This is the fifth and final installment in my series on the cinema of the 1990s, attempting to define the style and themes of the decade through a sampling of 25 representative films. This article deals with the years 1998-99. For Part I (1990-91), go here. Part II (1992-93), here. Part III (1994-95), here. Part IV (1996-97), here. Thank you for joining me.

The Thin Red Line (1998, Terrence Malick, Director)

The 1990s was a critical time in popular memory of World War II. It’s the decade when the generation of veterans who served became “The Greatest Generation,” lauded in American culture as valorous heroes who fought selflessly to preserve democracy and save us all. A significant piece of myth-making that helped cement this vision was Steven Spielberg’s 1998 war film Saving Private Ryan, with which Terrence Malick’s The Thin Red Line is compared, usually unfavorably. The Thin Red Line, however, has aged extremely well; Saving Private Ryan has not. That’s because Mallick’s picture has nothing to do with “The Greatest Generation” and has no idea what that’s supposed to mean. As Sergeant Welsh (Sean Penn) remarks to his commander after an act of heroism that proves eventually meaningless, “The whole damn thing,” meaning the war, “is about property.”

The Thin Red Line is nothing less than the greatest war film ever made. It’s not really about storming Japanese bunkers or suffering soldiers or even the futility of war. It’s about moral chaos and moral injury. The fact that it happens during the Battle of Guadalcanal in World War II is almost incidental. Every single character in the picture, which has a stellar cast (John Cusack, Jim Cavizel, Adrien Brody, Nick Nolte, Jared Leto, John Travolta, etc.) is broken in some fundamental way. And most of them are beyond fixing. The film presents the tragedy of war not so much as loss and death, but as moral collapse for no good reason. And it’s a stunningly beautiful movie. It just doesn’t get better than this. It’s a masterpiece.

The Truman Show (1998, Peter Weir, Director)

Peter Weir’s The Truman Show is an interesting artifact of the 1990s because it asks a question that was provocative then, but very quaint now: what if every detail of your life was broadcast to the world, and you didn’t know it? In the film, Truman (Jim Carrey), your quintessential everyman, is the star of an unwitting reality show where his entire life is scripted and staged for a worldwide television audience that he doesn’t know is watching him. That was a mind-bending premise in 1998, but I say it’s quaint today in 2019 because now we’re all Truman. We put our entire lives on Facebook and Instagram, allow Google and Amazon to track our every move, and send our most private moments into the stratosphere daily. The only difference is that Truman never knew he was being watched; we know we are, but we’ve simply chosen to forget.

For this reason, The Truman Show doesn’t really hold up after two decades, but you can’t blame Weir for that. The film is entertaining and thought-provoking as it chronicles the process of Truman gradually coming to realize the nature of his existence, and ultimately confronting the director of the show and his life, Christof (Ed Harris). In 1998 the idea of technology and media reducing our personal privacy to nothing was still a scary one. Today we pretend it scares us, when we scroll through scolding news stories about personal information hacks and all the data Mark Zuckerberg has on us, but it really doesn’t. Privacy is an illusion. Given a choice between privacy and attention, we’ll choose attention almost every time. If the same film were made today with the same script, we wouldn’t sympathize with Truman’s plight–most of us would envy him. The world has gone way past the scenario of The Truman Show, but the film is still an interesting one to watch.

There’s Something About Mary (1998, Bobby and Peter Farrelly, Directors)

The Ben Stiller rom-com emerged as a potent force especially in the 2000s, but the Farrelly brothers’ hilarious There’s Something About Mary drew the blueprint. Though criticized for much of its humor being lowbrow and juvenile, this film, a surprise hit in 1998, is unabashedly and unapologetically funny while also being charming and heartfelt. It’s the story of an average guy (Stiller) who fell in love with the fetching Mary Jensen (Cameron Diaz) as a teenager, and who still has a crush on her 13 years later. He must fight off three other potential suitors (Matt Dillon, Lee Evans, Chris Elliott) in an increasingly bizarre cat-and-mouse game of misdirection, fraud and mistaken identity to win her hand.

There’s Something About Mary is not very deep, but it doesn’t have to be. It’s just fun. The jokes are dumb but they make us laugh, and everyone in the cast seems to be having a great time. A special stand-out is the very talented Lin Shaye as Magda, which has got to be one of the funniest performances of the decade. The Farrelly brothers came to prominence with Dumb and Dumber (1994), a pretty enjoyable light comedy, but There’s Something About Mary hums and clicks with a crackly comic energy that Dumb and Dumber couldn’t deliver. A great film is more than the sum of its parts. This is one of them.

The Talented Mr. Ripley (1999, Anthony Minghella, Director)

I didn’t like The Talented Mr. Ripley much when I first saw it in 1999, but 20 years later it’s one of my favorite films. I can’t account for the change except passage of time and the deepening of tastes. Based on a novel by crime writer (and notable misanthrope) Patricia Highsmith, The Talented Mr. Ripley shows us the titular character (Matt Damon), a penniless grifter of a young man who would “rather be a fake somebody than a real nobody.” When he hooks up with the rich but monstrously callow playboy Dickie Greenleaf (Jude Law) who’s wasting his father’s fortune in Europe, Tom Ripley is first dazzled, then envious, and finally he becomes Dickie–after murdering the real one. The layers of Tom’s deceptions build and the price of getting away with them gets ever higher. It’s a brilliant story, wonderfully and subtly told by Minghella’s writing and direction.

Set in the 1950s, The Talented Mr. Ripley is a lavish period piece as well as a tight thriller. We see villas in San Remo and landmarks in Rome, all perfectly period-appropriate; we visit a jazz club and a hotel suite in Venice, and even the RMS Queen Mary. All the supporting players, including (and especially) Cate Blanchett, Philip Baker Hall and the late James Rebhorn and Philip Seymour Hoffman, are at the top of their game. You don’t even have to be a Matt Damon fan–I’m not–to like him in the role of Tom Ripley. The picture is an example of the kind of sophisticated, thoughtful and yet still entertaining filmmaking that was possible at the end of the 1990s.

Eyes Wide Shut (1999, Stanley Kubrick, Director)

There are two kinds of Kubrick fans: the ones who love A Clockwork Orange and Full Metal Jacket and who can’t be bothered with the rest of his oeuvre, and those (like me) who can’t even sit through the aforementioned films, but love his “lesser” works like Barry Lyndon and this one. When I tell people Eyes Wide Shut is my favorite Kubrick film they look at me like I’ve got three heads. But it really is his crowning achievement. It’s a film so good, even Tom Cruise and his mono-dimensional character range can’t hurt it. As always, Kubrick knew exactly what he was doing with every frame. The moment he finished it, he died. There was nowhere he could go from here.

Based on an obscure novella written in the 1920s, Eyes Wide Shut is the story, mostly, of one wild night in the life of Manhattan doctor to the rich Bill Harford (Cruise), happily married, but who is shocked when his wife Alice (Nicole Kidman) tells him she almost threw him over for another man on a powerful sexual whim. Seeking adventure or perhaps recklessness, Harford winds up at some kind of bizarre masquerade orgy where New York’s rich and powerful go to be naughty. It’s not until the final scene and a line by Kidman where we doubt, after all the twists and turns of the last almost 3 hours, whether what we’ve seen “can ever really be the whole truth.” Kubrick plays with perception like nesting Chinese boxes, and with a gasp we, the audience, realize we’ve been played…but to what end? This is the terminal stage of the many subtle but wonderful things that were possible in 1990s cinema.

The 1990s were a decade like no other in American, world and cinema history. The things we saw at the movies during those 10 years were similar to what we had seen before and would see again, but not exactly like them. I’m not sure even at the end of this series I’ve gotten to the heart and soul of film in the 1990s. But thanks for coming with me on the attempt.

The screenshot from Eyes Wide Shut is presumably copyright (C) 1999 by Warner Brothers Pictures. I believe my inclusion of it here is permissible under fair use. I am not the uploader of any YouTube clips embedded here.