Released on Christmas Day 1999, The Talented Mr. Ripley was, in a very obvious sense, the ultimate Miramax movie. It paired writer/director Anthony Minghella (post-The English Patient, winner of the Academy Award for Best Picture) with headliners Matt Damon (post-Good Will Hunting, which earned him a Best Original Screenplay Oscar) and Gwyneth Paltrow (post-Shakespeare in Love, for which she won a Best Actress Oscar), as well as Cate Blanchett (fresh off a Best Actress nod for 1998’s Elizabeth). It was an adaptation of esteemed literary source material (Patricia Highsmith’s 1955 novel of the same name). And it boasted breakout turns from up-and-coming actors Jude Law and Philip Seymour Hoffman. A high-minded, star-studded affair destined for accolades and golden statuettes, it had prestige written all over it, and its sturdy box office ($128 million domestic) and five Academy Award nominations predictably solidified it as another hit for the unstoppable studio.

Nonetheless, 20 years after its theatrical debut, what’s most striking about The Talented Mr. Ripley is that, despite its illustrious pedigree, it’s a decidedly dark and demented sort of polished gem, all spectacular surfaces masking a fundamentally rotten core. To be sure, awards season always brings with it epics of a downcast nature. Yet even so, Minghella’s film remains a particularly nasty bit of big-budget business, enticing one with high fashion, opulent locales, and even prettier people—and then exposing everything on display as corrupt, broken, and empty. Romantic connection and class envy drive its narrative, and are eventually revealed to be warped desires that lead only to misery. But more fundamental still, it’s a story about the yearning to be something more—something different—and the lengths to which some will go to satisfy that craving.

And, in the end, the futility of such dreams.

The second big-screen version of Highsmith’s book (following 1960’s Purple Noon), The Talented Mr. Ripley concerns Tom Ripley (Damon), a pasty-faced amateur pianist who at a New York City cocktail party in the late 1950s is accidentally taken for a Princeton grad by wealthy shipbuilder Herbert Greenleaf (James Rebhorn). Desperate to see his playboy offspring return home, Greenleaf hires Tom to locate his wayward son Dickie (Law), who’s gallivanting around Italy. Tom finds the lothario in the (fictional) coastal town of Mongibello, where he’s shacked up with fiancé Marge (Paltrow) and screwing a young local beauty on the side. Having prepared for their first encounter by studying the jazz Dickie loves, Tom ingratiates himself into their company, using lies and deceptions to become their trusted friend and confidant.

Hailing from apparently humble origins, Tom covets Dickie in every respect. By the time they’re playing chess while Dickie luxuriates in a bath, Minghella’s camera tracing Dickie’s phallic cigarette as it moves from his waist/crotch to his lips, it’s clear that Tom longs to both be with, and be, Dickie—a conflation of sexual, social and identity impulses that The Talented Mr. Ripley addresses through slyly indirect means. Not that it isn’t easy to see why Tom is in awe of Dickie; from his first beachside moments, the magnetic Law comes off as a bronzed Adonis with an alluring smile and an arrogantly insouciant way about himself. He’s a selfish trust-fund hunk who lives the casual life, and is casual with the lives around him.

As suggested by a Saul Bass-ish opening that introduces us to Tom in slivers, the camera panning from his lit profile to his darkened side, The Talented Mr. Ripley is fated to take a sinister turn. Damon foreshadows Tom’s fractured, malignant inner life through conversational moments in which he lingers a moment too long before responding, suggesting the conniving calculations forming in his mind. Damon’s superb performance rests on his ability to embody Tom as both a cheery go-getter with a relatable aim—to improve his lot, and to become a part of this seductively ritzy world—and an amoral madman with no qualms about negating himself (and others) to attain what he wants. In a delightfully devious twist, the fact that he’s good at his impostor business only further endears us to him, no matter our understanding that his goal is insane—and, also, seemingly unachievable.

Even after Tom kills Dickie and steals his name—a crime born from Dickie finally recognizing Tom’s ambitious, ugly hollowness—the only person who instinctively identifies Tom as a dangerous charlatan is Dickie’s friend Freddie. Played by the great Hoffman with a limp wrist, a scarf around his neck, and self-important condescension dripping off his tongue, Freddie is the wrench in Tom’s master plan. More murder invariably follows, as do questions from the police and friends, as Tom’s desire to adopt Dickie’s life becomes a hopelessly complicated affair, replete with a relationship with textile heiress Meredith Logue (Blanchett) and mounting suspicions from Marge.

“ Played by the great Hoffman with a limp wrist, a scarf around his neck, and self-important condescension dripping off his tongue, Freddie is the wrench in Tom’s master plan. ”

Minghella shoots all of this with maximum glossiness, all shimmering oceans, stark silhouettes and mirror reflections. He visually alienates Tom in his posh frame while drawing us in through vistas of seaside Italian retreats and nightclubs where Dickie joyously riles up the crowd with his saxophone and, later, Tom wows Dickie with a swoony rendition of “My Funny Valentine.” The Talented Mr. Ripley trades in murder most exquisite, evoking its characters’ downward trajectories through their wardrobe choices and the increasingly constricting environs in which they find themselves. John Seale’s sumptuous cinematography drenches the action in sparkling light, filtered-by-the-sun haziness and murky shadows, accompanied by a Gabriel Yared score that lends woozy sensuality to this portrait of la dolce vita as a simultaneous reverie and nightmare.

As with Antonioni’s The Passenger, The Talented Mr. Ripley is an assumed-identity thriller with a heart full of existential dread and terror. “I always thought it would be better to be a fake somebody than a real nobody,” confesses Tom to the new object of his affection, Peter (Jack Davenport), but Minghella’s film contends that such transformation is impossible. Whether donning a guise like when he wears a borrowed jacket or a pilfered ring, or baring his true empty self, Tom is lost and alone, a cipher destined to fail at filling himself in with other people’s thoughts and feelings. He’s a black hole that fatally steals any light that enters his orbit, and in Minghella and Damon’s hands, he’s most scary for looking and behaving, at least on the surface, just like you and me.

That The Talented Mr. Ripley didn’t net any Oscars may simply speak to the uniquely bountiful excellence of that cinematic year. Still, two decades later, one also suspects it may have had something to do with its bone-deep bleakness about human nature, the viability of justice, and man’s capacity to change—a pessimism that’s all the more chilling for being wrapped up in a such a rapturously enchanting package.