Sean Baker’s new film, Anora, could have starred Tom Hardy and Ryan Gosling. Early in the project’s development, a producer interested in Baker’s script had wanted to woo the actors. Inside a coffee shop in West Hollywood a few weeks ago, the director recalled the man’s enthusiasm. “‘Those are your Russians!’” Baker told me the producer said of the characters they would play: two heavies who are tasked with breaking up an impulsive marriage between their wealthy Russian charge and his new wife, a 23-year-old sex worker from Brooklyn. “I was like, ‘Oh, I was actually thinking of casting real Russians.’” He laughed. “I like those guys, but that’s not the way I make my movies.”

Here’s the way Baker makes his movies: with small budgets, nonactors, a keen eye toward realism, and a determined rejection of Hollywood, even as his profile in the industry has risen. Sure, he constantly feels the tension between staying with his approach and straying from it; he was “almost seduced,” he said, by the aforementioned producer when he dangled the prospect of a $20 million price tag for Anora. But for now, he’s established himself as something of an oxymoron instead: the mainstream indie filmmaker. His work, focused on people who don’t tend to be movie protagonists—undocumented immigrants, adult-film stars—has landed him critical acclaim and major-awards attention. He’s built a dedicated following among cinephiles with his unconventional production process; he even rejects the typical practice of conducting test screenings for audience input. “It’s supposed to be my vision, so why would I ask for a bunch of opinions that would taint my vision?” he said. “It makes no sense. Like, if I fuck up, that’s on me!”

Besides, the strategy has been working for him. All of his films, including the cult favorite Tangerine and the Oscar-nominated The Florida Project, feel fully realized despite their scrappiness. They’re raw, intimate portraits of Americans who are often misrepresented or overlooked in pop culture, particularly sex workers. Baker’s love of telling outsiders’ stories isn’t why he chooses to remain one himself, however. “It’s not about the subject matter, because there are those movies made by the Hollywood studio system,” he said. “I just feel it’s so scary, because there’s just so many films made by committee.”

[Read: Red Rocket is a terrifyingly honest look at a shameless man]

Never has his conviction paid off like it has with Anora, his most accomplished work—and, as it continues its theatrical rollout, biggest box-office success—yet. The film stars an electric Mikey Madison as the titular heroine, better known as “Ani,” whose brassy exterior belies an earnest yearning for an easier life. When she meets Ivan Zakharov, a.k.a. “Vanya” (played by Mark Eydelshteyn), a client who turns out to be the obscenely rich son of a Russian oligarch, she’s whisked away into a drug- and sex-fueled romance that leads to the pair getting married in Las Vegas. Their union, however, results in an unpleasant collision with reality when Vanya’s family’s henchmen come to annul it.

Anora is a screwball romantic comedy, a high-octane thriller, and a poignant character study; for Baker, it’s also a watershed moment in his filmmaking. After premiering the movie at the Cannes Film Festival in May, he won the Palme d’Or, its most prestigious award. He reenacted the scene: He pointed to where his producers had been around him, and where Madison had sat. He demonstrated his eyes widening as he realized—in part because the other top contenders scored other trophies, which meant they were out of the running for the top prize—that he could be announced as the winner. And when his name was indeed called, he said, “it was my dream come true.”

The win has also led to “a somewhat existential crisis,” he told me. “This is the first time, actually, that I’m seriously having that, like, What’s the proper follow-up?, which is very dangerous. I try to avoid that, but up to this point, I haven’t had to really think about that.”

Since the beginning of his decades-long career, Baker has found himself drawn to stories about chasing success and stability in atypical ways. “There is something fascinating about, for me, the pursuit of this American dream, but people who have to pursue it who aren’t given the normal route, who can’t follow the normal route, because they’re not allowed to,” he said. His protagonists often glimpse an ideal version of their life just out of reach: In Tangerine, two trans sex workers spend Christmas Eve fighting off rumors that threaten their friendship and their clientele. In The Florida Project, the children living inside a motel create their own magic kingdom just miles away from Disney World, while their guardians do what they can to protect the kids’ youthful bliss. In Red Rocket, a washed-up porn star meets a teenager he believes could be his ticket back to semi-stardom; in the process of grooming her as his protégée, he takes advantage of the few relationships he has.

Baker feels a kinship with such characters, even if he points out that he, raised comfortably in suburban New Jersey, has never needed to rely on a criminalized and stigmatized livelihood himself. What resonates with him, he told me, is “that just-not-giving-up attitude, and the frustration, the feeling that sometimes it’s just never going to work out.” For much of his career, he pursued side gigs to make ends meet, spending years making money by editing wedding videos and actors’ demo reels; even today, the bulk of his income comes from outside his filmmaking. “I feel like there’s more than a little bit of hustler in me,” he said.

Mark Eydelshteyn as Vanya (left) and Mikey Madison as Ani in Anora. (Neon)

Still, the type of storytelling he’s interested in can easily read as exploitative rather than empathetic in the wrong hands. “You really do have to get the approval and the thumbs-up,” Baker said, “the signing-off of people who have had that experience … I don’t want a sex worker to see this film and just be like, ‘Who wrote this? This is not us.’” With Anora, as with his previous films, he was careful not to leer at the hardship. “That’s the first thing for me. I care about that audience more than any other.” So when he settles on a world to explore, he consults with members of the subcultures inhabiting it, and moves to the locations he plans to feature. He recruits nonactors, locals, and real-life sex workers to forge an authentic feel. On set, he encourages his cast to change any dialogue that sounds wrong, and to improvise so he’ll have plenty of tonal options to consider. He liberally edits what he’s shot; for the final cut of The Florida Project, for example, he ordered it differently from the script. He bathes his films in saturated colors, pushing back against Hollywood’s tendency to paint poverty in drab hues, and instead prioritizing the characters’ interiority—their humor, their pride, their wonder.

But if Baker previously assuaged his fears of inauthenticity by focusing on realism and meticulously incorporating his research, making a film as deliberately comedic as Anora required a different approach. Many of its set pieces are over-the-top to the point of absurdity—he referred to a late scene in which Ani, a hungover Vanya, and their exasperated minders disturb the peace inside a courtroom as “almost sitcom-level”—and he wanted his actors to push the humor as far as possible. A carefully choreographed home-invasion sequence, during which Ani fights tooth and nail to defend herself against the Zakharov family’s cronies, runs for nearly half an hour, filled with physical gags and F-bombs. Baker seemed thrilled by the ludicrousness, Samantha Quan, Baker’s wife and a producer on several of his films, told me: “You always know if a shot’s good, because you can hear him giggling.”

[Read: A meaningful chat with a flock of birds in The Florida Project]

Baker was bending his own rules, in other words: He ran the risk of the story feeling unreal, a tad too fantastical. And yet, he told me, even if the scenes became screamier and screamier, as long as he built toward its sober ending, he figured it would come together. The director sees Anora as an “overt comedy,” but it contains as much sadness as it does joy. Throughout the film, he trains his lens on Ani as the grounding force, even for the anxiety-stricken henchmen trying to break up her marriage, underlining the unusual, visceral bond they begin to build in the face of Vanya’s demanding family. Madison shows the light slowly fading from Ani’s eyes, worn down from constantly defending her self-worth and what she thought was a loving relationship. Baker’s other films produce such emotional sleights of hand too, but in less gradual ways, abruptly blurring reality and fantasy in their final moments: In The Florida Project, the children can reach the happiest place on Earth only in a dream. In Red Rocket, the protagonist sheds a tear as he lets his imagination run wild.

Perhaps that’s the key to why the director’s work feels specific yet universal, exuberant yet affecting. His films are balancing acts that reveal the so-called American dream to be a moving target—a seductive tease. Ani has bought into acquiring status and material wealth as an ideal; from the moment Vanya gives her a diamond ring, she starts fighting off fears that her Cinderella story might come to an end. When I observed that scrutinizing the American dream seems to be his films’ most consistent theme, Baker smiled. “Maybe,” he said. He considers his work inherently political, but if there are statements he’s trying to make, he told me, “they’re going to be disguised.”

Baker, too, has hovered just outside Hollywood’s spotlight. But because his films have started gaining more mainstream attention—especially with that Palme d’Or win—he knows he’s become a recognizable name among his peers. By remaining on the industry’s fringes, however, he’s built a precise filmography, right down to the same typeface he uses for every title—which is Aguafina, for the record. “I feel sometimes I’m stuck between two worlds, because I’m preaching about being independent and what that can mean, and having your vision untainted,” he told me. “But at the same time …” He shrugged. “I do love Hollywood.”

Anora won the top prize at the Cannes Film Festival and its star Mikey Madison has been widely praised.

As the young Donald Trump in the new film The Apprentice, Sebastian Stan slouches while he walks, pouts while he talks, and delivers every line of dialogue in a near monotone. Such behaviors tend to form the foundation for any recent Trump performance, but Stan delivers more than a comic impression. He finds complexity in these hallmarks: an instinctual defensiveness in those hunched shoulders, a frustrated petulance in the scowls. It’s precise work, in other words.

If only the film around him were just as carefully calibrated. The Apprentice attempts to chart Trump’s rise from real-estate businessman to future presidential candidate by focusing on his early career in the 1970s and ’80s, when, under the tutelage of the pugnacious lawyer Roy Cohn (played by Succession’s Jeremy Strong), he learned how to project power and not just crave it. The film is a muddy exercise in Trumpology that never answers the biggest question it raises: What does chronicling Trump’s beginnings illuminate about one of the most documented and least mysterious men in recent American history?

Not much, as it turns out. Yet the film struggled to find a U.S. distributor willing to back it during production; Trump is a polarizing figure, after all, and famously litigious. After its debut at this year’s Cannes Film Festival, The Apprentice indeed faced legal threats from the Trump campaign, leaving it languishing for months in search of any company that might help it reach American audiences—the ones most likely to see, and be affected by, the film. Briarcliff Entertainment, a small company that has begun to develop a reputation for picking up controversial projects, stepped in and launched a Kickstarter campaign to crowdfund the movie’s theatrical run, which begins Friday.

[Read: The most consequential TV show in history]

But the director, Ali Abbasi, an Iranian Danish filmmaker whose previous film, Holy Spider, turned a real-life serial-killer case into a fascinating drama, has insisted that The Apprentice isn’t meant to truly be about Trump; rather, it’s an outsider’s perspective on America through its most divisive avatar. “We wanted to do a punk-rock version of a historical movie,” Abbasi told Vanity Fair, citing Stanley Kubrick’s transporting epic Barry Lyndon as an inspiration. He, along with the screenwriter Gabriel Sherman, a journalist who has long covered Trump, intended to “strip politics” from the story altogether.

The idea of a politics-free film about Trump may be provocative to some viewers, but The Apprentice never quite achieves this goal. The action unfolds in two parts: In the first, the 20-something Trump, still attempting to carve out a real-estate career and climb the social ladder, is dazzled by Cohn’s celebrity. He tails him around New York City for much of the 1970s while absorbing Cohn’s three tenets for success: Attack, attack, attack; admit nothing, deny everything; and claim victory, never admit defeat. In the second part, Trump has come to embody those rules fully. It’s only a two-year time jump, from 1977 to 1979, yet it feels jarring, because the Trump of the ’80s is more ruthless than Cohn ever was. And that decision, to skip past depicting his shift toward callousness, prevents the film from fulfilling Abbasi and Sherman’s aim of interpreting America’s transformation. It drops plenty of tasteless hints at present-day Trump instead: A scene of him being intrigued by the potential new slogan for Ronald Reagan’s first presidential campaign—“Let’s make America great again!”—is played for laughs. When, during an interview, he scoffs at the prospect of launching a political campaign himself, the shot holds for an extra beat, as if daring viewers to chuckle along with him.

By omitting the years when Trump started coming into his own, The Apprentice delivers a summary of his character rather than an arc. Take his relationship with Ivana (Maria Bakalova), for instance: In the film’s first half, Trump is a hapless suitor, literally falling over during an attempt to impress her. In the second half, he is seen assaulting his now-wife in their home in a violent scene that likely drew the Trump campaign’s ire. (The scene is based on Ivana’s recounting of an incident in a 1990 divorce deposition, which she later recanted; Trump also denied the allegation.) The contrast underlines the difference between a power-hungry man and an actually powerful one, but it doesn't show us the trajectory itself. The Apprentice suggests that Cohn hastened whatever rot was already present in his protégé, but its early scenes portray the opposite—that Trump, at his core, was simply naive. He desperately attempts to contribute to his family’s real-estate business; he idolizes his older brother; he displays a simpering loyalty to Cohn. Abbasi may have wanted to avoid putting his finger on the political scale—to steer clear of sympathy or condemnation—but the result is a shallow, murky portrait.

[Read: HBO’s Roy Cohn documentary is a lesson for Trump]

Perhaps this lack of substance is meant to evoke the flimsiness of the TV show the movie is named after. But The Apprentice offers glimmers of more nuanced ideas. It is handsomely shot, the production design making 1970s New York look like it’s in a state of decay, with the grime extending to the staging: Trump, in one of the earlier, more dynamic scenes, corners Cohn in a bathroom to convince him of his worth. The best parts of the film engage with how Cohn boosted his own ego and drew considerable pleasure from molding Trump into his image; Stan and Strong deliver committed, electric performances in their scenes together. But the energy fizzles when The Apprentice descends into a supercut of the younger Trump’s lore. It re-creates some of his most braggadocious interviews. It shows his reported scalp-reduction surgery. It ends in 1987, with him meeting the ghostwriter of his memoir. When an ailing Cohn finally confronts Trump for avoiding him, the encounter feels perfunctory, a mere interruption of an extended clip show.

The Apprentice could have delved into the Trump persona or explored how it calcified. But by trying to avoid how Trump’s past reflects his current approach to politics—his zero-sum relationship to power, his pettiness and egotism—while simultaneously winking at viewers’ knowledge of him, the film lands itself in a trap. Abbasi and Sherman’s intent—to hold today’s Trump at arm’s length and dramatize his backstory in “punk-rock,” cheeky fashion—is inherently flawed, because separating Trump’s philosophies from his transformation as a public figure means dulling the story of any potency or relevance. Even the one relationship, between Trump and Cohn, that feels potentially insightful gets diminished by the end. The film becomes an exhausting reenactment of familiar events instead—a safe endeavor that coasts on its protagonist’s infamy.