What Should’ve Won That Could’ve Won: 1999

The Year: 1999
What the Nominees Were: American Beauty, The Cider House Rules, The Green Mile, The Insider, The Sixth Sense
Other Movies That Should Have Been Considered: This year is very frustrating for me. The internet (and even an actual print book entitled “Best. Movie. Year. Ever.: How 1999 Blew Up the Big Screen” by Brian Raftery) loves to claim that this was one of the all-time best years for American film. I just don’t see it. Most of the nominees are merely okay movies. As for non-nominees, it’s supposedly a shame that The Matrix wasn’t nominated? Really? When I saw it, I immediately tagged it as a recipe for creating psychopaths (nobody is real but you) and that’s proven to be very true. Fight Club has similar problems. Magnolia is a very good movie but it’s also a mess, where half the storylines don’t work as well as they ought. Eyes Wide Shut is a bit of a trainwreck. I enjoyed Being John Malcovich at the time but tried to rewatch it recently and couldn’t get through it because it’s just too self-consciously quirky. Election is brilliant, but its attitude toward child-abuse has aged very badly. Speaking of which…

What Did Win: American Beauty
How It’s Aged: Hoo boy. This very sympathetic portrait of a would-be child molester has aged even worse. Could you make an unproblematic movie about that subject matter? Maybe so, if you were very careful to get the tone right, but this movie doesn’t pull it off. And of course, given later allegations against star Kevin Spacey, it’s deeply ironic he got (and won an Oscar for) this role.

What Should’ve Won: The Talented Mr. Ripley
How Hard Was the Decision: Ultimately, there are only three unproblematic movies I love from this overrated year: Galaxy Quest, The Sixth Sense and The Talented Mr. Ripley. I rewatched the latter two to help make my decision and this one won (though I really enjoyed Sixth Sense and I do recommend it highly. Talk about a movie that rewards rewatches!)

Director: Anthony Minghella
Writer: Minghella, based on the novel by Patricia Highsmith
Stars: Matt Damon, Gwyneth Paltrow, Jude Law, Cate Blanchett, Philip Seymour Hoffman, Jack Davenport

The Story: After borrowing a friend’s blazer for a piano recital, young con man Tom Ripley gets a chance to go to Italy and try to convince a rich man’s son, Dickie Greenleaf, to come home. Instead, Tom kills Dickie and takes over his life, then has to tell many lies to try to avoid being discovered.

Any Nominations or Wins: Astoundingly, it didn’t get a Picture or Actor nomination, but it did get nods for Supporting Actor for Law, Adapted Screenplay, Score, Production Design and Costume Design. It won nothing.

Why It Didn’t Win: American Beauty oozed Profundity with a capital P (Oh, the plastic bag!) so this neo-noir beauty couldn’t compete, I guess. Still, it’s baffling that it got beat out for a nomination by weak fare such as The Cider House Rules.

Why It Should Have Won:

1. It certainly seems that the Academy has never loved Matt Damon (though 2026 may finally be his overdue year). This is one of multiple years he should have won the award, perfectly capturing both the psychopathic hollow soul and the achingly sympathetic underdog that form the warring cores of the character. Those two aspects shouldn’t go together, but Damon makes it work beautifully.
   
2. I’ve always said that the special ingredient to a great performance is to always give your actor a secret that is not revealed in the scene. Even better is when they have conflicting lies that the audience knows about that are about to smash together, and then we watch them acrobatically get out of it. Damon’s linguistic gymnastics are delightful and riveting.
   
3. At this point I’ve read the novel, seen the original French adaptation with Alain Delon (Purple Noon), seen this, and seen the excellent black-and-white TV adaptation “Ripley” with Andrew Scott in the role. I enjoyed all four, but this one is the best of them, because Minghella complicates the story more, twisting the many knives that are out for Tom at all times. (Most of the second half of the movie, featuring the Blanchett and Davenport characters, was added by Minghella.)
   
4. One of Minghella’s many changes was switching Dickey’s amateur dabbling from painting to jazz, which is inherently more cinematic (though the TV show got great fun out of Dickie’s terrible paintings.) You can tell that Minghella loves luxuriating in the late-night jam sessions, just as much as he loves to recreate midcentury Europe at its most gorgeous.
   
5. Speaking of gorgeous, is there any better casting as “the beautiful people” than late-90s Jude Law and Gwyneth Paltrow? They’re both great actors, but they also needed ethereal good looks for these part to work, and they certainly make the movie easy on the eyes.
   
   
   

Ah, 1999: Their slogan was “Don’t Be Evil.” Then they changed it.