With the number of original movies that get greenlit by studios decreasing year to year, 1999 featured possibly the most groundbreaking original movies and adaptations of novels ever made. The year was the apex of all these mid-90s wunderkinder – David Fincher, Paul Thomas Anderson, Charlie Kaufman – who could seemingly do no wrong.
Movie studios were throwing blank checks at these young auteurs, and the filmmakers delivered the goods. On the other side of the coin, there were seasoned filmmakers who influenced these young directors also putting out their best work in years, and together, these guys created the most envelope-pushing year in American cinema ever.
10 Galaxy Quest
Galaxy Quest is one of the first great meta comedies. Parodying Star Trek, the movie follows a bunch of actors who star in a Star Trek-like TV show and are visited by real aliens seeking help.
The movie is hilarious and given that it fails to get the credit it deserves, it has become one of the great forgotten 90s gems, and it also sees Rainn Wilson in his first-ever movie role.
9 Fight Club
Despite being so universally acclaimed now and being in the IMDb top 10 movies, Fight Club is one of the surprising box office flops, as it bombed upon released and was even scathed by critics.
The movie was way ahead of its time, as it was battling toxic masculinity long before that was even a phrase, and it posed a ton of philosophical questions that viewers still haven’t recovered from. As the movie is based on the Chuck Palaniuk novel of the same name, it’s one of the few movie adaptations that’s actually better than the source material.
8 Eyes Wide Shut
Being the last movie of Stanley Kubrick’s before he passed away, he didn’t stray too far from his usual unpredictable style with this erotic thriller. With erotic thrillers being such a common genre in the 90s, Eyes Wide Shut is the one that would end them all, as it’s an epic story about a secret society that provides absolutely no answers.
The movie leaves viewers exhausted as they try to comprehend what they’ve just watched, and just like the best Kubrick pictures, it had fans theorizing for decades now. Curiously, it’s also one of Martin Scorsese’s favorite movies of the 90s.
7 The Talented Mr. Ripley
Right at the height of Matt Damon’s fame, The Talented Mr. Ripley came at the very end of 1999, and as the year was full of incredible psychological thrillers, it was able to squeeze out one more.
The movie follows a stranger who charms his way into the life of a very socially active and wealthy American living in Italy, only to attempt to steal his identity. It’s a shocking movie and it looks stunning, as the panoramic vistas of Italy have never been presented this way in a Hollywood movie ever before.
6 South Park: Bigger, Longer, & Uncut
South Park is not just one of the funniest animated shows on TV, but one of the greatest TV series, period. Matt Stone and Trey Parker did the impossible, which was to make a movie that was on par with the series, if not better.
The jokes are more vulgar, the narrative is more controversial, and there are a ton of great musical numbers that rival those of the show. South Park: Bigger, Longer, & Uncut changed comedy in movies forever and holds a legacy that few other comedies do.
5 The Matrix
There might be a few CGI shots that don’t hold up in the movie, but The Matrix amazingly balanced thought-provoking philosophical ideas and high octane action in a way that actually makes sense.
And though the ideas present in the movie are heavy, they are delivered in such a clear and concise manner, and it turned Keanu Reeves into the action star he is today. The sequels might not hold up, and whether or not we need a fourth movie is debatable, but the original remains the greatest action sci-fi movie of all time, and it was way ahead of its time with special effects too.
4 Big Daddy
With Adam Sandler becoming the most bankable comedy actor in the mid-90s, with movies like Happy Gilmore and The Waterboy, he reached his peak in 1999 with Big Daddy. The movie was derided by critics, but being one of the actors that critics hate and audiences love, there’s no denying the comedic prowess and surprising emotional side Sandler brings to the movie.
It was the first movie in Sandler’s resumé without a ridiculous premise (like playing a hockey player who becomes a golfer or a 20-something having to repeat first grade,) and though it might have inspired some not-so-great movies that came after, Big Daddy is a tent pole in 90s comedies.
3 Star Wars: Episode I – The Phantom Menace
The Phantom Menace has been on an exhaustingly sliding scale ever since it was released, as it was loved by critics and fans on opening weekend, and when the cinematic event was over, people saw it for what it is.
But now, with a generation of kids having grown up with it and the fact the sequel trilogy is now resented by many, The Phantom Menace is back in the conversation again. Audiences can hate it all they want, as there are a lot of things about the movie that don’t make sense, but there’s no denying the massive impact it had on the industry, and the pod racing is still incredible.
2 Being John Malkovich
From the celebrated screenwriter Charlie Kaufman, who bases the self-loathing protagonists on himself and puts them in bizarre, dreamlike situations, and director Spike Jonze, who is similarly strange in his style of directing, comes Being John Malkovich, the weirdest movie of 1999.
Being their first collaboration together, the movie is a work of art in both writing and directing, as it follows a former puppeteer get an office job, only to find a portal into the mind of real life actor John Malkovich behind a filing cabinet.
1 Magnolia
After Paul Thomas Anderson created Boogie Nights, which turned out to be a huge success, the director was given carte blanche to make whatever he wanted. And what he wanted to make was a 3+ hour melodramatic epic, which featured an ensemble cast of all-stars in a multi-stranded narrative where all their stories interweave.
On paper, it sounds like a hopeless task that was doomed from the start, but the movie is one of the most beautiful, life-affirming films ever made, and it even features a rare dramatic performance from Tom Cruise.
