10 Things You Might Not Have Known About ‘The Talented Mr. Ripley’

Anthony Minghella’s Oscar-nominated take on Patricia Highsmith’s crime novel remains wonderfully suspenseful a quarter-century on—and inspired another, non-Oscar nominated film you might be familiar with.

The Talented Mr. Ripley, which hit theaters on December 25, 1999, boasted one of the most talented casts of the late ‘90s. Matt Damon and Gwyneth Paltrow had already won Academy Awards; Cate Blanchett and Philip Seymour Hoffman would go on to win them; and the movie launched Jude Law to worldwide fame. 

Adapted from a classic novel by Patricia Highsmith and directed by Anthony Minghella, the film centers on con artist Tom Ripley’s (Damon) increasingly unhinged attempts to ingratiate himself in the life of spoiled rich kid Dickie Greenleaf (Law). It racked up nearly $130 million at the global box office, picked up five Academy Award nods, and had people flocking to the Italian coastline to live out their ‘50s period drama fantasies. The film has also entered the pop cultural discourse a quarter-century after its release: First, as the obvious inspiration for the zeitgeist-defining, boundary-pushing dramedy Saltburn, and then its comparisons to Ripley, Netflix’s monochromatic take on the same source material. To celebrate its 25th anniversary, here are 10 things you may not know about the enduring classic. 

1. Jude Law nearly turned down the role of Dickie Greenleaf.
2. Matt Damon wasn’t the first choice to play Tom Ripley.
3. Cate Blanchett inspired Minghella to expand her character.
4. Law broke a rib while filming.
5. Damon lost 30 pounds to play Ripley.
6. Its most memorable scene was a last-minute addition.
7. Its first cut didn’t go down well with test audiences.
8. It’s filled with anachronisms.
9. It has a Deadpool connection.
10. The Talented Mr. Ripley influenced The Room.

Jude Law nearly turned down the role of Dickie Greenleaf.

Pre-Ripley, Jude Law was already a rising star: He’d appeared in Hollywood sci-fi films Gattaca (1997) and Existenz (1999) and was part of the tabloid-baiting Primrose Hill gang that also included Ewan McGregor, Jonny Lee Miller, and Law’s then-wife Sadie Frost. But it was his charismatic performance as perma-tanned playboy Dickie Greenleaf in The Talented Mr. Ripley that launched Law into the stratosphere. Remarkably, though, the Brit very nearly turned down the role that would also land him a coveted Oscar nomination. 

Speaking to Vanity Fair two decades after Ripley’s release, Law admitted that as an arrogant twentysomething, he believed that playing another pretty boy would be detrimental to his career, saying, “I was thinking at the time that what I should really be doing is just playing character roles and hunchback, just trying to find real weird, twisted characters.” Luckily, the actor realized that working with a director who’d previously helmed a nine-time Academy Award winner (1996’s The English Patient) would probably be a good idea. 

Matt Damon wasn’t the first choice to play Tom Ripley.

Alain Delon, Dennis Hopper, John Malkovich, and, most recently, Andrew Scott have all portrayed The Talented Mr. Ripley’s titular character on screen over the years. But for many, no one embodied his conniving but charming spirit more effectively than Matt Damon—but the “definitive” Ripley very nearly missed out on playing the antihero at all. 

Minghella’s first choice of actor to step into Ripley’s brown brogues was Leonardo DiCaprio, who had just starred in Titanic. But when the playboy passed on the opportunity, the director was forced to look elsewhere. Tom Cruise, Edward Norton, and at one point even Jim Carrey were just a few of the names thrown into the mix before Damon entered the fray. “After I saw Good Will Hunting, I was convinced he had the goods,” Minghella later acknowledged. “And being a writer himself would better understand the issues at stake.”

Cate Blanchett inspired Minghella to expand her character.

Cate Blanchett received a Best Supporting Actress BAFTA nomination for her scene-stealing turn as wealthy socialite Meredith Logue in The Talented Mr. Ripley. But the character, who didn’t appear in Highsmith’s novel, was initially intended to be just a minor one. It was only when Minghella recognized her star power during their first meeting that he quickly gave her more dialog to play with.

“Every time I picked up the screenplay the part of Meredith got a little bigger,” Minghella wrote in a piece for The Guardian in 1999, noting how her performance drew from both classical training and Lucille Ball’s brand of screwball comedy. “She's a natural comedienne, a whole body actor whose love of dance is betrayed in the physicality she brings to each character,” he said. “But it is her voice, rich and thrillingly able to transform the accent and register, which marks her out as the real thing.”

Law broke a rib while filming.

Both Law and Damon suffered for their art while filming The Talented Mr. Ripley scene that left audiences open-mouthed in disbelief. In a twist that no-one saw coming (well, unless you’d read Highsmith’s book), Tom and Dickie head out for a small boat trip in the Ligurian Sea, only for the former to fatally pummel the latter with an oar. Both actors committed fully to the deadly tussle, and things got a little too physical for real. 

“There's always a sort of an extra 10 percent, 15 percent that comes out of you when you call, ‘Action,’ which, it gives you a margin of error and the unknown,” Law explained during a chat with Vanity Fair. “And we were throwing each other around in this, and there was no padding, it was a kind of wooden boat.” Although the Brit thankfully managed to protect his chiseled features—a prosthetic facial mask was used that spurted blood—he did end up with a broken rib.

Damon lost 30 pounds to play Ripley.

In preparation for playing an emaciated, opiate-addicted military man in 1996 war movie Courage Under Fire, Damon embarked on a remarkably intense diet that left him more than 50 pounds lighter. It also left him in need of medication to fix his damaged adrenal glands. But health woes didn’t stop him from offering a similar commitment to play one of cinema’s most dastardly conmen: Damon willingly lost 30 pounds to star in The Talented Mr. Ripley, embracing a regime which included running six miles every single day. If that wasn’t enough, the Oscar winner also had to spend a significant amount of time in the make-up trailer getting his body further beach-ready. Unfortunately, that didn’t mean copious amounts of fake tan, but instead a powder to make Ripley look far paler and pastier than Paltrow and Law’s sun-seekers. 

Its most memorable scene was a last-minute addition.

The jazz club scene in which Dickie and Tom perform a playful rendition of “Tu Vuò Fà L’Americano” and the latter a heartfelt take on “My Funny Valentine” is one of The Talented Mr. Ripley’s most memorable. But it didn’t appear in the script until six weeks before shooting began: Minghella only felt compelled to include a little singalong after hearing the aforementioned Neapolitan jazz classic at a Capri musical event. Recognizing that it perfectly bridged the gap between mid-20th century Italy and the United States, he twice wrote “My Funny Valentine” into the film (a version by Rosario Fiorello also appears earlier on), allowing Damon to show off his vocal abilities. “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 said in an interview. “But he was extraordinary. His version of the song has beauty, pathos. You can't believe he's not a professional singer.”

Its first cut didn’t go down well with test audiences.

“A total disaster.” That’s how The Talented Mr. Ripley’s producer William Horberg described the first cut screened in front of a test audience. So how did opinion change so dramatically when the film was unleashed on the general public? All it took was a little foreshadowing.

The initial response was so negative because viewers hadn’t been given any indication as to which direction the story was heading—so when Ripley hits Dickie over the head with an oar, the result was both shock and distrust. In order to make the murder a little more palatable, Minghella took Sydney Pollack’s advice (“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”) and significantly darkened the introduction to its sun-dappled 1950s world. He opted for a Hitchcockian title sequence (soundtracked by an eerie Sinead O’Connor-sung aria), opened the film with its dramatic closing shot, and had Ripley ominously narrating, “If I could just go back, If I could just go back, if I could rub everything out—starting with myself, starting with borrowing a jacket...”

It’s filled with anachronisms.

The Talented Mr. Ripley’s production team no doubt went through each shot with a fine tooth comb to ensure that its setting convincingly replicated coastal Italy circa 1958. Unfortunately, numerous anachronisms still managed to slip through. 

Jazz purists would probably be aghast at the sight of Miles Davis’s Tutu during Tom’s post-San Remo get-together with Marge: the album was released 28 years later. There’s also the blue American passports, which in the 1950s would have been green; the use of miniature Christmas tree lights that didn’t enter the market until the ’70s; and the fact that the Venice skyline is occupied by the type of construction cranes that would have been far too advanced for the time. Even the film’s sole scene in New York struggled with period detail: Clearly visible in the background is the Sony Tower, which was built in 1984.

It has a Deadpool connection.

Eagle-eyed Deadpool 2 viewers may have spotted that the yokel ranting about toilet paper, played by Damon, was credited as Dickie Greenleaf, the name of the man who Tom kills and subsequently takes the identity of in The Talented Mr. Ripley. And this isn’t the only time that the 1999 classic has been referenced in popular culture.

In “The Talented Mr. Stewie,” a 2001 episode of Family Guy, Stewie keeps noting the comparisons between a boat-based murder plot and what he assumes to be a Hitchcock classic. That is, until Chris puts him straight that the scene in question is from The Talented Mr. Ripley (while also incorrectly describing it as a remake of a French movie). And in “Nine Lives Cat,” the seventh season episode of horror comedy anthology Inside No. 9, Steve Pemberton’s author Ezra mentions liking Law’s performance and how he’d make the perfect detective if his latest novel was to be adapted for the screen.

The Talented Mr. Ripley influenced The Room.

In addition to contributing to the golden cinematic age of 1999, The Talented Mr. Ripley is also partly responsible for inspiring the best worst film of all time. The awards favorite left such an impression on a then-unknown Tommy Wiseau that he felt compelled to become a filmmaker himself; the result was a similar, if slightly less acclaimed, tale of a love triangle gone wrong: the so-bad-it's-good masterpiece The Room. 

“The movie had bludgeoned him to within an inch of his emotional life," Wiseau’s friend and co-star Greg Sestero wrote in his memoir The Disaster Artist about their watch of Ripley. Sestro also noted that there were several parallels between Ripley and his eccentric pal, including their secretive pasts, deceptive behavior, and natural intensity when it came to establishing friendships. (Thankfully, Sestero clarified, “I didn’t think Tommy was a killer like Tom Ripley.”)

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