10 Lesser-Known Facts About ‘The Talented Mr. Ripley’

Anthony Minghella’s Oscar-nominated adaptation of Patricia Highsmith’s crime novel continues to deliver gripping suspense even 25 years later—and it also inspired another popular film, albeit without Oscar recognition.

Released on December 25, 1999, The Talented Mr. Ripley featured one of the most acclaimed casts of the late ‘90s. Matt Damon and Gwyneth Paltrow were already Oscar winners, while Cate Blanchett and Philip Seymour Hoffman would later earn their own Academy Awards. The film also catapulted Jude Law to international stardom.

Based on Patricia Highsmith’s iconic novel and directed by Anthony Minghella, the movie follows Tom Ripley (Damon), a con artist whose desperate efforts to infiltrate the luxurious life of Dickie Greenleaf (Law) spiral into chaos. The film grossed nearly $130 million worldwide, earned five Oscar nominations, and inspired countless fans to visit the Italian coast to relive its ‘50s-era charm. Decades later, the film remains culturally relevant, first as the clear inspiration for the bold dramedy Saltburn and later through comparisons to Netflix’s black-and-white adaptation, Ripley. In honor of its 25th anniversary, here are 10 intriguing facts about this timeless classic.

Jude Law almost declined the role of Dickie Greenleaf.

Before Ripley, Jude Law was gaining recognition in Hollywood, having starred in sci-fi films like Gattaca (1997) and Existenz (1999). He was also part of the high-profile Primrose Hill group, which included Ewan McGregor, Jonny Lee Miller, and his then-wife Sadie Frost. However, it was his portrayal of the charming and sun-kissed Dickie Greenleaf in The Talented Mr. Ripley that catapulted him to global fame. Surprisingly, Law initially hesitated to accept the role, which later earned him an Oscar nomination.

In an interview with Vanity Fair 20 years after Ripley’s release, Law confessed that as a young actor, he feared playing another attractive character might harm his career. He stated, “I thought I should focus on quirky, unconventional roles instead.” Fortunately, he reconsidered, recognizing the value of collaborating with a director who had previously won nine Oscars for The English Patient (1996).

Matt Damon wasn’t the original pick for Tom Ripley.

Over the years, actors like Alain Delon, Dennis Hopper, John Malkovich, and Andrew Scott have all taken on the role of Tom Ripley. However, Matt Damon’s portrayal is often considered the most iconic. Despite this, Damon almost didn’t get the chance to play the cunning yet captivating antihero.

Minghella initially wanted Leonardo DiCaprio, fresh off his success in Titanic, to play Ripley. However, when DiCaprio declined, the director had to consider other options. Names like Tom Cruise, Edward Norton, and even Jim Carrey were floated before Matt Damon was ultimately chosen. Minghella later admitted that Damon’s performance in Good Will Hunting convinced him of his talent, and his background as a writer made him uniquely suited to understand the role’s complexities.

Cate Blanchett’s presence inspired Minghella to develop her character further.

Cate Blanchett at the Los Angeles premiere of ‘The Talented Mr. Ripley.’ | Steve Granitz/GettyImages

Cate Blanchett earned a Best Supporting Actress BAFTA nomination for her standout performance as Meredith Logue, a wealthy socialite in

The Talented Mr. Ripley. Originally a minor character not found in Highsmith’s novel, Meredith’s role was expanded after Minghella recognized Blanchett’s talent during their first meeting, giving her more lines and depth.

“Each time I revisited the script, Meredith’s role grew larger,” Minghella wrote in a 1999 article for The Guardian, praising Blanchett’s blend of classical acting and Lucille Ball’s comedic flair. “She’s a born comedienne, a physical performer whose dance background shines through in her movements. But it’s her voice—versatile, rich, and capable of shifting accents and tones—that truly sets her apart as an exceptional talent,” he added.

Law sustained a broken rib during filming.

Both Law and Damon endured physical challenges while shooting the shocking boat scene in The Talented Mr. Ripley. In a dramatic turn of events (unless you’ve read Highsmith’s novel), Tom and Dickie’s peaceful boat ride turns deadly when Tom attacks Dickie with an oar. The actors’ intense commitment to the fight scene led to real injuries.

“When the camera rolls, there’s always an extra 10 to 15 percent of energy that comes out, creating room for spontaneity and unpredictability,” Law told Vanity Fair. “We were wrestling in a wooden boat without any padding.” While a prosthetic mask protected his face, Law wasn’t so lucky with his ribs, which he fractured during the scene.

Damon shed 30 pounds to embody the role of Ripley.

Matt Damon, Jude Law, Gwyneth Paltrow, and Jack Davenport at the UK premiere of the film in February 2000. | Dave Hogan/GettyImages

To portray a gaunt, drug-addicted soldier in the 1996 war film Courage Under Fire, Damon underwent an extreme diet, shedding over 50 pounds, which later required medical treatment for his adrenal glands. Despite these health issues, he committed to a similar transformation for The Talented Mr. Ripley, losing 30 pounds through a rigorous routine that included daily six-mile runs. Additionally, Damon spent hours in makeup to achieve Ripley’s pale, sickly appearance, contrasting sharply with the tanned looks of Paltrow and Law.

One of the film’s most iconic scenes was added at the last minute.

The jazz club scene, featuring Dickie and Tom’s lively performance of “Tu Vuò Fà L’Americano” and Tom’s emotional rendition of “My Funny Valentine,” stands out as a highlight of The Talented Mr. Ripley. Interestingly, this scene wasn’t in the original script and was added just six weeks before filming. Minghella was inspired to include it after hearing the Neapolitan jazz classic at a Capri event, realizing it perfectly connected 1950s Italy and America. Damon’s singing impressed the crew, with music supervisor Graham Walker noting, “His version of the song has beauty and depth, making it hard to believe he’s not a professional singer.”

The initial test screening of the film didn’t resonate well with audiences.

“A complete disaster.” That’s how producer William Horberg described the first cut shown to test audiences. However, the film’s reception improved dramatically upon its public release, thanks to some strategic foreshadowing.

The negative reaction stemmed from the audience’s lack of clarity about the story’s direction. When Ripley suddenly attacks Dickie with an oar, it left viewers shocked and confused. To make the murder more digestible, Minghella followed Sydney Pollack’s advice: “If the bus is headed to hell, passengers should know when they board.” He added a darker tone to the opening, including a Hitchcock-inspired title sequence with Sinead O’Connor’s haunting aria, began the film with its climactic final shot, and included Ripley’s ominous narration: “If I could just go back, erase everything—starting with myself, starting with borrowing a jacket...”

The film contains several historical inaccuracies.

Despite meticulous efforts to recreate 1958 coastal Italy, The Talented Mr. Ripley features several anachronisms that slipped through during production.

Jazz enthusiasts might be shocked to see Miles Davis’s Tutu playing during Tom’s gathering with Marge post-San Remo, as the album wasn’t released until 28 years later. Other inaccuracies include the blue American passports, which should have been green in the 1950s, miniature Christmas lights that weren’t available until the 1970s, and modern construction cranes in the Venice skyline. Even the New York scene falters, with the Sony Tower, built in 1984, clearly visible in the background.

The film shares a surprising link with Deadpool.

Sharp-eyed fans of Deadpool 2 might have noticed Damon’s cameo as a character ranting about toilet paper, credited as Dickie Greenleaf—the same name as the man Tom murders and impersonates in The Talented Mr. Ripley. This isn’t the only nod to the 1999 film in popular culture.

In a 2001 episode of Family Guy titled “The Talented Mr. Stewie,” Stewie repeatedly compares a boat murder plot to what he thinks is a Hitchcock film. Chris corrects him, explaining it’s from The Talented Mr. Ripley (though mistakenly calling it a remake of a French film). Similarly, in the seventh season of Inside No. 9, Steve Pemberton’s character Ezra praises Law’s performance, suggesting he’d be ideal for a detective role if his novel were adapted.

The Talented Mr. Ripley had an impact on The Room.

Alongside its contribution to the iconic films of 1999, The Talented Mr. Ripley also played a role in inspiring what many consider the best worst movie ever made. The critically acclaimed film left a lasting impact on Tommy Wiseau, then an aspiring filmmaker, motivating him to create his own flawed yet unforgettable love triangle story: the cult classic The Room.

“The movie emotionally devastated him,” Greg Sestero, Wiseau’s friend and co-star, wrote in his memoir The Disaster Artist, reflecting on their viewing of Ripley. Sestero also observed striking similarities between Ripley and Wiseau, such as their mysterious backgrounds, manipulative tendencies, and intense approaches to forming relationships. (Though Sestero reassured, “I never thought Tommy was capable of murder like Tom Ripley.”)