Party like it’s 1999: 10 movies that encapsulate one of the greatest years for cinema

<span>‘A film about ideas’ … The Matrix.</span><span>Photograph: Landmark Media/Alamy</span>
‘A film about ideas’ … The Matrix.Photograph: Landmark Media/Alamy

In 1999, cinemagoers flocked to watch The Talented Mr Ripley, in which Jude Law smoked cigarettes in a lazily buttoned linen shirt. The same year, they could also watch the actor getting a socket stamped into the base of his spine so he could play a video game. In David Cronenberg’s Existenz, Law’s character is fitted with a gnarly looking “UmbyCord” and hooked up to a creepy, pulsing virtual reality game “pod” that mines his nervous system for data as he plays. While plugged in, the player is unable to take stock of the “real” world outside. “You won’t be able to stop yourself, so you might as well enjoy it,” says the game’s creator, a line that feels spookily resonant today.

I am certainly not the first person to notice that 1999 was a great year for film. At the time, Entertainment Weekly ran a piece with the headline: 1999: The Year That Changed Movies, declaring it the year “all the old, boring rules about cinema started to crumble”. It’s not that films such as The Virgin Suicides, The Sixth Sense and Fight Club are better than everything else that came before or after, but that 1999’s harvest was a bumper crop. That year’s freakish climate saw cross-pollination between Hollywood studios with money and independent-minded film-makers with vision. It was a period that saw cinema creating the culture instead of second-guessing it.

Twenty-five years on there is a renewed appreciation of this lightning-in-a-bottle moment for film. The Criterion Channel has launched a streaming collection celebrating 1999, while the film-maker Edgar Wright has declared it his personal favourite cinematic year. In the book Best. Movie. Year. Ever: How 1999 Blew Up the Big Screen, film journalist Brian Raftery describes it as “the most unruly, influential and unrepentantly pleasurable film year of all time”.

American Movie is a fascinating meta-commentary on personal branding in the pre-social media age

As the world hurtled towards the millennium, movie-making was animated by a naive, anything-is-possible optimism that feels genuinely alien today. And while in the 25 years since there has been increased visibility and opportunity for women and people of colour behind the camera, in other ways conditions have worsened. The stakes are higher, and the expectations are lower. A combination of less money, deteriorating labour conditions, degraded attention spans and risk-averse executives has meant that, even with today’s digital advancements, the landscape is considerably less hospitable to film-makers of all identities.

What’s striking about 1999 in particular is its variety. Weird, fun, thought-provoking movies were being made, and they were being watched, too. The following are not necessarily the 10 best or even the 10 defining films of 1999, but 10 great films that tell its story.

The Matrix

Dirs. Lily and Lana Wachowski
If 1999’s slate of movies tell us anything, it’s that the era’s film-makers were keen to show their range. Before The Matrix, the Wachowskis had made Bound, a sexy neo-noir. Their blockbuster follow-up is remembered for its groundbreaking visual effects (and much parodied “bullet time” sequences), but The Matrix is a film about ideas. The Wachowskis, who also wrote the film’s original screenplay, combined philosophy with wirework stunts, sci-fi with kung fu, Keanu Reeves’s hacker turned hero with a Black zen master played by Laurence Fishburne, and encouraged audiences to question the reality being shoved down their throats.

Eyes Wide Shut

Dir. Stanley Kubrick
It was supposed to be Kubrick’s comeback after a hiatus of more than 10 years. Completed just days before his death, Eyes Wide Shut is a relationship drama, a Christmas film, a blackly funny sex comedy, and proof that great film-makers are always capable of surprising us. It is unimaginable to think that a $65m movie about the sham that is the bourgeois marriage, starring the most famous married couple in Hollywood (the now-divorced Tom Cruise and Nicole Kidman), was even made. Certainly there’s been nothing like it since.

The Blair Witch Project

Dirs. Daniel Myrick and Eduardo Sánchez
After the glut of predictable, Scream-y teen horrors that dominated the 90s, a lo-fi found-footage movie about three film students trying to document the goings-on in a storied, haunted wood changed everything. No one thought a micro-budget film with no stars and a shaky handheld camera would make the box office top 10, let alone become its own cultural moment. Its marketing campaign cleverly worked to obscure the fact that the film was, of course, fiction, hoping to spook audiences further. They might not have bothered: even today, the film remains raw, plausible and absolutely terrifying.

The Best Man

Dir. Malcolm D Lee
In 1999, romcoms were still a bankable genre, and audiences were hungry for them. First-time director Malcolm D Lee had the knack, taking the wedding movie template and populating it with an all-Black ensemble cast. His cousin Spike Lee produced, and the film became a commercial hit. When Taye Diggs’s on-the-rise writer turns up to a university friend’s wedding, the gang are happy to be back together, until they realise his gossipy new “novel” is actually based on them. The film, which is warm, funny and sexy, was not pitched as a landmark moment in Black representation, meaning it was not pigeonholed as one, either.


Dir. Lynne Ramsay
In a year of films dominated by male film-makers, Ramsay’s directorial debut stands out. The Scottish director draws from her childhood in 1970s Glasgow in a film about a young boy coming of age among piles of fetid rubbish and a failing state (the film is set against bin strikes of 1975). Ramsay is utterly clear-eyed when it comes to the poverty James experiences, though its grimness is not her subject. She’s more interested in expressing the strangeness of childhood, and the loneliness of growing up; in a mouse that floats away on a balloon or beckoning golden fields.

American Movie

Dir. Chris Smith
A funny, odd and deeply personal movie set in rural Wisconsin, Chris Smith’s cult documentary might be written off as niche. Struggling film-maker Mark Borchardt is trying to make his magnum opus, but hubris, mounting debt and a drink problem are unfortunately slowing him down. Smith observes with a mix of admiration and pathos as the determined Borchardt begins work on a short horror film instead. But Borchardt is self-aware enough to understand the documentary is his showreel and that he must play the role of the auteur, in this fascinating meta-commentary on personal branding in the pre-social media age.

Beau Travail

Dir. Claire Denis
Plenty of films from 1999 examine the tight grip of machismo, but none with as much poetry as Claire Denis’ Beau Travail. Under the blazing east African sun, the French foreign legionnaires in her take on Billy Budd glisten. Denis highlights the beauty and strange grace of these men, creating a ballet of hard, sculpted bodies and tough-guy grunts, but asks what’s simmering underneath their dynamic, too, viewing the bitter rivalry between a gorgeous soldier (Grégoire Colin) and his jealous superior (Denis Lavant) with a piercing, feminine gaze.

10 Things I Hate About You

Dir. Gil Junger
Call it the Clueless effect: the late 90s saw various attempts to recreate the huge success of Amy Heckerling’s savvy teen movie Clueless. While Cruel Intentions restaged Dangerous Liaisons among New York’s private school elites, She’s All That riffed on Pygmalion, putting its Eliza Doolittle in dorky glasses. 10 Things I Hate About You is the era’s high-water mark. A witty, charming remake of The Taming of the Shrew with a tightly written script, it sees Julia Stiles’s spiky feminist Kat soften in the presence of a singing, dancing Heath Ledger, while still retaining a strong sense of herself.

All About My Mother

Dir. Pedro Almodóvar
In Pedro Almodóvar’s subversive and strikingly beautiful melodrama, a grieving nurse travels from Madrid to Barcelona, searching for the father of her dead son. There, she encounters a pregnant nun (Penélope Cruz), her son’s favourite matinee idol (Marisa Paredes) and a transgender sex worker (Antonia San Juan), all of whom explore their various maternal aches. The film was an arthouse smash that also won the Oscar for best foreign-language film, and cemented Almodóvar’s status as a major film-maker.


Dir. Paul Thomas Anderson
Should we give great auteurs carte blanche to make whatever the hell they want? In 1999, Paul Thomas Anderson was given $37m to make Magnolia, significantly more than the $15m budget of his previous film Boogie Nights. He spent it on a three-hour epic with a sprawling, Short Cuts-style ensemble cast, a karaoke interlude set to an Aimee Mann song and a literal storm of frogs. Anderson would learn to rein in the excess in his subsequent films, but this one stands out for its audaciousness, which feels very much of its time.