When the boy arrived, the crew chanted his name: “Arleigh! Arleigh!” He smiled shyly and scooted onto the kitchen floor, to sit near Movie Mama. Heller crouched nearby, beaming. “We’re going to make a big, big mess,” she told him excitedly. Then she explained the game: Adams would tell him to paint on the butcher paper, but he shouldn’t listen; instead, he should get the paint everywhere. “Movie Mama’s gonna say, ‘Oh, no!,’ but it’s just a joke.”
Once filming began, it became clear that it wasn’t going to be simple to get the sweet, giggly Arleigh to make a big mess: the boy had been cast, in part, because he was so easygoing. From the sidelines, Heller shouted instructions—“Big mess! Big mess! Take the yellow bottle and squirt it!”—as Adams yelled for him to stop. Arleigh, a bit warily, squirted the bottle. It was easier when Adams urged him to paint on the paper: at one point, after he made a cute picture of a house, she asked him, “Do you live in this house with me?” Arleigh replied, adorably and sincerely, “No, I work here.”
The crew cracked up, but it was important to stay on schedule. Ultimately, Heller got the footage that she needed: Arleigh gingerly stuck his bare heels in the paint, then on the paper; he dabbed some on Adams’s nose; he hugged Adams, messing up her shirt.
Once Arleigh left the set, the crew filmed the final sequence, including the fall, which was done by a stuntwoman. Afterward, Adams knelt on the floor of the kitchen, swirling a dirty rag in circles, muttering miserably, “Happiness is a choice” and “What’s up with that duck?,” the nonsense lyric of a sing-along at Book Babies. Heller told Adams to imagine these strange words bubbling up inside her, as if she didn’t even realize that she was saying them out loud. Adams sobbed, “What’s up with that duck?,” then laughed, then sobbed again—and then, out of nowhere, she slammed her hand against the kitchen island, smearing it with green paint, making an even bigger mess. Everyone in the room jumped.
Heller was a classic theatre kid, an extrovert whose talents first blossomed in the warm terrarium of Alameda, California, the Oakland suburb where she grew up. In her family’s comfortably messy Queen Anne Victorian, every day was Art Day: her mother, Annie, a sweet art teacher with Mayflower roots, turned their yard into a fairy garden, making a footpath by laying ceramic tiles with insect designs; her father, Steven, a sardonic Jewish chiropractor from Brooklyn, was a woodworker. Heller’s brother, Nate, made music; her sister, Emily, became a comedy writer. But it was Heller, the oldest child, who was the family striver, a go-getter with an entrepreneurial streak. She formed a joke band called the Cactus Cows, handcrafting their merch; once, she rigged up her bedroom with a “Pee-wee’s Playhouse”-style system of pulleys. At eight, she got cast in the Alameda Children’s Musical Theatre, a professional troupe that staged children’s classics such as “Winnie-the-Pooh.” At nine, she got a role in a TV special about alcoholism. “I thought, This will completely turn her off,” her father told me, of watching his daughter repeat her lines again and again. “And she comes running over and goes, ‘Dad, I like it. I feel like I’m floating on air!’ She loved the attention, being in front of the camera.”
By the time Heller was in high school, Alameda, despite its charms, had begun to feel stifling to her. She was thrilled to be accepted by the tiny, rigorous theatre program at U.C.L.A., which taught Molière and the Meisner technique, rather than musicals. It was a high-pressure environment—you had to audition even to get into classes—but Heller thrived on the competition, winning Shakespearean leads and honing her craft. In her junior year, she fell in love with Taccone, another actor in the program.
During Heller and Taccone’s early years, their creative lives happily ran on parallel tracks. Both were the children of artsy, indulgent families with ties to the Bay Area: Taccone’s father was the artistic director of the Eureka Theatre, the celebrated venue that commissioned “Angels in America.” Together, they strategized about ways to break into an intimidating industry, with Heller booking jobs in regional theatres but mostly waiting tables at L.A.’s vegan mainstay Real Food Daily, slinging seitan to Alicia Silverstone and Moby. When Heller and Taccone bought a condo in Koreatown, they secured a dodgy loan despite the fact that the bulk of Taccone’s income that year came from unemployment and from two insurance payouts for car accidents.
Then, in a flash, Taccone’s career took off. In 2001, he formed the comedy troupe the Lonely Island with his junior-high-school buddies Andy Samberg and Akiva Schaffer, posting rap parodies and comedy shorts on the Internet years before YouTube existed. In 2005, Taccone was hired to write for “Saturday Night Live.” The couple jumped coasts, renting a place on the Upper West Side. It was a huge opportunity—and a shock to their relationship. Taccone, who had vomited twice before his first meeting with “S.N.L.” ’s Lorne Michaels, was working non-stop, terrified that he’d get fired. He was also suddenly a success in the comedy world, scoring viral hits with videos such as “Lazy Sunday” and “Dick in a Box,” and partying with celebrities including Natalie Portman.
Heller, meanwhile, was auditioning to play dead rape victims on TV police procedurals. After her triumphs at U.C.L.A., going on auditions felt like walking into a fog of misogyny—in TV and film, especially, Heller, with her half-Jewish background and wavy hair, was deemed “too ethnic,” insufficiently hot. One day, in the craft-services area on the “Nightbitch” set, we spoke about the grind of waitressing, and she riffed off another Maria Bamford routine by doing a quicksilver impression of the world’s worst customer demanding a bowl of boiling water with ice. “Boiling, boiling,” Heller cooed. “But I don’t want the ice to get all tiiiiny.”
“It’s such a nice day, I thought we could do this interrogation outside.”
Cartoon by Lars Kenseth
In 2006, not long before her and Taccone’s wedding, Heller flipped open a graphic novel that her sister, Emily, had given her for Christmas: Phoebe Gloeckner’s “Diary of a Teenage Girl.” The book, inspired by Gloeckner’s adolescence in the hedonistic wilderness of San Francisco in the nineteen-seventies, is narrated in the irresistible voice of Minnie, a fifteen-year-old who loses her virginity to her mother’s sad-sack boyfriend, Monroe. The story hit Heller like a fever: here, at last, was a nonjudgmental portrait of the artist as a teen girl, radical in its embrace of turbulent experience. Minnie was also exactly the kind of complex female role that Heller, who’d had her own wild years, was dying to play—and, in Hollywood, stories about teen-agers making messy mistakes, sexually and otherwise, were reserved mostly for boys.
For eight years, Heller fought to adapt “Diary,” initially staging it for the theatre, playing Minnie Off Off Broadway. After she aged out of the role, she wrote and directed an independent movie based on the material, casting Bel Powley as Minnie. With no background in the film industry, Heller worked new muscles, hustling for financing and pushing back on every no. When Gloeckner turned down Heller’s request for the rights to the book, she wrote long, pleading letters, then flew to the cartoonist’s home, in Michigan, and befriended her, eventually securing a yes. She persuaded Kristen Wiig, whom she knew through “Saturday Night Live,” to play Minnie’s mother in the movie. After failing to get her script into the hands of Alexander Skarsgård, whom she wanted to play Monroe, she reached him by texting the comedian Jack McBrayer, who’d described himself as a friend of Skarsgård’s in a magazine article that she’d read. She wrote and rewrote the material, ultimately completing ninety-nine drafts.
In 2012, Heller got a major break, scoring a slot in the Sundance Screenwriters Lab, with classmates who included Ryan Coogler and Chloé Zhao. Heller was then picked for the Directors Lab, which let her shoot a few scenes from her “Diary” script. She learned to incorporate (and ignore) notes; she found mentors, including Scott Frank, the screenwriter of “Get Shorty” and “Out of Sight,” who became a close friend. Ultimately, she raised a tiny budget—a million dollars—to film “Diary,” cutting expenses to the bone. Her sister-in-law designed the costumes. In 2015, Heller’s bet paid off, with “Diary” selling to Sony Pictures Classics in a triumphant late-night auction at Sundance. The movie won Best First Feature at the Independent Spirit Awards, launching her new career.
For nearly a decade, though, Heller’s vision for “Diary” had often felt as fragile as a dream—one that would surely dissolve, like the TV pilots that Heller had sold with a writing partner or the acting roles that she auditioned for. “Jorma was having this totally different experience of the world,” she said. “And he would, without meaning to, disparage things that I was doing. As not real. Or as not valid.” The couple long ago worked through these issues in therapy; Taccone has become Heller’s biggest supporter. But she hasn’t forgotten those years of feeling overlooked—talked down to by strangers at dinner parties, or pitied as a failed actress. Many women in her position would have accepted the one role on offer, that of “comedy widow”—the nickname that another “Saturday Night Live” writer’s wife used for herself—or had children, then used them as an excuse to give up. But Heller was too hungry. “That’s the truth of it!” she told me. “We both were ambitious. So there was a period where my career hadn’t caught up to my ambition, you know? And I was aching. There was something in me that wanted to come out.”
