Natasha Lyonne Photo: Larry Busacca/Getty

“Yo, yo, I’m excited. This is going to be funny,” Natasha Lyonne text messages me, urging me to join her on an apartment hunt she’d just started. “Host of characters. Yer missing out on the crazy lady.”

Lyonne’s East Village landlord just raised her rent, so the day before she’s due back on set to film season 2 of her smash Netflix women’s prison dramedy, Orange Is The New Black — which films at Queens’ Kaufman Astoria Studios and a defunct children’s psychiatric center in Rockland County — she’s trying to find new digs. So far, the brokers she’s met in a whirlwind of viewings before I arrive include a humorless man in “an overly warm blazer” at one apartment and a very nice woman with a beard and an emphysematous growl at another. “The one who looked like a dinosaur?” asks Max, the dapper 28-year-old French broker squiring her around to apartments. “She did look a little bit like a dinosaur,” Lyonne agrees.

On the street between apartments, we run into at least three people Lyonne knows, including her personal trainer (“You gotta get cut for prison,” Lyonne tells me later. “All that fingering – you need strong triceps”). “Is there something I’m missing?” asks Max, distressed. “Are you a celebrity? Are you famous? Everywhere I look, you say hi to someone.” The petite 34-year-old woman standing before Max with that distinctly unruly mane of dirty blonde hair and a T-shirt from the 1978 tour of the rock band Rainbow, is, indeed, pretty famous. Or infamous, depending on whom you ask. Lyonne’s plucky lesbian “junkie philosopher” character on Orange is informed in part by her own very public career implosion and struggle with addiction. And little do those brokers know that she’s charming them with a humor and delighted come-what-may attitude that can only truly be embodied by those who’ve clawed their ways back from the brink of death and have learned to take everything a little less seriously after that.

“Here’s my situation, all right,” says Lyonne, in an accent that’s a cross between a Jewish grandma and Marge Simpson’s hard-smoking twin sisters. “I’m living in a fucking beautiful building in a beautiful apartment the past five years. I have a 40-year-old man I live with and a small animal. The apartment got too small to really make it worth the raise in the rent.” The small animal is an adorable Maltipoo named Root Beer, and the 40-year-old man is her boyfriend of two years, Andrew, a former Times reporter she met at an Angela Davis rally in Washington Square Park during Occupy Wall Street. His pickup line, ironically enough, was about an L.A. sublet they were both looking at and both failed to get. “So instead we just started sleeping together, and now we have a new real estate situation,” says Lyonne. “I thought he was way too sophisticated and intelligent and reasonable to actually be my boyfriend. I thought it was going to be a one-night stand and I was just gonna suck out all his brains in one night,” she says, cackling. “He had a much better vocabulary when we first met.”

Max seems to be enjoying himself, but Lyonne isn’t an easy client. She doesn’t know if she wants to stay in Manhattan or move to Brooklyn; she doesn’t know if she wants to buy or rent; she kind of wishes a magical sublet would fall in her lap; and deep down, she doesn’t want to move at all. The only reason Lyonne, who grew up on the Upper East Side, is considering Brooklyn is because Andrew told her, she says, “that I’m not in touch, that I don’t understand that Brooklyn is, like, a thing.” She sighs. “Here’s hard evidence that I’m aging: When I was a little girl, the goal was to move out of Brooklyn, okay? My grandparents live in Flatbush, and I’m supposed to be trying to move back to Brooklyn? All of a sudden I’m just supposed to go with the flow and pretend that this is a reasonable move? Now so many people live there, you’re weird if you don’t live in Brooklyn. I don’t want to be a hipster. I want to be a fucking grown-up!”

“In the nineties,” she goes on, “nobody fucked with Brooklyn. Kokie’s was the only reason you went to Brooklyn,” she says, referring to the famed Williamsburg after-hours spot whose appeal is fairly obvious from the name. “That was the only time you went to Brooklyn, when you weren’t even present enough to understand you were on your way there.” We conclude a sweaty walk down to King St., which gets points for being a block away from her favorite place in the world, Film Forum, and find ourselves in a very odd duplex decorated only with a chandelier, a giant painting of a blindfolded ancient Roman, a framed photo of Justin Bieber, and a very elaborate and space-consuming setup for a driving video game. The buyer’s representative, a nice woman named Emily who’s cracking up at every one of Lyonne’s jokes, asks her what she does for a living. “I’m a professional real estate seeker,” says Lyonne. “I sort through rentals. I just have my rich boyfriend support me and I look for various homes for us to live in. It’s not easy, but it’s a life.”

Emily has a loft we could see later in Williamsburg, which coincides with another appointment near there that Lyonne has already made. Max will stay on the isle of Manhattan, and Lyonne lights up a Marlboro before heading into the subway for what seems like the first time in years. “Remember tokens?” she asks me, and then promises she’ll pay me back “the buck twenty-five, buck fifty” she owes for the swipe I give her.

“Are cigarettes cheaper in Brooklyn?” she wants to know. She once dated a man who lived off the Lorimer L Train stop, she muses. “And when we broke up, I left him with the entire borough.”

When we emerge on Bedford Avenue, Lyonne seems terrified. “You notice how everything just slowed down?” she asks. “Why is everybody moving so slowly?” We pass a blonde, dreadlocked hippie playing guitar. “A handsome young person you could probably sleep with is the Williamsburg equivalent of a homeless guy,” says Lyonne. “Look at this guy. You could totally take this guy home for a hot meal.” Seconds later, we pass a sofa on the curb. “He has sex with women on the sofa in broad daylight, while reading The Tin Drum and strumming his guitar,” says Lyonne. “Welcome to fucking Brooklyn. Does anyone over 50 live here?”

Every few blocks she stops to check in with another broker. “I feel like I’m sexting,” she says. “You get a little rush.” She had her first brush with real estate at 17, when she bought her first apartment in Gramercy, a penthouse with a wraparound terrace, after dropping out of NYU’s Tisch School and using two semesters of tuition to make the down payment. “It was fucking brilliant, and I’ve been trying to reclaim that thunder ever since.”

We’re taking a load off on a bench outside a coffee shop, while a couple of neighborhood Dominican guys blast some hip-hop-ified Steve Miller Band song and jump in and out of a well-tended classic car. Watching that seems to singlehandedly convince Lyonne that Williamsburg could possibly be all right. “I always feel a real kinship with scenes like this,” she says. “Reminds me of being a teenager on the Upper East Side, being like, ‘Yo, whatcha got in that car? Also do you have any apartments for rent?’” She cracks up. “You know, you get a twenty bag of weed and a couple apartments.”

The guys have turned up the volume and are now dancing. “They’re definitely high, are they not?” she asks. “I like that it’s been too long and now I don’t even know when people are on drugs.” Still, drugs are all anyone in the press seems to ask her about, even with the runaway success of Orange, or the many movies, like Kristen Wiig’s Girl Most Likely, that she’s started to appear in. On The View recently, she had to spend the entire segment relating her character’s heroin use to her own “I’m so old now, and also it’s so long ago. We’re working our way towards ten years,” she says. “It’s like, how much longer are they going to make me talk about this?”

Our Williamsburg adventure finds us meeting back up with Emily from the chandeliered apartment to see a gorgeous 1,200-square-foot loft that’s major sticking point is being a fourth-floor walkup. Lyonne contemplates installing a dumbwaiter or hiring a cabana boy before deciding that “I don’t want to write a check my ass can’t cash.”

Lyonne calls a livery cab, and soon we’re on our way to Schermerhorn St. (which Lyonne insists on calling “Shmmmermerhorn,” since she’s convinced that’s a made-up name). In the car, we talk about her renewed passion for acting. It’s always been her calling. Even before her professional debut on Pee Wee’s Playhouse at age 6, she was doing dramatic readings of stock tips from The Wall Street Journal for passengers on the Long Island Rail Road. “I would have done well as a gypsy child, I think. A circus baby. I coulda played a great street urchin or ragamuffin. Or just been one,” she says. “I certainly liked entertaining people and making jokes, but I don’t know necessarily if that’s what your child is prone to that you should necessarily put them in a real working industry at six years old. By the time I was 16, I was already an exhausted cynic.”

The wisest thing she ever did, she says, was really take the time off to get sober. “I mean, I didn’t have a 28-day drug problem. I had a take-five-years-off drug problem.” It helped that because of “my well-publicized drug problem, there was many years I couldn’t get work.” And she’s fine with that. “I mean, life is very short but life is also very long. I don’t know that there’s such a rush. I think I also needed a break just in terms of the child actor in me was tired. I mean, I’d been working from, like, 6 to 24, pretty much nonstop.” But after slowly re-proving herself in theater and TV guest spots, and “recommitting to my job and recommitting to life in general,” Orange came along, and it’s a game changer. She’d done quality movies no one’s seen, like Slums of Beverly Hills, as well as schlocky teen stuff everyone saw, like American Pie, but had never before experienced the confluence of doing something critically acclaimed that lots of people seem to be watching, too. Even Lou Reed is a fan and invited her to do his Sirius Radio show. (“It really was, like, the most meaningful showbiz moment I’ve had; Lou Reed is only my everything.”) Plus, she’s been having fun with the show’s racy content. One of her first scenes is eating out another girl in the open prison bathroom. “Yeah, that was meant to be a fisting scene,” says Lyonne. “But you can’t see that I’m fisting her on camera.”

“I knew that I recognized you,” our driver pipes up.

“I’m that fister!”

“I’ve been enjoying your show so far.”

“Thank you so much. I am that girl that ate out that girl on the show.”

After enough traffic to convince Lyonne that she probably never wants to move to Brooklyn, we find ourselves high above Boerum Hill. Looking on the Brooklyn skyline, she says she feels like she’s in New Jersey. “I think I’m just a little confused by the neighborhood, first of all,” she admits. “Because I don’t have any idea where I am.” The broker says he has a better apartment for us, a ground-floor two-bedroom pre-war on a quiet cul de sac in Brooklyn Heights for $3,700. Lyonne listens patiently, then asks, “And … how far is that from Manhattan?”

Outside the building, we run into Ethan Hawke and his 11-year-old son. Hawke and Lyonne did a play together, 2010’s Blood From A Stone, and now Hawke lives nearby. “If you live in this neighborhood, come over for a drink,” says Hawke, cheerfully. “Well, not a drink … ”

Lyonne steps out of the car at the cul de sac to see a gorgeous view overlooking Brooklyn Bridge Park, and then behind it, the financial district. “Is that Manhattan?” she asks, and is pleased to be affirmed. Then she turns around to see a man in a monk’s robe walking toward us. “I was hoping he’d be a samurai, have a sword, like Forest Whitaker in a Jarmusch movie,” she says. The cul de sac apartment is, she says, “not a winner, I’m gonna level with you,” and she fears that on-the-ground floor it might be “cock-a-roach-y,” but the next one on Henry Street is actually pretty close to what Lyonne has been looking for — an endless maze of rooms and space. The incredibly seventies kitchen, tiled in various shades of brown and white, is of particular interest. “I feel like swinging! This would be great for all my swingers’ parties,” says Lyonne.

“I gotta tell you, Brooklyn is growing on me. Sad to say, I’m getting the appeal,” she says, pausing for a cigarette before our final apartment. It’s a duplex around the corner from Brooklyn Bridge Park with 40-foot ceilings and wall-to-walled mirrored closets. Lyonne is pretty sold on the too-low interior balcony overlooking the living room. “You could totally get murdered here,” she says. But she can’t wrap her head around the owners living right downstairs. “What if we get in a fight?” she asks. “Every day, it’s hey Tina, hey Joey, hey Mom, hey Dad. I don’t know these people. They’re not my family. I don’t even speak with my real family. I’m confused about how you live freely, one night you want to come home and blare Jimi Hendrix, you want to have friends over.”

On our way back to the island, Lyonne appears to get calmer with every mile. “I have a real love affair with the city,” she says. “I just feel like when you’re up or when you’re down, the city really cushions you. I feel like I just have such the blood and bones of a New Yorker that I can almost imagine better, like, giving up the fight and not being able to afford the city and going out West, keeping a small place here, and then when I’m like 80, coming back here, living on the park and going to the theater. For the matinee.”

Safely back in the East Village, six hours after we started, she gives me a big hug and promises to help me in my own search for a new couch. “Listen, we had such a fucking epic day. I guess I would say that I’m not oblivious to the fact that this is hilarious and sort of a hectic way to do it, and not at all reasonable. I’m sort of doing it for my personal amusement, and the Andy Kaufman adventure of it all. I want to come to your place now. I feel very bonded. It’s fucking hard, New York real estate. What if I just moved in with you? That would be the best ending to this ever.”

Two days later, she emails and says she’s strongly leaning towards just re-signing her lease.

*This is an expanded version of an article that originally appeared in the May 13, 2013 issue of New York Magazine.