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‘The Talented Mr. Ripley’ at 25—Frank, Queer, and Ahead of Its Time – Monomaxos

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.”

Gwyneth Paltrow and Jude Law in The Talented Mr. Ripley

Phil Bray/Paramount/Miramax/Kobal/Shutterstock.

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.

Still from The Talented Mr. Ripley

Miramax/Courtesy of Everett Collection.

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.”

Cate Blanchett in The Talented Mr. Ripley.

Courtesy of Everett Collection.

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.
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