Natasha Lyonne: ‘I was my high school’s pot dealer, and then I got a Woody Allen movie’

It’s an overcast morning in Los Angeles, and Natasha Lyonne is thinking about heterosexuality. “Having a baby with a guy, getting the picket fence, putting an American flag on the f***in’ front lawn – that’s definitely not my fantasy of winning at life. If that’s what we’re calling ‘straight’, like… f***in’ keep it.” Lyonne has played gay so often and so well, most significantly in the cult conversation camp comedy But I’m a Cheerleader and in the Netflix smash Orange Is the New Black, that today she’s more or less the LGBT community’s favourite straight person. But, Lyonne says, it’s not quite as simple as that.

“I don’t know that I fully identify with the quote-unquote ‘straight’ experience,” she says. Her distinctive rasp is in evidence – imagine the love child of Joe Pesci and a New York City steam grate – but it’s softer since she quit cigarettes earlier this year. “Though I also don’t want to claim anyone else’s experience that I’m not actually living. Like if a hot guy walks through the room… baby, I’m lookin’. So I guess that makes me straight?” Still, her identity is a little more nuanced. “I look at sex more as… ‘hmm, what’s this mischief I can get into?’ I’m in this third category. My sexuality and gender is more like… merry prankster.”

Lyonne speaks in a kind of free-associative whirr, sharing the strangest, funniest stories you’ve ever heard. The 44-year-old actor, writer and director inhabits a few different roles in conversation: film scholar, stand-up comic, wise mentor. “I’m assuming I’m your elder,” she (correctly) guesses at one point. “I’m also gonna go ahead and assume that I’m at least your mother on a technical basis? Or your grandmother? Based on the DNA research we did ahead of the Zoom?” Neither is very likely for our 14-year-age gap. Still, she tells me I shouldn’t be afraid of leaving the house, but also that I should value my solitude. “I think of us both as men of letters,” she says, before recommending I read more books. I’ve been speaking to her for all of five minutes.

For much of her early fame, Lyonne was Hollywood’s foremost misfit. Teen blockbusters from the turn of the millennium decided she was sidekick material – she sat on the sidelines in American Pie (1999), for instance, sharing sexual wisdom to its cast of skittish virgins. In Scary Movie 2 (2001), she’d been possessed by Satan and shot in the face before the opening titles. She always seemed somewhat out of place and out of time, like Elaine Stritch if she fell down a wormhole in the Sixties and emerged three decades later to share scenes with Tara Reid. When Woody Allen aged out of playing himself in his movies, she was one of many actors – among them Kenneth Branagh, Sean Penn and Robin Williams – roped in to serve as surrogates for his kvetching neuroses. Only she pulled it off, despite being all of 16 when she filmed his Everyone Says I Love You (1996).

Her indies from around the same period matched her off-kilter rhythm: as a popular girl fighting off her gay instincts in the aforementioned But I’m a Cheerleader (1999), or as a rueful yet witty teenager in the brilliantly askew coming-of-age movie Slums of Beverly Hills (1998). Lyonne never hit the A-list back then, though, so when she nearly succumbed to heroin addiction in the mid-Noughties – following a tumultuous few years of arrests and being subjected to voyeuristic treatment by the New York tabloids – only her ride-or-die fans paid much attention. Likewise, when she got clean by the end of the decade, and had to fight for employment, empathy and respect.

But then, in 2013, something unexpected happened: Lyonne became more famous and successful than ever before. Orange Is the New Black cast her as a sardonic, imprisoned heroin user, a role that blurred the lines between fact and fiction and earned her an Emmy nomination. In 2019, she created and starred in Russian Doll, Netflix’s surrealist exercise in Jewish ennui and big-city melancholy. She played Nadia, who dies over and over again when her doomed 36th birthday keeps repeating itself. Its second season, released last year, ploughed even deeper into Lyonne’s psyche, exploring inherited trauma, mental illness and the Holocaust. Less probing yet just as brilliant is her new series, Poker Face – showing on Sky Max and Now – in which she plays human lie detector Charlie, who stumbles, episode by episode, onto strange mysteries across the US. Rian Johnson, of Star Wars: The Last Jedi and Knives Out fame, created it for her personally. It was renewed for a second season before its first had finished airing.

“I can no longer claim outsider status,” Lyonne laughs. “I claimed it for so long, but reality is reality, you know? That’s over now. I know how special all of this is, but having been on the other side of it, I also know how tenuous it is, too. In the 40 years of this career, I’ve had maybe 10 different ‘15 minutes of fame’. They come and go, so who knows how long this run lasts?”

Lyonne is video-calling from her living room. I only see her briefly before she switches off her camera (“Nobody needs to see this,” she cracks), but she looks like a rock star, rubbing at her eyes beneath a nest of red hair. She moved to LA last year, partly to try it out after decades of thinking of it as “a company town”, and partly because of its standard of living. “I got old and got a swimming pool,” she explains. “Because that is the evolution of life.”

Lyonne did not choose to act. Her mother and father, Jewish eccentrics who bounced between vocations until their deaths in 2013 and 2014, respectively, were caught up in a “narcissistic fantasy of fame”, she tells me. At five, she was asleep on Meryl Streep’s lap in an adaptation of Nora Ephron’s Heartburn. At six, she was a regular on Pee-wee’s Playhouse, a manic children’s entertainment series fronted by Pee-wee Herman, the guileless alter ego of comedian Paul Reubens. Lyonne’s upbringing was difficult, an all-consuming cycle of auditions, troublemaking and family upheaval, which included a two-year stint in Israel at the behest of her dad, who was being pursued by tax collectors. At the turn of the Nineties, she returned to New York with her mother, where drama continued. “I was my high school’s pot dealer, and then I got this Woody Allen movie and they were like… that’s too many things, so they expelled me.”

An on-set tutor on Everyone Says I Love You opened Lyonne’s eyes to filmmaking, introducing her to works by Federico Fellini, John Cassavetes and Robert Altman. Inspired, she enrolled in a film course at New York University, but found herself wildly overqualified among students who had barely seen Apocalypse Now, let alone 8 ½. When the dean of admissions insisted that she also take a class in astrology alongside film, she dropped out (“I was like, I don’t play with astrology, honey”).

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Instead, she educated herself. Stumble into a Manhattan repertory screening of a Bogart film in the mid-Nineties and you’d have probably found Lyonne – “It’d be six little old ladies and me, just in awe.” Her film education, though, proved pretty useless when she began getting regular acting work. After Slums of Beverly Hills, she turned down Dawson’s Creek and only said yes to American Pie after rejecting it several times – so desperate to get her on board, Universal Pictures ended up paying her more than everyone else in the cast. But I’m a Cheerleader was a creative reprieve, yet she remembers the press tour for the film being particularly draining. When I spoke last year to her co-star, Clea DuVall, she recalled being terrified during interviews for the film because she wasn’t yet publicly out. Lyonne, meanwhile, was constantly asked whether she felt “courageous” for playing a lesbian.

“It was the most offensive thing in the world,” she says. “Like when they’d say to Heath Ledger and Jake Gyllenhaal, too, how ‘courageous’ it is. F*** you! How dare you say that? Or like, ‘Why are you on the cover of Out Magazine with Clea DuVall but you’re not identifying as gay?’ Like, f*** you! It’s the cover of Out Magazine and Clea and I f***in’ love each other to death. So we’re gonna do our sexy little photoshoot. Nipples out, baby, let’s go! That’s why!”

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She and DuVall remain best friends to this day. They anointed one another “orphans”, as they’d both grown estranged from their parents by the time they met, and Lyonne says that, years later, she and their fellow Cheerleader co-star and BFF Melanie Lynskey – today of the time-hopping cannibal series Yellowjackets – “pretty much” walked DuVall down the aisle when she got married. “We were like, ‘All right, you’re our baby.’ We basically decided early on that we were going to take care of each other in this life.”

It’s no real surprise that the three of them – along with eternal cool girl Chloe Sevigny – bonded around this time. All were individualistic, artistic young women who’d found themselves on the fringes of a glossy teen movie era.

“The world hadn’t caught up to girls like us,” she says. “Like why was everyone making us feel as if there was something wrong with us? It’s funny, though, like me and Clea were, I guess, famous teen actors, but we were never allowed to feel ‘normal’ or ‘in the club’. It was made clear to us that we were broken in some way.” She says she gets so excited when she sees younger actors today. “You see Kristen Stewart or Elliot Page or Bella Ramsey, these people just owning their personalities and not apologising. There was so much apologising for existing in the Nineties. Part of the job of being a young actress was that you had to fall in line.” She says that her success back then also left her confused – she’d be cast in films because she was unusual, but then that same quality would be described as a problem. “They love that you’re different and that’s why you’re getting work, but they’re also gonna make you feel uncomfortable about it all the time. And let you know that you’re not this generic thing in a spaghetti-strap number.”

It was also around this time that Lyonne’s life took a turn. She’d always dabbled in drugs, but by 2001 her use had spiralled. She still has the chest scar from the open-heart surgery she underwent following an overdose. “I was very seduced by that Kerouac fantasy of dropping out of life, just getting on the Greyhound and discovering what the world was about,” she says. “This being a euphemism for my junkie years, obviously.” When she watched movies like Midnight Cowboy, about scuzzy hustlers in a Manhattan comprised of little but sex work and addiction, or baroque art films by Nicolas Roeg, she had “swelling feelings” that convinced her she needed to jump into the worlds they depicted. “I wanted to walk out of the theatre after seeing Once Upon a Time in America and go to the f***ing exact cobblestones to understand it, you know? By some f***ing grace, it all worked out, but there were a lot of hairy years in there.”

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She sighs, audibly retching at the memory. “I really did the thing, you know what I mean? And I did a lot of that s*** after already being, like, a sort-of famous teenager on the cover of magazines. So it was definitely confusing. And if you told me back then that that was going to be the journey, I probably would have said, ‘Keep it – I’m not strong enough for it, just gimme something easier.’ Yet now, at 44 years old, I am deeply moved that I got to have a specific journey. Because just on an empathetic level, like… I’ve been to prison and I’ve been to the Chateau Marmont, you know what I mean? I’ve been in the f***ing award ceremonies, and I’ve hung out on the streets. And there are beautiful characters and little f***ing monsters everywhere.”

She still can’t quite believe she’s ended up here: that Parks and Recreation star Amy Poehler made an NBC comedy pilot for her in 2014; that when it didn’t become a series, Poehler co-created Russian Doll with her; that Netflix let her take such big, personal swings with the show; that Rian Johnson casually said he’d love to write something for her, and then presented her with Poker Face. People believe in her.

Poker Face is a series that fizzes with classic, mystery-of-the-week charm, Charlie inexplicably winding up at the centre of countless murders. “She’s naturally an optimist,” Lyonne says. “She has the sun on her back and Big Lebowski energy, you know? And when she sees something that feels off, she has this need to solve the puzzle. Or if she sees an underdog being mistreated, she just can’t stand for the injustice of it.”

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It’s something she relates to personally. “I just want the kids to be OK,” she says. “I very much like to hold all of the outsiders together and let them know that they’re in a gang – like we can have our own gang.” When conversation turns to the political climate right now, particularly for queer people, Lyonne becomes indignant. “How dare anyone think they have the right to tell people how to live their life? Or tell somebody if they can use the f***ing bathroom or not? Or decide that girls don’t get to have abortions? Believe me, everyone is having a hard enough time being a human being all by themselves – straight, gay, f***ing white and Black alike. Like we’re all on this ride together trying to figure out why we’re supposed to work so hard knowing that we die in the end. We’re all in the same existential problem. So the idea that you’re gonna make it more difficult by causing unnecessary suffering? I hate it. I really just can’t stand for it.”

It’s why she thinks queer people have always been drawn to her. That and, well, “I’m a broad,” she jokes. “But that’s been a gift and a curse. I have this fantasy of being a wallflower, and someone asking me on a date, and I’m the shy girl ashamed to take up space.” I can’t really picture it. “The gift of it, though, is that I feel very held by the gay community, and understood. And there’s a lineage to it.” She conjures images of the Lizas and the Barbras of the world. “And I’m so proud to be a part of it.”

For a moment, she seems to time travel. “And we’re all gonna end up together, me doing my f***ing Vegas act, you know what I mean? I’m there, wearing my kaftans,” she says, laughing. “And we’re all gonna go party.”

‘Poker Face’ is on Sky Max and Now