it. It’s like when reviews come out for movies. I don’t look. Well, I did one time. I was in this play in San Francisco with Sean Penn in 2000. At one point, I was stretching in the place that I was renting there and there was an LA Times, and it had a picture of me and Sean on stage. I’d only been hearing, “Oh my God, the critics just love you! You’re going to be so psyched!” Well, it just so happened that the paper was open to the review, and I started reading it. Oh, it just went after me. It fucked me up for at least two, three performances. It’s a poison pill.
ESQ: But does anything ever get back to you, Woody? Like after your SNL monologue this winter that stirred up a lot of controversy. Does that register with you at all?
WH: Well, people told me it was, shall we say, trending. No, I don’t look at that shit. I feel like, “I said it on SNL.” I don’t need to go further with it…other than to say—well, no, I won’t. Never mind. That’s enough.…But it don’t change my life one bit. Not one bit, if the mainstream media wants to have a go at you, right? My life is still wonderful.
JT: I’ve had some real goes at Woody, and I can tell you, he doesn’t give a shit.
ESQ: Woody, you opened the Woods, your dispensary in L.A., last year. Any sense of disbelief, as an advocate for decades for the legalization of marijuana, that selling weed is now actually legal in this country?
WH: It’s surreal. I never thought that marijuana would be legal in any part of the country. War is lucrative, and the war on noncorporate drugs is no exception. So for that to have finally happened is mind-blowing, although the government takes deep cuts. In fact, the California government is destroying the legal side of this. It’s much more lucrative to sell weed illicitly. And customers would rather go illicit because it’s cheaper. It’s all because the government is so fucking greedy—but that shouldn’t take away from the fact that I’m very excited that it’s happening. It’s the most beautiful dispensary ever. I’m in L.A. right now, and I spent hours there yesterday. It’s great to be able to go out and smoke right there in the Ganja Giggle Garden. Justin doesn’t puff. He keeps his mind sharp. He’s very clear.
ESQ: Woody brings up a good point. What are your vices, Justin?
JT: A cocktail at night, occasionally. Weed is one of those things that can go south real fast for me. Like, if I have half of a five-milligram edible, I’ll have some giggles. If I have the other half, it could turn to tears and fears.
WH: Justin starts reaching for it and I’m like, “No, Justin. No!”
JT: It can quickly turn into an ambulance arriving and taking my pulse. [Mimicking a paramedic:] “You’re going to be fine.” Meanwhile, I’ve seen Woody high, but I don’t think I’ve ever seen him where he can’t still get higher.
WH, laughing: That’s my vantage point, too!
JT: It’s incredible.
Story: Madison Vain
Photos: Mark Seliger
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Editor-in-Chief: Michael Sebastian
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