The first test screening for The Talented Mr. Ripley was, as producer William Horberg remembers it, “a total disaster.” The early cut of Anthony Minghella’s 1999 film, adapted from Patricia Highsmith’s 1955 novel, plopped its eponymous con artist (Matt Damon) into a seaside Italian town—where aimless scion Dickie Greenleaf (Jude Law) had started living with his girlfriend, Marge (Gwyneth Paltrow)—as if he’d fallen straight from the sunny Sicilian skies. Where did Tom Ripley come from, why was he there—and wait, less than an hour in, why did he kill Dickie on a rowboat way out in the Ligurian Sea? The crowd rebelled. “When the oar came down on Jude Law’s head, it was really as if the oar had come down on the audience’s head,” Horberg says. “They were totally unprepared for the movie to take that violent left turn.”

Sydney Pollack, whose company Mirage Enterprises financed Ripley, gave the director a piece of advice as they discussed the inevitable edit to follow: “You can drive the bus wherever you want to go, but if it says ‘hell’ on the front of it, you’ve got to let people know when they’re getting on board.” So Minghella, fresh off an Oscar win for 1996’s World War II drama The English Patient, rejiggered Ripley’s first few minutes, invoking the ghost of Hitchcock a few times along the way. The jagged new credits sequence echoed North by Northwest. The music called Vertigo to mind. Minghella also established a flashback structure, beginning the film on its final shot, and wrote a haunting aria with composer Gabriel Yared that hummed to the action of the new opener—and he convinced Sinéad O’Connor to perform it. He even peppered in the slightest bit of foreshadowing, with Tom reflecting via narration, “If I could just go back, if I could rub everything out—starting with myself, starting with borrowing a jacket….” The rest of the movie went unchanged. Upon hitting theaters on its Christmas Day release, it debuted as a box office winner.

The Talented Mr. Ripley was always a study in contradictions. The film assembled what was arguably the most beautiful, auspicious ensemble of any Hollywood movie that decade. Shortly after being cast, Damon went on his Oscar-winning Good Will Hunting run and played Private Ryan in Steven Spielberg’s lauded war epic. Paltrow won her Shakespeare in Love Oscar months before Ripley’s release; one of her fellow first-time nominees was Elizabeth’s Cate Blanchett, a pivotal supporting player in Ripley. Law was the only core cast member still seeking a breakout, and he found it in Dickie Greenleaf, his smoldering, cocky portrayal serving as a direct launch to hunky stardom as well as an Oscar nomination.

But then there was the matter of the actual content: a tricky, moody, sexy antihero saga that also happened to be frankly queer, stuffed with murder, and avoidant of any sort of feel-good ending. “Our actors had been catapulted into a level of stardom that they did not have when we shot the movie, so the audience was coming with a whole different lens of expectation,” Horberg says. “Matt Damon, Gwyneth Paltrow, the director of The English Patient—it all seemed to promise an epic love story.” Ripley delivered the furthest thing from that, of course—something that, 25 years later, appears far more impressive and relevant, even if back then it felt radically out of time.

Horberg, who won an Emmy in 2021 for producing The Queen’s Gambit, had wanted to adapt Ripley for years. Eventually he and Mirage commissioned Minghella to write the script for hire, while The English Patient was stuck in preproduction limbo in the mid-’90s. Minghella, who died in 2008, wasn’t yet a big enough name for the studio to consider him as a director. After he’d written the Ripley script, he began prep to film The English Patient, while soft offers to direct Ripley went out to legendary filmmakers like Roman Polanski, Mike Nichols, and Bernardo Bertolucci. “Some weren’t available, some weren’t interested,” says Horberg. Then The English Patient, distributed by Harvey Weinstein’s Miramax Films, premiered as a global sensation, won nine Oscars including best picture, and turned Minghella into the hottest director in town. Fortunately, the Ripley job was still open.

Initially an arty gamble developed at Paramount, the project had sudden momentum and embarked on a storied casting journey. The role of Tom had been offered to Leonardo DiCaprio, whose Titanic was about to make him a huge star; he said no. Jim Carrey really wanted to play the part, but Horberg says that the conversations with him “never went anywhere.” Things took shape once Weinstein came in to cofinance. “Harvey had basically decided that he was going to be involved in whatever Anthony did next, come hell or high water,” Horberg says. Weinstein brought in Damon and Paltrow, who had future Oscar-winning work in the pipeline for Miramax but weren’t yet A-list enough to decline a risky if rewarding script. Law wasn’t either, but he still turned Ripley down outright three times. “His agent’s like, ‘You die on page 45, Jude!’ ” Horberg says. “But [Minghella] got really, really convinced that he couldn’t make the movie without Jude, and his persistence paid off.”

Add Blanchett and a few other rising stars, and a dream team assembled. “It was high-profile from day one,” says strategist Tony Angellotti, who helped run the Oscar campaign. Coming off of her own dizzying awards run for Shakespeare, Paltrow expressed some reluctance to get back on the trail: “So far, I’ve only felt sort of the traumatic part of it,” she told the Los Angeles Daily News around Ripley’s release. “It goes on for months, and it’s so exhausting and draining. I mean, you think, ‘Is this some popularity contest?’ ” (When Paltrow told The New York Times in 2017 that Weinstein, now serving a 23-year prison sentence for rape in New York, had made unwanted sexual advances toward her in the mid-’90s, it became even clearer how difficult that process had been.) But the bulk of the publicity was generated by Damon and especially Law, the true discovery of the cast. For director Sean Durkin, whose starry new A24 release The Iron Claw hits theaters on December 22, Law’s work in Ripley was so memorable, it informed his decision to cast the actor two decades later in his marital drama, The Nest: “It’s one of the great performances and one of the great characters.”

Law is only one of many ingredients that make Ripley almost obsessively rewatchable. Minghella hooks the viewer with that foreboding prologue, then delivers a glittering slice of Euro escapism. We meet a very tan and shirtless Dickie and a rather aloof Marge by the beach of Mongibello, where Tom introduces himself as an old Princeton classmate who just happens to be on holiday. (Needless to say, he did not attend Princeton.) He worms his way into their lazy lives, boating with them to Rome and San Remo and back again, hinting at his shape-shifting nature along the way: his terrifyingly spot-on impersonation of Dickie’s father (James Rebhorn), his talent for forging signatures, his rapid research when pretending to match Dickie’s love for jazz. In Ripley’s final hour, Dickie’s boorish bud Freddie (Philip Seymour Hoffman—yes, another eventual Oscar winner) observes of Tom, “You’re a quick study, aren’t you?” He’s next on Tom’s kill list.

What exactly is Tom’s game as he apes, then essentially becomes, Dickie? In Highsmith’s novel, his sexuality is mostly coded or cruelly commented upon. But Tom’s obsession seems to extend beyond a desire for status. “We felt in several ways the book needed to be reconsidered for the time that we were making the movie,” Horberg says. This included making explicit Tom’s attraction to Dickie and his experience as a repressed gay man in the 1950s. Ripley’s hottest scene, a chess match between Tom and Dickie by the bathtub, finds the latter nude and soaking. Desire burns in Tom’s stare, and he risks giving himself away when asking if he can join him in the bath—retreating as Dickie rejects him, then staring again as Dickie dries off. Minghella’s script also introduces two core new characters in Peter (Jack Davenport), a comfortably out musician who falls for Tom post-transformation, and Meredith (Blanchett), an heiress who runs in Dickie’s social circles, both of whom further prod Tom’s deeper sense of self by flirting with him. Tom’s private relationships with the two come to a head in Ripley’s climax, leading to a chilling, quietly tragic denouement.

The moment we observe Tom truly fall in love with Dickie, meanwhile, wasn’t initially scripted at all. At an event in Capri a few months before production began, Minghella watched a live performance of the song “Tu Vuò Fà L’Americano” that felt like a meeting of mid-century America and Italy. He returned home and decided to use it to anchor a scene in which Dickie and Tom attend—and later, sing at—a jazz club together, along with the romantic “My Funny Valentine.” “That was not in the script until probably six weeks before we were shooting,” Horberg says. Joy and longing pulsate through their performance, which unlocks a more human dimension of Tom. The sequence may be the film’s most vibrant and memorable. “This many years later, anytime I mention the movie, we talk about the scene in the jazz club,” says Durkin. “It’s something that’s lived for so long.”

Ripley landed in a fascinating period of transition for LGBTQ+ representation. Backlash against the “gay serial killer” trope had mounted aggressively following ’90s smashes The Silence of the Lambs and Basic Instinct, while queer respectability was going mainstream—this was the prime era of Ellen, Will & Grace, and so on. Anxiety abounded as to whether Ripley would be accepted as middlebrow entertainment given the climate. “I’m desperate that no one infer a connection between his actions in the film and his sexuality,” Minghella told The New York Times in 1999. “But it’s a sorry state of affairs if you can only write about a homosexual character who behaves well—that’s another kind of tyranny.” Ultimately, gay audiences largely embraced the film because of its rich subtext and unapologetic sense of fun. “The movie struck me as both capital-G Gay in terms of the homoerotic content, but then also very small-g gay in terms of the travelogue aspect and the beautiful people in clothes,” says Shinan Govani, an author and columnist who covered the gay press’s reaction to Ripley back in 1999. “It fulfilled both gay hungers at the same time.”

So the publicity campaign leaned in. “They went head-on in terms of playing to gay audiences and speaking to the gay quotient of the movie,” Govani says. “They didn’t shirk from it.” Most significantly, Damon participated in an extensive cover story for LGBTQ+ magazine The Advocate. Along with a photo shoot, he gave a long-form interview where he discussed all things gay, including the false rumors flying around him and Ben Affleck at the time: “The question of whether Ben and I are gay is so awkward in a lot of ways—there is no right way to answer it without offending somebody.” As for Tom’s provocative characterization, Damon said, “If you go into the theater thinking he’s a ‘gay serial killer’ and not a tormented, sensitive human being—then you may as well stay home.”

This surely reflected Minghella’s own perspective on Ripley; he said in 1999, “There’s so much nihilism in film right now. If I’m going to tell a story that’s so bleak and so much a journey of a soul, if in the end Ripley was just going to go about his business, what’s the journey?” But going into its release, debates over the right way to sell such an unusual studio film led to less nuanced packaging. “They felt they should market to the widest possible audience, and so it was not Italy, it was not gay, it was not opera, it was not jazz, it was not 1950s—not all the things that we loved about the movie,” Horberg says. “They really leaned into the killer-thriller sale and Matt Damon’s charm: ‘Beneath the smile lurks the beating heart of a killer.’ It was super hard for Anthony to get his head around that. They were not the values of the movie he had made.”

Despite strong reviews overall, Ripley did not wind up as one of the year’s breakout hits. “It was considered brave. There was admiration for the effort,” says Angellotti, the awards strategist. “The only question was, Is there an audience for it?” This question proved multipronged. Because of Ripley’s $40 million budget, the domestic $80 million gross constituted a modest commercial success. The haul of five Oscar nominations—excluding best picture, where Ripley was ignored—indicated the industry, too, held more respect than love for it, especially since it went home empty-handed. That remained the prime takeaway for years. As part of a year considered a landmark for American cinema, from awards darlings American Beauty and Being John Malkovich to cult classics Fight Club and Magnolia, Ripley has been historically overlooked among the top of that class. It’s barely more than a footnote in Brian Raftery’s hit 2019 book, Best Movie Year Ever, which dives deep into dozens of 1999 future classics.

Ripley may remain easy to underestimate because, despite the grim subject matter, it’s a hell of a good time, but it deserves a more serious reappraisal. (One may be coming; Netflix will soon release a new Ripley series starring Andrew Scott.) The film has not merely lived on but thrived for its surface pleasures—the gorgeous movie stars in their prime, the gorgeous locations across Italy, the gorgeous filmmaking by Minghella and cinematographer John Seale—as well as its moral complexity. In its flashy depiction of a closeted gay loner who scams (and eventually, kills) his way into rarefied air, such a tricky balancing act has made it an enduring favorite among younger directors and cinephiles. Its beauty and brutality go down like a fine Aperol. “Even with some of my favorite films, I need to be in a particular mood—but I never need to be in the mood to watch this movie,” says Durkin. “The more you become a filmmaker and understand filmmaking, the better it gets.”