Dream Role

Photo: Jenny Gage & Tom Betterton

Gwyneth Paltrow, her brother Jake, and I are discussing work-anxiety dreams. He claims he doesn’t have any. She says she has them all the time—especially a recurring dream, one that for anyone else wouldn’t be a work dream at all.

“It’s always the same,” she tells me. “I’m doing a Shakespeare play, and I don’t know the lines. It’s usually As You Like It. Or sometimes Hamlet, which I’ve never even been in. It’s the classic dream, not even an interesting variation!”

We’re sitting outside the Hampton Chutney Co. in Amagansett. It’s a glorious day: sunny, blue-skied, utopian. As I’d waited for the Paltrows to join me, I’d been vaguely aware of a grinning man wheeling around in circles on a bicycle in my peripheral vision. When they arrived, I abruptly realized who it was.

“Paul!” cried Gwyneth, and suddenly she was catching up with Paul McCartney.

This is the world one imagines the Paltrows grew up in: a kind of psychic Amagansett, with artists and stars suddenly spinning into view. The look-alike siblings—with their hooded eyes, beige coloring, and wide curling mouths, they are nearly twinlike—were raised in Los Angeles and Manhattan, the children of writer-director-producer Bruce Paltrow, who died in 2002, and actress Blythe Danner. Gwyneth, 35, became famous in her early twenties and iconic by the age of 26, when she won her Oscar for Shakespeare in Love; she’s married to Coldplay lead singer Chris Martin.

Meanwhile, her younger brother, 32, has stayed out of the spotlight, directing episodes of TV shows like NYPD Blue—though his own tastes are far more avant-garde, shaped by a high-school teacher who slipped him Godard at a vulnerable age (in contrast to Gwyneth, who cheerfully acknowledges she was a major John Hughes fan as a teenager).

Now Jake’s hitting the big, or at least the medium, time with his first film, The Good Night, starring his sister as a perfectly lousy girlfriend. (See David Edelstein’s review here.) The morbidly funny fable centers around Gary, a has-been rock star (played with perfect hangdog timing by Martin Freeman, the star of the British version of The Office) stuck in a loop of misery—a job writing jingles, a live-in relationship that’s shriveled to a bad habit, a best friend (and former lead singer) succeeding in every way he has failed. One night, Gary dreams of a woman so beautiful, loving, accepting, and funny that he just wants to stay asleep forever. It doesn’t hurt that she’s played by Penélope Cruz in a white tuxedo.

Despite a plot that might sound like romantic comedy, The Good Night is more stylized and oddball than that, with an undercurrent of what Jake calls “sweet nihilism”—an aesthetic closer to Godard than John Hughes. And as Dora, the protagonist’s waking-life girlfriend, Gwyneth is barely recognizable: pale, with a cape of dense brown hair, bundled in shapeless cardigans. “It was me physicalizing my New York Jewish half,” jokes Gwyneth. (Her rep as a shiksa goddess notwithstanding, the actress is in fact, as a friend likes to call her, “Gwyneth Paltrow, the descendant of ancient rabbis.”)

If Jake did have work-anxiety dreams, one can’t help but wonder if Gwyneth might star in them. She wasn’t Jake’s first choice for the role, for understandable reasons: He feared that casting his one-named icon of a sister might swamp his first real project before he’d even set sail. “I just read it as a sister and a friend,” she says. “But I thought it was really brilliant, and I said, would you ever want me to be in it?” Jake said no; she told him she understood. “But then he got this great cast together and I was like, come on, please?”

“I just felt more secure about it when we had these people,” explains Jake.

Though the character she plays is nobody’s dream girl, Gwyneth herself finds plenty to admire in the confident, impatient Dora, an art-world sophisticate who keeps reminding her boyfriend that his talents may be limited—she also praises the film’s candor about the danker corners of relationships, “the intolerance that happens when the communication has stopped, when people haven’t been diligent about being honest.” Yet she also recognizes that some viewers might find Dora a huge pain in the ass. In particular, she has noticed this reaction among “men, older men who’ve been married for a long time. They say, ‘I couldn’t stand her! You did such a great job of being the shrike.’ ”

“One couple broke up after a screening,” interrupts Jake.

“You didn’t tell me that!” says Gwyneth, looking amazed.

It’s not an effect that bothers Jake, who emphasizes repeatedly the movie’s “non-Hollywood” qualities. When Bergman’s Scenes From a Marriage aired on Swedish TV, he notes with amusement, it caused the divorce rate to spike. “That’s why we shot half the movie in 16-mm.,” he says—as an homage to Bergman.

Paltrow and Martin Freeman in The Good Night.Photo: Courtesy of Yari Film Group Releasing

For any artist watching it, The Good Night may feel itself like a bit of a work-anxiety dream, beneath its romantic trappings. At its heart is a very relatable anxiety: the fear that one’s best work has already happened—or may never happen. Anna, Gary’s tuxedo-clad fantasy, has the shining eyes capable of seeing genius where others see only mediocrity; she’s the perfect lover as perfect audience. It’s no wonder that in the hilarious, awkward sequence when Gary actually meets his dream girl (or at least, someone who resembles her), things go south: In the flesh, she has appetites and ambitions of her own, and is far less tolerant than her dream self.

Over time, Gwyneth says, she has learned to slip the skin of her own artistic self-doubt, to be proudest “when I’m pushing myself not to do my old tricks.” (It helps, she says, that the tabloid pressure has dropped, swerving “toward reality stars and wild-child-type things.”)

But Jake, who has just begun to dip a toe into this new realm of public judgment, insists that despite his famous family, he’s never really felt the anxieties his protagonist experiences—fears that are finally, he argues, delusions based on a false notion of success. “I almost wish the movie dealt more, in a literal way, with the fact that this is all self-perceived failure. If you have a success in your life, why can’t we hold on to that? Why can’t that be good enough for a lifetime, why do we always have to be ramping up?”

In any case, writing has become Jake’s favorite part of the filmmaking equation. “You’re alone, there are no questions about whether it will get made, whether it’s good or bad. It’s become a really enjoyable time. I’m in the apartment, I used those Bose headphones, my girlfriend [photographer Taryn Simon] was there with me half the time.”

What was he listening to? I ask. A variety of music, he says, ducking his head: “This guy Gonzalez, a lot of stuff.”

Any song in particular? “There were a few particular songs,” Jake finally confesses. “But I won’t say. I might want to use them in the next one.”

Dream Role