After the success of The English Patient, director Anthony Minghella could do any movie he wanted. He decided to adapt a novel written by Patricia Highsmith, about a character named Tom Ripley. In 1999 (a great year for movies), the film headlined by Matt Damon was released. It wasn’t a success, but over the years, the movie has achieved cult status. Even Matt Damon says it’s his favorite movie he’s ever made.

The Talented Mr. Ripley is a movie about a talented scammer, before we used that word. And in a time when tech scammers are everywhere (just this year, we’ve had three different shows about them: The Dropout, WeCrashed, and Super Pumped: The Battle for Uber), it’s time to revisit this incredible movie. Let’s put on a ridiculous hat, get into a jazz club, sing tu vuo’ fa’ l’americano together, and talk about The Talented Mr. Ripley.

Matt Damon, The Villain

     Miramax International  

Tom Ripley lives without means in New York. The Greenleaf patriarch mistakes him for an Ivy classmate of his son, Dickie, who’s living it up in Italy. Tom accepts the Greenleaf money on a mission to bring the prodigal son back home. Once he meets Dickie, and falls under his spell, Tom changes his mind. What might start with infatuation and maybe love for Dickie ends tragically when he impulsively kills him. Tom decides to become Dickie and move to Rome, spending the rest of the movie living la dolce vita with Dickie’s money, while trying to evade capture. Ripley might be an American dreamer, who does what’s necessary to get a better life and change social class, but is it still the American dream if to become rich you have to kill several people?

For all these reasons, casting a good Ripley was the most important thing for Minghella, and Matt Damon was perfect for the role. Damon’s All-American boy scout look serves him well here, as he’s continually underestimated, in an incredibly layered performance. His Ripley is many people at once: scared, infatuated, charming, homicidal, uncomfortable in his skin, smart, and Machiavellian. Because of Damon’s acting, you believe every emotion felt by the character, in one of his best performances ever. He plays the character as tragic, giving him more humanity than in the books, but you can see Ripley’s ambition in everything he does. Damon didn’t play a real villain again until The Departed, and it’s a shame as it’s the kind of character he can excel at, as this movie proves.

Incredible Cast Starting Their Careers

The five most relevant actors in the cast of The Talented Mr. Ripley are Damon, Gwyneth Paltrow, Jude Law, Phillip Seymour Hoffman, and Cate Blanchett. All five have been nominated for Academy Awards, and all except Law have won. That’s an incredible cast for this movie that proves Minghella’s spectacular eye for actors. Damon and Paltrow committed to the movie before their biggest breaks: Good Will Hunting hadn’t been released yet, and she hadn’t signed on for Shakespeare in Love, although when Ripley was released, both had already hit it big. Paltrow might have been the most famous member of the cast, and gives a great performance as Marge. She gives the character dignity in what could’ve been a nothing part if it was someone else in the role. She’s empathic toward Tom and understands more than what seems at first sight.

Although he had already shot Gattaca, this movie made Jude Law’s career. As Dickie Greenleaf, he’s so charismatic, that when Marge says “When Dickie gives you his attention, it’s as though the sun is shining on you, and it’s glorious”, you believe it, as we can’t take our eyes off him. It’s the movie that put him on the map, and one of his best performances. Philip Seymour Hoffman had already appeared in some movies as a great character actor, but this might be the moment he became recognized as one of the best of his generation. In two years, he appeared in Magnolia, this movie, State and Main, and Almost Famous. His character of Freddie Miles is what changes the dynamic between Tom and Ripley in an all-in performance by Hoffman. He might only have five scenes, but you remember every one of them. He’s the biggest jerk ever; so sure of his position in the world as a rich, entitled American, looking over his shoulder at Tom every moment until his demise. And let’s not forget his memorable entrance, with a red Alfa Rome, in Rome’s piazza uttering his first sentence: “Oh God, don’t you want to f**k every woman you see, just once?”

Last but not least, is Cate Blanchett. Minghella liked working with her so much that he expanded her role for the film from what it was in the novel. Blanchett had already shot Elizabeth, but wasn’t known in Hollywood, and her performance as Meredith Logue shows the embarrassment of those who have it all. It might not be one of her greatest performances, but it showed she could create characters you wanted to root for who didn’t have that much on the page.

Great Patricia Highsmith Story

Patricia Highsmith had written the book Strangers on a Train, which became a movie success thanks to Alfred Hitchcock. But nobody talked about her, and she always felt she wasn’t appreciated enough in the States, so, she spent most of her adult life in Europe. The Tom Ripley saga might have been her other biggest success. She wrote five Ripley books, and there have been five movie adaptations (and a TV show is coming). Minghella’s film is still the best. Highsmith said of his creation, Tom Ripley: “I consider him a rather civilized person who kills when he absolutely has to.’ If there’s ’not much to be admired about him, she added, he was also ’not entirely to be censured’. Another of Highsmith’s obsessions was the different social classes and the inadequacy one could feel trying to spend time with someone richer, but also how can you change your luck. Her Ripley is a talented imitator and forger. Abilities that served him well in the ’50s world, where documents were easier to fake, and you could really create a new life for yourself. Leaving your past behind. Ripley explained clearly this idea when he says “I always thought it would be better to be a fake somebody, than a real nobody”

Minghella read the book and created an adaptation that suited his ideas and obsessions, moving the story to the late fifties and making Ripley a less-calculating sociopath (at least at first). The director described adapting the novel as “You’ve drunk the drink, and the taste that’s left in your mouth is what you go with,”. His film is stylized and shows an incredible and beautiful Italy in the ’50s. A country where sun, boat riding, parties, and fun are everywhere. He shot on the Amalfi coast (Positano), Rome, and Venice, and his Italy is the one where we would all love to live in.

Twenty-three years later, The Talented Mr. Ripley is still a relevant movie; one of la dolce vita, scamming, betrayal, death, and hurt. It has been impossible to recapture. Although, The Lost Daughter might be the closest someone has come. If you have a couple of hours, we recommend you give The Talented Mr. Ripley a re-watch. You won’t regret it.