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 Ledgerhad a good year in 1999, starring in the ever-popular10 Things I Hate About Youand similarly impressing inthe 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 in10 Things I Hate About Youin 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 fromWilliam 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.
10 Things I Hate About You
Watch on Disney+
Director: Julie Taymor
10 Things I Hate About Youwasfar 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 underratedTitus. It’s a film take onTitus Andronicus, one of Shakespeare’s darkest and most brutal tragedies (so that’s really saying something), and boastsa strong cast led byAnthony HopkinsandJessica 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 aninteresting and lesser-known Shakespeare work for starters, but the ferocity of the performances and the dazzling visuals courtesy of directorJulie Taymorand cinematographerLuciano Tovolireally makeTitusshine.
Buy on Amazon
23’Office Space'
Director: Mike Judge
Office Spacecould 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’sClerksdid for customer service roles. It wasn’t a huge hit upon release,but has built upsomething of a well-earned cult classic statusin the years(and now decades) since it first came out.
The plot ofOffice Spaceis 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.
Office Space
Watch on Hulu
22’Audition'
Director: Takashi Miike
The films ofTakashi Miikeare 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.Auditionis 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 callAuditionanything 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 andAuditionis bestexperienced as one of those movies youshould go into not knowing muchabout. Those with strong stomachs and a love of dark horror films will likely appreciate what they find.
Watch on Tubi
Director: Martin Scorsese
Nicolas Cagehas been inhis fair share of bad movies, and similarly has appeared in various other movies thataren’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 byBringing Out the Dead, which sees him teaming withMartin Scorsese, the latter of whomcrafts one of his most intense filmshere.
Bringing Out the Deadfollows 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 asBringing Out the Deaddoes, with the screenplay (fromPaul Schrader), direction, and lead performance from Cage all adding up to make the film an undoubtedly dizzying one.
Watch on Criterion
20’The Blair Witch Project'
Directors: Daniel Myrick, Eduardo Sánchez
Putting aunique spin on the folk horror genreand changing horror movies forever in the process,The Blair Witch Projectmight 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 sinceThe Blair Witch Projectmay have dulled its power, but its influence cannot be understated, nor can the fact that it genuinely scared people back in the day.
The Blair Witch Project
Rent on Apple TV
19’The Sixth Sense'
Director: M. Night Shyamalan
There are plenty of things that can be said about plenty ofM. Night Shyamalanmovies, 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 thrillerrevolving 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 Sensetakes its time, at certain points, but it rewards patient viewers in more ways than one, andis one of those twist-heavy experiences that benefits from multiple viewings.
The Sixth Sense
18’The Straight Story'
Director: David Lynch
David Lynchseems drawn tomaking strange, surreal, dreamlike, and sometimes nightmarish movies, which makesthe appropriately titledThe Straight Storystand 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 forThe 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.
The Straight Story
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, butthe simplicity of the narrative isn’t a problem when it’s all so well-executed, and things never miss a beat. The animation stuns (andhad some unlikely inspiration), and things are also elevated by the memorable musicPhil Collinswrote for the film, doing forTarzanwhatElton Johnhad (also successfully) done for 1994’sThe Lion King.
16’Beau Travail'
Director: Claire Denis
Beau Travailis adefinitive 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 whatBeau Travailas a movie is trying to say. However, it allcomes 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 thatBeau Travailhas staying power and, even if it’s hard to digest, everyone should seek it out and watch it at least once.
