In August’s final episode of season one of I’m Dying Up Here, Showtime’s dramedy about a group of up-and-coming comics in ’70s Los Angeles, Cassie, played by Wellesley native Ari Graynor, is forced to contemplate her future. It’s not that things are going badly. It’s that they’re going great. Sometimes, Cassie learns, that’s just as unnerving.
“She’s had this whole journey, and success, and somebody says to her, like, ‘So what are you doing after this?’ ” Graynor says over iced coffees in the cafe at the deCordova museum in Lincoln. “And Cassie says, ‘What do you mean?’ Which to me felt like such a true experience of what it’s like in this business, where you think When this thing happens, it’ll be great. I’ll feel this way. I’ll finally be the person I want to be. And it’s just not the case.”
It’s tempting to declare 2017 a turning point for Graynor. I’m Dying Up Here, despite disappointing ratings, has just been renewed for season two, and she’s fresh from the Toronto International Film Festival, where her much-buzzed-about new film The Disaster Artist screened to rave reviews. (She’s in town to collect Tootsie, her Lab-beagle-Shih Tzu mix, who stayed with Graynor’s parents in Natick.)
But Graynor, who is 34 and has been acting professionally since elementary school, has been the subject of more than one magazine profile suggesting some project or other of hers is “the one” — the one that’ll push her over the edge, make her a bona fide star of the sort you might recognize on the street, or walking around a suburban museum. Real life, of course, doesn’t always follow the neatest narrative, and that’s perhaps especially true for an actor. After all, acting, as she puts it, is “the only form of creative expression you can’t do alone. You’re at the whim of other people. You largely can’t just pick and choose.”
And, for a while, other people’s whims tended to place her time and again as the brash, brassy comic relief, and with decent reason: It’s a character she’s pretty much nailed. She was still in high school at Buckingham Browne & Nichols in Cambridge when she landed a recurring role on The Sopranos as Meadow Soprano’s hot mess of a college roommate. In 2008’s Nick & Norah’s Infinite Playlist, she plays Norah’s boozy best friend, and she had a small part as a roller derby tough girl in 2009’s Whip It. A few other minor, if memorable, same-same parts followed before her starring turn in 2012’s For a Good Time Call . . . as a broke postgrad who starts a phone sex line with her best friend. That role let her shake the sidekick shtick, but it didn’t really help with the typecasting. Then came Bad Teacher, a 2014 CBS sitcom about a gold-digging platinum-blonde divorcee who becomes a private school teacher in order to snag a rich guy. Finally, it was her own show, she was the star. It was canceled after three episodes. Critics said she “deserved better.”
All of which is why, about two years ago, Graynor was feeling stuck. She wasn’t getting the roles she wanted, roles that felt like they had some purpose. Filled with self-doubt, she found for the first time in her life that auditioning had started to make her anxious. “There’s no job that I’ve ever done that I didn’t love at the time,” she says. “But it stopped feeling challenging; that fulfillment had started to be replaced with a little bit of emptiness.” After pursuing an acting career since the age of 7, she says, “I really was like, ‘It might not happen. Not everybody gets what they want.’ ” Part of the angst was related to being a thirtysomething. Her friends back home were getting married, buying houses, having babies, seemingly settling happily into the lives they’d chosen for themselves. Graynor didn’t feel settled at all, but she didn’t know what to do about it. “We structure our lives in such a way to eliminate as much unknown as possible,” she says. “I knew that the times when I feel most alive and vital in my own life is when I run towards the unknown. But when you’re out of the habit of doing that, it gets really hard and scary. What will we say? What will it be like?”
For nearly two years, she avoided acting. Instead, she started writing every day, finishing two scripts she hoped to produce, and published a few personal essays, including one for The New York Times about driving cross-country with her dad. She moved from LA to New York and got Tootsie, and they settled into a nice little place in the West Village (“I nest pretty hard,” she says). She started coming to Boston more often and began to crave nature, dreaming of a little land and a house in Western Mass. She tried to think of it less as a transition and more as a shift in perception. “Being an actor was always the singular dream,” she says. “For so long, I’d been so sort of one-track. But for a while, I wasn’t sure I was ever going to act again. And that was hard. But I liked discovering that there can be additional dreams on top of the main one.” The self-doubt wasn’t entirely gone, though. “Even after I started getting published,” she says, “I would at times ask myself, well, ‘Who am I to write? Who am I to direct?’ I’d have to tell myself, these are such silly questions. They’re questions men never ask themselves. They just do whatever it is.”
She was at her parents’ house in the late summer of 2015 when she got an e-mail from Jonathan Levine, who was directing the pilot for I’m Dying Up Here. He had her in mind for the role of Cassie, a woman trying to make her way in the male-dominated field of comedy — a rare character now, but even rarer in the 1970s. Cassie was perfectly imperfect, and Graynor loved her instantly. “She’s a woman that I actually know, which is one who is smart, has big dreams, is ambitious,” she says. “She is tough, she is vulnerable, she is loving, she is dependent . . . ”
And because life works this way sometimes, less than 24 hours later, “I got this text: ‘Hey, it’s James Franco,’ ” she says. “I thought someone was playing a joke. He said, ‘Do you know The Room?’ ”
The Room is, essentially, a story about a love triangle, and the brainchild of Tommy Wiseau, a struggling Polish-American actor who couldn’t get a break in LA, so he made one for himself. It’s been described as “one of the worst movies ever made” and “intoxicatingly awful,” derided for its low production values, poor dialogue, bad acting, and plotlines that range from repetitive to nonsensical. And people love it. It regularly plays at sold-out, often late-night, screenings for rowdy audiences who come dressed up like the characters, Rocky Horror Picture Show-style, and throw plastic utensils at the screen (nearly all of the artwork in the film features spoons).
Graynor was alone the first time she saw it, after Franco’s text. “I was clutching at imaginary arms next to me, just being like, ‘Oh my God, are you seeing this?’ ” she says. “You see these characters, you see what they’re shooting, and you sort of think This can’t be, this isn’t something that really happened.” At the same time, she could understand the appeal, and how, of all the bad movies in the world, this was one that people chose to cling to. “At some point, everyone involved [with The Room] was hoping they were making something great,” she says. “People respond to it because you can feel that soul in there. It’s a universal story of wanting to make your dreams come true.”
Franco told her he was producing, directing, and starring as Wiseau in a movie based on the making of The Room, and he wanted Graynor to join the cast, alongside his brother Dave, Seth Rogen, and Alison Brie (and, eventually, heavyweights like Bryan Cranston and Sharon Stone). In the movie, The Disaster Artist, out now, Graynor has a key dual role, playing both Lisa, Wiseau’s fiance, and Juliette Danielle, the actress he hired to play her in The Room. Graynor liked Juliette for the same reasons she liked Cassie: She could empathize. When The Room came out, Danielle suffered a lot of the fallout — it was a truly terrible movie and people weren’t exactly kind about her acting, or her nude scenes, which were less tasteful than she had been promised. “I think for Juliette, the experience of The Room was difficult, as it often is as a young woman where you want to be amenable, you want to be game, you’re a people pleaser,” says Graynor. “And Juliette and the Lisa character get the short end of the stick.” As Graynor puts it, expectations are often the biggest obstacles to overcome. She understands that feeling, too, even as she can’t help but be excited about The Disaster Artist’s potential — critics are already talking Oscar for Franco. “It’s so easy to fall into the good news, no matter how many times I go through it, and I always say I’m not going to buy into it,” she says. “But people really seem to be going nuts for this movie.”
Franco says he wanted Graynor for her talent. They were acquainted through mutual friends, and he’d seen her perform on Broadway. The role of Juliette is tough “because she is not a great actress, or at least is an actress saying terrible lines, but you can’t just cast a bad actress to play a bad actress,” he says. “Ari is an incredible actress, so she gave the character so much more resonance because her depth shines through the badness of the surface.” Franco points to one particularly awkward sex scene as an example. “It’s really the best scene in the film. Tommy is going nuts because he thinks he’s lost his best friend to a woman,” he says. “Ari played the actress who has to put up with an insane director, and by this point she is so over his bullshit, but she’s professional so she suffers through it. It’s actually a horrific situation, but Ari helps make it funny, which is incredibly important because we don’t want the audience to completely hate Tommy at this moment, even if he is acting like a maniac.”
When Graynor and I meet at the deCordova, on an unseasonably hot early fall weekday, it’s been less than 48 hours since The Disaster Artist premiered at the Toronto Film Festival. Fans started lining up at 10 a.m. for the midnight screening, followed by a Q&A with the headlining cast. “It was wild,” says Graynor. “The movie ended and I’d never seen anything like this. Literally not one person left the theater, and they gave it a standing ovation and stayed standing the entire Q&A. It was like being at a rock concert.”
But of course, the question looms: Now what? The deCordova is in its final days of a show about women painters of New England, and as we walk through the space — Graynor dressed vintage-chic in high-waisted flare denim, a peasant top, leather open-toed low-heeled sandals, and aviators — we lament not having taken some art history classes while we had the chance. “I like the colors in this one,” she says of a 2016 acrylic-on-PVC piece by Kristin Baker. “I just wish I had more context.” I’m not much of a help. She tells me about a project she’s been trying to get off the ground about German-born American sculptor Eva Hesse. Hesse died in 1970 at 34 and has since become known as one of the formative artists in 20th-century minimalist art among an all-male crew including Sol LeWitt, Carl Andre, and Robert Smithson. For Graynor, Hesse’s life story “opened up a real curiosity about art and about that time, and how different her work was from her male community of friends,” she says. “There’s something that resonates with me about that, especially since I so often find myself as sort of a lone female with a lot of men.”
In Hesse, Graynor found inspiration: An artist “so singular in what she was doing regardless of what the people around her were doing,” she says. “And that’s a very difficult thing to do.”
I’m Dying Up Here will begin filming season two later this month, and as she readies to rediscover Cassie, Graynor is looking to find a bit of herself in the character while also keeping her at a distance. Just because they’re similar, after all, doesn’t mean they’re the same, and Graynor doesn’t want to get stuck playing, well, herself. As Cassie wanted to fit in with the male comics, Graynor wanted to fit in with the male actors playing them. “I wanted to belong, I wanted to be part of things, I needed them as my community, and so I adopted some of their ‘one of the guys’ way of being,” she says. “But at some point, I realized, like oh, I’ve sort of been ignoring some of that softer, intuitive, loving part of myself. I would wonder: Am I feeling [a certain] way because this is what Cassie is feeling? Or because it’s what I’m feeling? How do you hold onto your own way of being?”
But, it seems, Graynor is finding her way — at least for the moment. She’ll play Washington Post correspondent Ann Devroy in 2018’s The Front Runner, a Gary Hart biopic by director Jason Reitman (Up in the Air). It’s a small part in a large ensemble cast, but a dream role of sorts — decidedly not ditzy, but also not Graynor.
Recently, she was home at her parents’ house, rummaging through a bunch of the “Ari boxes,” and found a book of stories she wrote when she was a kid. “There was this one called ‘Wishelina,’ ” she says, “and it was about this princess who wished for things that then would come true. And then, of course, her wish was to keep having things to wish for.” It’s the writer in her who recognizes the poetry of the moment. “When I read it,” she says, “it sort of broke my heart.”Alyssa Giacobbe is a regular contributor to the Globe Magazine.Send comments to firstname.lastname@example.org. Follow us on Twitter @BostonGlobeMag.