1. After pitching the film, Minghella had one stipulation: He wanted final say over who played his Tom Ripley, refusing to make the film unless he found the perfect actor to inhabit the role. "There are no bad people, " Minghella explained. "Inside your head it all makes sense. That was the key to finding an actor who could let you understand how he thinks and operates.
2. Leonardo DiCaprio reportedly turned down the role of the titular character before Damon, desperate for the role, was cast. "I threw my hat into the ring and begged for the job," Damon said.
3. So why was Damon, then just becoming a breakout star in Hollywood thanks to Good Will Hunting (which earned him and best friend Ben Affleck an Academy Award in the best writing category) and the Oscar-winning Saving Private Ryan, the director's pick to play the iconic literary villain?
"Someone cool would have distanced the audience," Minghella explained. "But Matt has a credibility, and warmth and generosity—such winning qualities—that make you want to go on that journey with him inch by inch. We've all at some stage known what it's like to feel excluded. We might even have pretended to be someone we're not in order to be accepted. But not many of us are flawed enough to kill for it. After I saw Good Will Hunting I convinced he had the goods. And being a writer himself would better understand the issues at stake"
4. As for the privileged Dickie Greenleaf, Minghella found his American in a relative unknown British star, with The Talented Mr. Ripley going on to earn Law an Oscar nomination. "I was looking for somebody who was charisma on legs, somebody you could imagine men and women being attracted to," Minghella said of casting Law. "Dickie Greenleaf is such a flame around which all these moths circulate...he's also capable of the kind of sternness Dickie had. It's not just about being a prince, it's also about having something quite metallic in him which I think he gets to very easily."
5. To play Dickie, the lean actor had to put on weight, with Law explaining, "I had to put on some weight because they play much more physical sports in school [in America]."
6. Damon, meanwhile dropped almost 30 pounds to play Ripley. "I have to run six miles a day, I can't eat this food, I have to learn how to play the piano, that's just a checklist, a shopping list of things you have to do every day," he explained.
7. Aside from dropping weight, Damon also had to be covered in make-up all over his body in order to make him pasty and much paler in comparison to the tanned Law and Paltrow.
8. Both leading men developed new musical abilities for their respective roles. Law learned how to play the saxophone, while Damon learned how to play piano and revealed his vocal talents during his performance of "My Funny Valentine" in the film. "When I first heard Matt was going to do the song himself, I assumed we were going to have to re-voice him, " music supervisor Graham Walker admitted. "But he was extraordinary. His version of the song has beauty, pathos. You can't believe he's not a professional singer."
9. The film's lush and glam setting in '50s-era Italy became an essential character, with the cast and crew filming on location in several cities to achieve the fictional (and idyllic) Italian seaside town of Mongibello, including Rome, Sicily and Naples. But it wasn't an easy shoot, with production often only having one day at each location to get their shot, which were sometimes hundreds of miles apart. We drew a map and from one street to another I think it was [a distance of] three hundred miles," Minghella once explained.
10. The coastal weather also didn't cooperate, seemingly wanting to rain on the crew's Italian parade at every opportunity. "One of the things that tormented us as filmmakers on the movie was we had to deliver this gorgeous Mediterranean world, this beautiful world of Southern Italy, and we could never get Italy to turn beautiful," said Minghella. "We would divide the scenes up, often into words, and go out and get two or three words and then it would start to rain and we'd have to go back in again"
Alas, all of the work paid off, as the film had audiences dreaming of a European holiday.
11. Of course, just as famous as the scenery were the clothes sported by the cast, particularly the main trio, with legendary costume designer Ann Roth earning an Oscar nomination for her work in the film. For Tom's look, most of the pieces were vintage items that were remade by tailors to be purposefully ill-fitting to highlight his standing, which Roth described as "very American east Coast but...from Sears." In the words of co-designer Gary Jones, Tom's signature corduroy jacket was "such a piece."
12. For Dickie, all of the clothing worn by Law was custom made by New York tailor John Tudor to show off his wealthy upbringing and current lavish (and lazy) lifestyle. "My job was to show this very well-off boy, Dickie, in Europe, on a very strict allowance, but with a sensational lifestyle," Roth explained. "I had him in a jacket and some shorts, or a jacket and some linen trousers, and that jacket had to reflect a very rich background. And if he had one or two made in Rome, it had to look that way."
13. As for Marge, whose still regarded as a film style icon to this day, Roth explained her chic wardrobe had more to do with an attitude than the actual pieces. "She doesn't buy her own clothes, they are her parents' purchases she had from school… but if somebody said where'd you get those loafers, she wouldn't have a clue," she explained. "That was not interesting to her. It's like the designer's names now, the Tommy whomevers." As the movie progresses, Marge's wardrobe goes from light linens and bikinis to darker tones and fabrics, reflecting the shift in her character as Ripley casts a shadow over her life.
14. The climactic boat showdown between Tom and Dickie, which ends with Dickie's death, proved as dramatic off-screen as on, with Law revealing to Yahoo, "We busted each other up badly on that: I did his rib in, he did my rib in, and I gave him a bruise around the neck."
15. You can thank The Talented Mr. Ripley for giving us the gift that is The Room, one of the best worst movies of all-time, as Tommy Wiseau was reportedly inspired to make his own film after seeing Minghella's masterpiece. "The movie had bludgeoned him to within an inch of his emotional life," Greg Sestero, Wiseau's friend and collaborator (and Mark in The Room) wrote in his memoir of the pair's first viewing of Ripley. (Oh, his character was named Mark after Wiseau misheard Matt Damon's first name.)
16. While he became the breakout star of the film, Law was admittedly nervous heading into production to share scenes with Damon and Paltrow, both Oscar winners. "I had to play this guy who was the focus of almost every scene and yet I was there with Matt and with Gwyneth, so I was a little nervous that here was this guy who had not done that many films having to use his bravado," he told BBC. "I rather relished that to be honest, it was quite a good way of getting rid of nerves, just sort of riding them."
17. Not a character in the source material, Minghella created Cate Blanchett's character Meredith Logue. Ironically, Minghella was looking for a Blanchett-type to play the supporting role and was surprised when the actress herself expressed interest in the small part. "I went home entranced and started writing more scenes for her character," the director wrote in a piece about Blanchett for The Guardian. "Every time I picked up the screenplay the part of Meredith got a little bigger."
Of taking on the smaller part, Blanchett, who would go on to earn her first Oscar nom for Elizabeth (losing to Ripley co-star Paltrow) said, "I've been surprised that people have not been talking about the role but about the size of the role, which I find such a bizarre concept."
18. While Damon's take on the character is arguably the most well-known, Ripley has been played by four other actors: Alain Delon (1960's Plein Soleil), Dennis Hopper (1977's The American Friend), John Malkovich (2002's Ripley's Game), and Barry Pepper (2005's Ripley Underground). Malkovich revealed to the BBC, I almost directed The Talented Mr. Ripley."
19. In Deadpool 2, an unrecognizable prosthetics-wearing Damon made a surprise (and brief) cameo as a character named Redneck No. 2. In the credits, the character is listed as Dickie Greenleaf.
20. In 2008, Minghella, one of the most noteworthy directors of his generation, passed away at the age of 54 after suffering a fatal hemorrhage following surgery for cancer of the tonsils and neck. Law, who would go on to work with Minghella on Cold Mountain and Breaking and Entering, was particularly devastated over the loss of Minghella, who became his mentor. (They were introduced via Law's mother, who directed one of Minghella's plays in the '90s.)
"It was a very special relationship, which I hoped would go on longer," he later told Variety. "Because of his passing away, it makes that feel all the more cherished."