25 Best Movies of 1999, Ranked (2024)

Trying to single out just one year as the best in cinema history can be difficult, to say the least, and opinions will naturally vary when it comes to picking one year as a favorite above all others. Still, it’s possible to select contenders; those years that feel up there with the best, feeling particularly strong and jam-packed with noteworthy releases. One of these years, without a doubt, would have to be 1999.

It seems like there was something in the air for the final 12 months of the 20th century, as all sorts of great, groundbreaking, and varied movies were released during this time. What follows is an attempt to highlight the best of the best from the year in question, starting with some very good movies from 1999 and ending with the all-time greats that were released in that very year.

25 '10 Things I Hate About You'

Director: Gil Junger

Heath Ledger had a good year in 1999, starring in the ever-popular 10 Things I Hate About You and similarly impressing in the lesser-known (but still very good) Two Hands, which is an entirely different movie and allows Ledger to give a very different performance. Still, he’s great in 10 Things I Hate About You in a romantic role, coming across as believably charismatic and undoubtedly cool throughout.

The film’s premise looks at young love and the struggles of dating while in high school, taking some clear inspiration from William Shakespeare’sThe Taming of the Shrew, successfully modernizing it all the while. It’s one of those 1990s movies that now feels nostalgic and comforting, given that, as of 2024, even those movies released at the very end of the 1990s are now at least a quarter of a century old. Hey, everyone’s got to feel old at some point.

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24 'Titus'

Director: Julie Taymor

10 Things I Hate About You was far from the only 1999 film to take something by William Shakespeare and do exceedingly interesting things with it, as the year also saw the release of the incredibly underrated Titus. It’s a film take on Titus Andronicus, one of Shakespeare’s darkest and most brutal tragedies (so that’s really saying something), and boasts a strong cast led by Anthony Hopkins and Jessica Lange.

It starts intense and just becomes more nightmarish and visceral as it goes along, following the titular character as he vows revenge following another character enacting vengeance upon him and his family, and so the bloody cycle goes. It’s an interesting and lesser-known Shakespeare work for starters, but the ferocity of the performances and the dazzling visuals courtesy of director Julie Taymor and cinematographer Luciano Tovoli really make Titus shine.

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23 'Office Space'

Director: Mike Judge

Office Space could well be the definitive movie about hating a job you have to work for a living, because it’s small-scale and laser-focused on such an idea, doing for office jobs what 1994’s Clerks did for customer service roles. It wasn’t a huge hit upon release, but has built up something of a well-earned cult classic status in the years (and now decades) since it first came out.

The plot of Office Space is simple, centering on a man (with some help from his friends) hitting back at uncaring and greedy upper management, with acts of rebellion inadvertently getting the protagonist promoted. It works well as a skewering of office politics and the tedium of life for otherwise well-off individuals during the 1990s; a decade when, in hindsight, a good many people seemed to have things pretty good, all things considered.

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22 'Audition'

Director: Takashi Miike

The films of Takashi Miike are generally not for the faint of heart, as this legendary Japanese director is no stranger to pushing boundaries and making uncompromising (not to mention genre-pushing) films. Audition is one of his best-known movies, and is up there with his greatest, too. Despite this, and despite it not being the most extreme of Miike’s films, it still feels like a stretch to call Audition anything close to approachable.

It's a slow-burn piece of horror, following how one man becomes enamored with an actress who comes to him for the titular audition, and the ways she ends up changing his life… certainly not for the better. The details are confronting and Audition is best experienced as one of those movies you should go into not knowing much about. Those with strong stomachs and a love of dark horror films will likely appreciate what they find.

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21 'Bringing Out the Dead'

Director: Martin Scorsese

Nicolas Cage has been in his fair share of bad movies, and similarly has appeared in various other movies that aren’t good, but prove bad in fun ways. He’s also capable of genuine greatness whenever he appears in a genuinely great movie, as shown by Bringing Out the Dead, which sees him teaming with Martin Scorsese, the latter of whom crafts one of his most intense films here.

Bringing Out the Dead follows a paramedic who’s going through a rough time, to say the least, with the film showing how his mind unravels over a particularly hectic stretch of time spent on the job. As far as stomach-churning psychological thrillers go, few push things as hard as Bringing Out the Dead does, with the screenplay (from Paul Schrader), direction, and lead performance from Cage all adding up to make the film an undoubtedly dizzying one.

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20 'The Blair Witch Project'

Directors: Daniel Myrick, Eduardo Sánchez

Putting a unique spin on the folk horror genre and changing horror movies forever in the process, The Blair Witch Project might feel overrated or kind of whatever nowadays in the eyes of some, but taking into account when it was made and what it achieved, it’s easy to admire. This is low-budget filmmaking with an emphasis on the “low,” given the handheld camerawork, loose dialogue, and intentionally rough feel.

But in the service of crafting a story that’s said to be about three young people who vanished one day, the realistic approach worked wonders, and was scary in a way that felt fresh and undoubtedly nerve-wracking. Waves of found-footage imitators in the years since The Blair Witch Project may have dulled its power, but its influence cannot be understated, nor can the fact that it genuinely scared people back in the day.

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19 'The Sixth Sense'

Director: M. Night Shyamalan

There are plenty of things that can be said about plenty of M. Night Shyamalan movies, as he’s a pretty distinctive director whose films often – though not always – prove polarizing, to say the least. But the film that made him a household name, The Sixth Sense, is generally regarded as being pretty great; so great, in fact, that most people will assume everyone’s seen it and won’t exercise caution regarding certain plot details.

To be as vague as possible, it is a supernatural thriller revolving around a young boy who claims he can see dead people, following the interactions he has with a psychologist brought in to deal with his unique condition. The Sixth Sense takes its time, at certain points, but it rewards patient viewers in more ways than one, and is one of those twist-heavy experiences that benefits from multiple viewings.

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18 'The Straight Story' ​​​​​​

Director: David Lynch

David Lynch seems drawn to making strange, surreal, dreamlike, and sometimes nightmarish movies, which makes the appropriately titled The Straight Story stand out. This is a film that could well feel strange because it isn’t as traditionally strange as the sort of thing you’d tend to expect from David Lynch, with fantasy/horror/thriller elements being absent, and the film instead being a moving character drama.

As far as the story goes for The Straight Story, it’s largely about one man traveling a great distance – by tractor – to visit an estranged brother whom he learns is in bad health. It becomes a film about one man’s determined journey, meeting unusual people and living life along the way. It’s a bittersweet movie and an ultimately charming one, and helps demonstrate Lynch’s surprising versatility as a filmmaker.

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17 'Tarzan'

Directors: Kevin Lima, Chris Buck

Regrettably, Disney’s Renaissance period did come to an end by the close of the 1990s, but the final film to fit within this part of the studio’s history, Tarzan, did signify things going out with a bang. It’s an animated retelling of a familiar tale, revolving around a boy who was raised by apes, and how, as a man, he became torn between continuing to live in the jungle and rejoining humanity.

It’s all very straightforward stuff, but the simplicity of the narrative isn’t a problem when it’s all so well-executed, and things never miss a beat. The animation stuns (and had some unlikely inspiration), and things are also elevated by the memorable music Phil Collins wrote for the film, doing for Tarzan what Elton John had (also successfully) done for 1994’s The Lion King.

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16 'Beau Travail'

Director: Claire Denis

Beau Travail is a definitive modern arthouse cinema classic, proving perplexing and difficult to watch at times, but inevitably being powerful and hard to shake once seen. It’s one of those films that’s naturally hard to describe, because it wants to challenge and explore unexpected themes, here mostly revolving around masculinity and the way certain gender expectations make life more difficult for some than needed.

The film does this in a somewhat obscure way, indeed, to the point where it’s not always easy to understand what Beau Travail as a movie is trying to say. However, it all comes together in a striking fashion by the end of the film (it helps that the final scene is also iconic), and in the end, that all shows that Beau Travail has staying power and, even if it’s hard to digest, everyone should seek it out and watch it at least once.

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15 'The Green Mile'

Director: Frank Darabont

Though it was never going to be quite as good as The Shawshank Redemption, which is Frank Darabont’s other iconic prison movie based on a Stephen King story, The Green Mile is still a hugely impressive achievement. Perhaps the emphasis should be placed on the “hugely” there, because The Green Mile clocks in at a little over three hours. It’s a daunting length on paper, sure, but the film earns such a runtime.

The setting is death row, with most of the characters being prisoners awaiting execution or prison staff assigned to oversee such individuals during their final days. It’s grim right from the start, and undoubtedly gets more soul-crushing as it goes along, but The Green Mile is inevitably successful when it comes to being moving. Not only are crime/drama/fantasy/mystery movies rare, but even fewer can claim to bounce between such genres while also being great. Thankfully, The Green Mile, though, is a great film.

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14 'Being John Malkovich'​​​​​​​

Director: Spike Jonze

What happens when you get Spike Jonze (best known for Her) and Charlie Kaufman (best known for writing Eternal Sunshine of the Spotless Mind) working together on the same movie? Admittedly, you get a couple of things… you get 2002’s Adaptation, but you also get the (arguably) even better Being John Malkovich, which is more relevant here on account of it being released in 1999 instead of 2002 and all.

It's hard to describe the premise of this one without coming across as borderline delusional, because the existence of a movie with a story that heavily utilizes a portal into the mind of John Malkovich sounds beyond strange, but here we are. Being John Malkovichdoes indeed exist, in all its funny, bleak, confounding, and mind-bending glory, and is worth watching purely because there’s nothing else out there quite like it.

Rent on Apple TV

13 'The Iron Giant'​​​​​​​

Director: Brad Bird

It’s easy to call The Iron Giant one of the best animated movies of the 1990s, but it’s also possible to label it one of the best movies – including live-action works – of the decade in question. The premise, which involves a young boy befriending something from outer space, might not sound too original, but it’s the execution that counts, not to mention all the other things The Iron Giant manages to do as a film.

There’s a personal and heartwarming story at the core of it all, with two characters eventually thrust into something unexpectedly huge, and the film itself appropriately ramping up in scale all the while. The Iron Giant works no matter where it chooses to go narratively and thematically, and it’s just a pure and moving film at the end of the day, not to mention one that’s very hard to resist.

Rent on Apple TV

12 'The Talented Mr. Ripley'​​​​​​​

Director: Anthony Minghella

Nowadays, viewers are a little spoiled for choice when it comes to adaptations of Patricia Highsmith’sTom Ripley novels, but 1999’s The Talented Mr. Ripley remains one of the strongest of the bunch. It adapts the novel of the same name, which was the first of Highsmith’s books featuring the character, and it’s the story that tends to get adapted the most (see also Purple Noon and the Netflix series simply titled Ripley).

This version of The Talented Mr. Ripley does the source material justice, and Matt Damon shines surprisingly well in the lead role. It’s a tense and hard-to-predict crime/thriller story, and a consistently suspenseful one from start to finish, all executed well enough that even those familiar with the original story might well feel their heart rate quickening as the film goes on.

Rent on Apple TV

11 'American Beauty'​​​​​​​

Director: Sam Mendes

Standing as one of the most popular Best Picture winners in Oscars history, American Beauty was hugely successful upon release and still mostly holds up well, even if it’s very much a product of its time. It taps into a sense of unease, boredom, and discomfort that other late 1990s movies (such as the aforementioned Office Space) also did, but there’s enough here to keep things gripping and at least somewhat relevant.

Parts of the premise might also be a hurdle, as might the fact Kevin Spacey plays the lead role… but regarding the former, it’s uncomfortable for a purpose, and regarding the latter… well, it’s admittedly hard to get around or handwave that. American Beauty is still successful; it can be harder to watch now, but that doesn’t necessarily make it bad. In fact, it’s still great, and most of it can be appreciated for what it achieved back when it was released.

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10 'South Park: Bigger, Longer & Uncut'​​​​​​​

Director: Trey Parker

Coming out at a time when South Park was still a relatively new show, all things considered, South Park: Bigger, Longer & Uncut took pre-established characters and an ever-expanding world and did wild things with them all. It’s a good deal more profane than the show had been up until that point, and arguably funnier, too. Also, it was a musical, and a surprisingly great one at that.

South Park: Bigger, Longer & Uncut has a story that involves the United States going to war against Canada because a movie from there has a bad influence on young Americans, but that’s just the start of it. It feels foolish to even try and explain what makes the film so biting, funny, and creative; the important thing is that it’s great, and can even be enjoyed by those who might not be particularly huge fans of the TV series.

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9 'The Insider'​​​​​​​

Director: Michael Mann

Michael Mann’s filmography is packed with plenty of great films, with many of his best-known being classifiable as crime/action movies. He has also made his fair share of biographical films, with The Insider likely being the best of those, partly thanks to the fact that it also works as a thriller, telling a true story with speed, efficiency, and suspense.

The true story at the heart of The Insider revolves around a 60 Minutes report that served as an exposé on the tobacco industry, depicting how it came to be and how being involved in such a story proved life-changing for those wrapped up in it. It’s fantastically acted by a cast fronted by Al Pacino and Russell Crowe, and is all pulled off in a way that’s surprisingly riveting; text on a screen can’t exactly do it justice.

Rent on Apple TV

8 'Fight Club'​​​​​​​

Director: David Fincher

You can’t really talk about great movies released at the tail-end of the 1990s without talking about Fight Club (first rule be damned). It’s one of numerous great films directed by David Fincher, but could well be his most iconic and influential, serving as a dark comedy, a psychological thriller, and a bleak satire on late 20th-century life all at once.

Fight Club is, on the surface, about one man breaking out of his comfort zone by getting involved with a vicious underground fight club, but it’s also about so much more, and stands alongside The Sixth Sense as a movie that can – and does – get spoiled pretty easily. All that’s to say that if anyone has somehow not seen Fight Club and isn’t aware of where the plot goes in its final act, they ought to stop whatever they’re doing and check it out.

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7 'All About My Mother'​​​​​​​

Director: Pedro Almodóvar

Some times of the year are positively drowning in movies made for – or revolving around – certain events/holidays, most notably Halloween and Christmas. Movies that feel appropriate for Mother’s Day don’t seem to be as common, but for anyone who wants something appropriate for the time of the year in question, All About My Mother has your back.

Typical for Pedro Almodóvar, All About My Mother expertly blends heart-wrenching drama and surprisingly effective comedy, here in the service of a story that’s about a mother coming to terms with the loss of a child, and reconnecting with the child’s father, who never knew she’d had a son. Naturally, it can be heavy-going at times, but there is a balance achieved with some humor, and Almodóvar approaches the premise with sensitivity, as always, making for a moving and emotionally rewarding film.

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6 'Boys Don’t Cry'

Director: Kimberly Peirce

In opposition to a dramedy like All About My Mother, there’s little to no levity to be found in Boys Don’t Cry, an unrelentingly grim – yet undoubtedly powerful – drama. It’s something of a coming-of-age film and is based on a true story, and follows a trans man attempting to find love and connection, only to also discover various intolerant people – some of them violent – that place his life in danger.

There’s an argument to be made that there are enough downbeat LGBTQ movies out there, and that such films shouldn’t feel like they have to be about tragic stories. It’s a fair argument, but so long as one knows what they’re in for, Boys Don’t Cry still feels vital and tremendously moving, being brutally honest about the consequences of hate and intolerance while also giving Hilary Swank the opportunity to shine in perhaps her most impressive performance to date.

Watch on Apple TV+