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Better Late Than Never: 19 Must-See Movies from 1999

From 19 movie lovers to another, here are some of our favorites from 1999.
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By  · Published on June 12th, 2018

We get a lot of emails here at Film School Rejects, and while most of them are split pretty evenly between people curious if Kieran Fisher is a “real” person and others asking Christopher Campbell, Esq. for nudes, some are actually complimentary enough towards the site to count as fan letters.

One such example came to us recently from a young woman in the UK hoping to celebrate turning 19 years old with a writing project about movies released in 1999. Her plan was to watch or re-watch films from that year and then write about each of them whether she connected with the movie or not. As a fan of FSR and One Perfect Shot she asked if we could offer a few suggestions as to what we consider to be the must-see movies of 1999.

“Hi, I figure this email is a long shot but I’d really love your help. My name is Ellie, I’m 18, a complete film geek and I could not live without Film School Rejects or One Perfect Shot. I’m starting a project that involves me trying to watch new or rewatch 19 films from 1999 by the time I’m 19 on June 2nd and I would really love any suggestions that I can add to my list. I know its small, but this project means a lot to me and I’d love to complete it and write up about all of them, whether I’m passionate about them or whether I detest them. It would mean the world to get some help on this.

Thank you thank you thank you!

London, United Kingdom”

The smart, easy, and nice thing to do would have been for one of us to dash off a quick list of 1999’s best films so she’d have it in time for her birthday. Unfortunately, we here at FSR prefer to complicate things and miss deadlines whenever possible, so instead of a short list we’d like to present Ellie with 19 picks from 19 members of our team. Some might seem obvious, others less so, but it’s most definitely a broad spectrum highlighting not only our staff’s eclectic tastes but also the absolute wonder that is cinema’s breadth and scope.

We write about movies because we love movies (and because Disney pays so damn well for positive Marvel coverage, but that’s a bit off topic so forget I even said it), and we’re equally excited by any opportunity to share that love with others. There are so many amazing films out there, and like everyone else, we’re still discovering new favorites every day.

So happy belated birthday Ellie! We apologize for the tardiness of our reply, but hopefully you find something new to appreciate from our picks and that they add to your already growing love for the movies. (And, yes, we did add a bonus pick for an even twenty to get a jump on your 20th birthday…)

10 Things I Hate About You (directed by Gil Junger)

Perhaps the last great teen movie of the 20th century, 10 Things I Hate About You made its debut in 1999. It’s essential viewing for any rom-com fan, but especially for young women. Kat (Julia Stiles) is a badass feminist lead unlike many we see in romantic comedies who accepts an invitation to prom from class mystery man Patrick (Heath Ledger). There’s miscommunication, true love, and a Shakespeare enthusiast. The soundtrack is the perfect time capsule of 1999, but it still rocks today. It’s a fun and adorable movie I adored when I was nineteen! – Emily Kubincanek

All About My Mother (directed by Pedro Almodóvar)

Us film writers have a bad habit of using “melodrama” like it’s a dirty word. The thing is, melodrama is most often used as a crutch—blatant appeals to viewers’ emotions made in an attempt to distract audiences from other shortcomings. It takes a skilled filmmaker to remind us of how wrong we are in conflating melodrama’s potential with the underwhelming contents in which it is most often seen, and Pedro Almodóvar is perhaps the preeminent master of melodrama working today. Todo Sobre Mi Madre (All About My Mother) is stuffed to the brim with plotting straight from a soap opera, expertly condensing the twists and turns one might expect from an entire television season into less than two hours. Gorgeously vibrant and filled with innovative cinematography that will stick in your brain long afterward, the film is a much-needed reminder that melodrama and great cinema can absolutely be one and the same. And that you should always look both ways before crossing the road. – Ciara Wardlow

Analyze This (directed by Harold Ramis)

What is the best way to understand film genre? Apart from actually sitting down and immersing oneself in its finest examples, the answer is clear: genre parodies! An overlooked classic is Harold Ramis’ Analyze This. One sentence summary: Robert De Niro plays a mob boss and Billy Crystal is his psychiatrist. It’s a ton of fun! Also, it’s a thoughtful satire, one that raises deep questions about our understanding of masculinity, especially in films about Italian-American men. In Goodfellas, De Niro plays a mobster completely devoid of emotion; here, he plays one who struggles to admit he has emotions because he believes doing so would make him weak. It’s well-worth your time, plus, if you like it, there’s a sequel! – Will DiGravio

Audition (directed by Takashi Miike)

By the time you read this, Takashi Miike’s filmography will have surpassed 100 directorial outings and some change. The Japanese maverick is a workaholic who’s willing to make any project he gets offered, though when you look at the eclectic array of titles in his oeuvre, what you see is some of the boldest and most daring cinema of the last 20 years. Audition, which is based on Ryu Murakami’s novel of the same name, is one of his foremost masterworks, as well as an example of J-horror at its smartest and most sadistic. It tells the story of a widower who’s looking to get back into the dating game, but he gets more than he bargained for when he meets a woman with a mysterious past and a willingness to go the extra mile. Part romantic comedy, part stomach-churning nightmare, Audition serves as the perfect introduction to Miike’s demented world, and it’ll either make you want to delve in further or avoid it forever. – Kieran Fisher

The Blair Witch Project (directed by Daniel Myrick & Eduardo Sánchez)

Found footage movies get a bad wrap. Look, I get it. After the – ahem – foundational film The Blair Witch Project made its splash debut at Sundance Film Festival, screening at midnight to an unsuspecting crowd, studios every year have attempted to cash in on this low-cost way of filmmaking. But when done right, this POV format elicits a cinema verite quality that we so rarely see in the horror genre. And that’s what makes Blair Witch work so well. It just feels real. And in a time when the internet was just becoming what it is today, it was easy for the studios to really capitalize on that and make audiences believe that it was real. From the website that the filmmakers set up to the Sci-Fi Channel “documentary” The Curse of the Blair Witch that ran the week before the film released, they essentially made not only the first Augmented Reality game but also an immersive experience. Watching the film you feel like you are in the Black Hills Forest with Heather, Mike, and Josh slowly losing your sanity as the claustrophobic woods send chills down your spine. And when the woods finally come alive, the terror feels real. In a decade that was full of glossy excess, the simplistic DIY quality of The Blair Witch Project made it a breath of fresh air. This film didn’t have beautiful 20-somethings, pretending to still be in high school, running away from a hook hand or a ghost mask, this was a fear of the unknown. What’s right behind the door, or down that dark corridor. What we can’t even begin to comprehend, for fear we go mad. Often imitated, but never duplicated: The Blair Witch Project is real old-school horror. – Jacob Trussell

Dick (directed by Andrew Fleming)

After nearly 20 years, I still can’t believe Dick hasn’t become at least a cult classic. This movie has so many hilarious performances from its mix of Kids in the Hall and Saturday Night Live cast members, including Bruce McCullough and a not-yet-famous Will Ferrell as iconic journalists Carl Bernstein and Bob Woodward. Ryan Reynolds is here pre-fame, as well. The political satire mashed with teen comedy stars Michelle Williams and Kirsten Dunst on the edge of their transitions from child actresses to Oscar and Emmy worthy talents, and that’s a perfect spot for them to be in while they play bubbly girls in the midst, almost Forrest Gump-like, in one of America’s most notorious scandals. It’s a hip, lampooning introduction to the Nixon Administration and Watergate for young audiences with a wonderful portrayal of Tricky Dick by Dan Hedaya, and it’s a light and entertaining take on political corruption and the well-worn story of becoming disappointed with heroes and leaders. – Christopher Campbell

Election (directed by Alexander Payne)

Hear me out: Tracy Flick did nothing wrong. Over the years, Reese Witherspoon’s portrayal of an uncannily chipper, type-A teen who will stop at nothing to become student body president has been hailed as both a cultural icon and monstrous villain – but as a profoundly dorky and overachieving teenage girl who first saw Alexander Payne’s Election when I was Flick’s age, I’ve always felt a deep kinship with her. Matthew Broderick is disarmingly convincing as its (unreliable) protagonist, a beloved teacher who can only see Flick as a vindictive seductress after an affair with his married colleague (a situation we’d recognize today as statutory rape). In retrospect, it seems to occupy a strange in-between era of teen-media canon – its sour, biting portrait of high school politics takes after the pitch-black wit of Heathers, and yet its earnest idiosyncrasy also recalls later, weirder works like the great American Vandal. It’s the rare kind of comedy whose sense of humor is dazzlingly sharp and yet never feels mean-spirited. – Aline Dolinh

Eyes Wide Shut (directed by Stanley Kubrick)

Stanley Kubrick’s final film is a salacious peekaboo exploration of the sexual desires hidden within the minds of our significant other. We recognize the deep, dark secrets that lurk inside our own fantasies, but we dare not ask our partners what delights they crave. What’s the password? You do not want to know. Eyes Wide Shut peels the curtain back on the lust that fuels humanity. The film is made all the more dangerous by casting real-life married couple (at the time anyway) Tom Cruise and Nicole Kidman in the roles of the husband and wife reeling from the revelations laid bare after one admits their carnal wants. Their bedroom confrontation is an exposed vein that the audience both recoils from and salivates towards. We should not be privy to such horrendous intimacy. Kubrick’s passing and the prudish controversy surrounding the centerpiece orgy marred the initial response to the film. The longer I’ve sat with Eyes Wide Shut, the more time it has wormed its way into my relationships. Don’t wonder what’s going on in your lover’s head. Ask. Or suffer the torment. – Brad Gullickson

Fight Club (directed by David Fincher)

Before it became a stereotypical Film Bro signpost, this fantasia of runaway masculinity was a pulsating, bloody, controversial revelation. An essential entry into the filmographies of Brad Pitt, Edward Norton, and Helena Bonham Carter, it was also the movie that gave David Fincher his biggest early push toward his current label as a modern auteur filmmaker. Love it or hate it, Fight Club is a pop cultural touchstone, referenced for its quotable dark humor, brutal offhand violence, anti-Capitalist ideology, and above all else, its wildly surprising ending. First and foremost, though, I think Fight Club is an example of what filmmaking can look like at its most technically brilliant. It was the movie that made me fall in love with the aesthetic side of cinema, the technical aspects which separate film from other mediums of storytelling. As with Fincher’s later works, Fight Club makes use of sounds and sights, colors and cuts that flow seamlessly together, fluid and visually dynamic, to create a rich and distinctive moviegoing experience. – Valerie Ettenhofer

Galaxy Quest (directed by Dean Parisot)

1999 was a simpler time on the verge of being more complicated. It undeniably had its eye to the future, but its special effects and grasp of a swiftly changing technological landscape haven’t all aged amazingly. Galaxy Quest actually holds up surprisingly well, but it does make for interesting viewing 19 years later. In 1999 the internet was still a new phenomenon, not yet a place where everyone and their dog had an opinion on your favorite sci-fi show. The film’s main plot, that an alien species have mistaken a tv show for reality, is inherently clever and funny, but seen from 2018, when all-consuming fandom is more visible than ever, it doesn’t feel quite so… otherworldly. That’s what makes it obligatory viewing for the end of the millennium — now officially older than its long-canceled titular show, it offers a prescient view of the world that it almost certainly didn’t intend. It’s a time capsule of accidental speculation. It’s also a fun space adventure with a lot of heart and Alan Rickman, so if you’re not in the mood for reflecting on how the world has changed drastically since your birth, you can still have a great time. – Liz Baessler

Girl, Interrupted (directed by James Mangold)

There truly aren’t many films exploring the motives and psyches of teenage girls, but alongside other 1999 releases such as 10 Things I Hate About You and The Virgin Suicides, Girl, Interrupted furthered the presence and dimensions of young women on-screen. In classic Winona Ryder style, she undertakes the role of an interesting, intellectual, and misunderstood adolescent, namely Susanna Kaysen, an eighteen-year-old who has found herself admitted to a mental institution following an overdose. She finds the women around her (an incredible supporting cast in the form of Brittany Murphy, Elisabeth Moss, and Clea DuVall) both relatable and frightening, revealing the inner prejudices she holds within herself. The real challenge Susanna faces, however, is the charisma and allure of sociopath Lisa Rowe (Angelina Jolie’s Oscar-winner, and an icon on every teen’s Tumblr dashboard circa 2012). Underneath the powerhouse cast and vivid identities, however, is a focus on mental illness and coming-of-age that makes Girl, Interrupted a seminal piece for anyone trying to navigate their place in the world. Susanna is the narrator of the story in place of the audience’s inner monologue, skipping with us through the highs, and tugging us out of the lows. It shows, frankly, that with therapy, recovery is possible. It also emphasizes the importance of friendship and the solidarity of women, providing a depiction of troubled teenage years with an absorbing and truthful force. – Anya Hudson

The Iron Giant (directed by Brad Bird)

When Brad Bird’s directorial debut about a boy and his giant robot from outer space hit theatres on August 6th, 1999, it was a critical success. But Warner Brothers hadn’t had the first idea how to advertise it, and it opened in ninth place at the box office. And in all fairness, The Iron Giant doesn’t exactly fit into a marketable mold. That’s one of the film’s strengths. It’s based off a children’s story that Ted Huges wrote to comfort his children after the suicide of his wife, Sylvia Plath. It’s a Norman Rockwell-inspired political parable about a young boy befriending a metal monster who, despite his programming, doesn’t want to do harm. It had something to say about fear-mongering, violence betting violence, and the cost of peace—and it said all these things without talking down to young viewers. At its core, The Iron Giant is a story of empowerment, not as myth or destiny, but as a choice. You are who you choose to be. You can be gentle, you can defend, and you can be kind. You can be superman. – Meg Shields

Magnolia (directed by Paul Thomas Anderson)

Magnolia is significant in the 1999 canon for several reasons. It is arguably Paul Thomas Anderson’s best film. It has an ensemble cast that rivals some of the best actors and actresses of our time. And frankly, it contains one of the best performances from Tom Cruise. That alone would be a feat, but Magnolia is an untraditional epic that proves that nothing is written in stone. Anderson uses a short story to present audiences to the idea of strange phenomenon. An unsuccessful suicide turns into a murder by the most unlikely circumstances. That is the theme that runs through Magnolia, unlikely circumstances. Donnie Smith (William H. Macy) was a former quiz show winner whose moment of fame passed him by. The man who hosts that show, Jimmy Gator (Philip Baker Hall), has his own issues as he is slowly dying from cancer. And these two are connected to other members in the cast through coincidences. Anderson has waned back and forth on whether Magnolia is his masterpiece, but regardless of opinion, there is no denying the power of the film. Add in an iconic score by Aimee Mann — and did I already mention Tom Cruise’s performance? — and you have a movie experience quite unlike any other. – Max Covill

The Matrix (directed by The Wachowskis)

Notice how in almost every action movie there will be a slo-mo fight sequence where the protagonist is dodging bullets left and right? You can thank 1999’s The Matrix for that. Though, admittedly, later films may not exactly do it justice. Moving past those iconic visual effects (known more familiarly as “bullet time”, undeniably made most famous by The Matrix though it can be found in its predecessors) this movie is a wild ride that defined the action genre for years to come. The use of sophisticated fight scenes, heavily featuring a martial arts fighting style as per its Hong Kong cinema influence, along with incredibly complex and unique worldbuilding, The Matrix has firmly secured its spot in pop culture legend. What’s more, Keanu Reeves shines as hacker-turned-rebel against the machines, adding sci-fi badass to his already notable film career. His journey as Neo takes you from sympathizing with his 9 to 5 struggles (a good juxtaposition, as the side gig as a career cyber-criminal was probably less relatable) and seeing apart of yourself in a character going through the gray-tinged motions of a salaryman, to wanting to be him. Who wouldn’t want an alluring, mysterious stranger to plunge you into the realities of a dystopia, introducing you to a cyberpunk cult who gives you the choice to change your perception of the world forever? It seems much more appealing in The Matrix, I promise. The Wachowskis’ most famous achievement, this is a film much better viewed than dissected, particularly at the risk of revealing an amazing semi-plot twist. It’s more than just a pop culture phenomenon, still able to stand tall in 2018 as the perfect combination of action film technique and sci-fi storytelling prowess. While the gothic, cyberpunk look of the costumes and character style may admittedly date itself, the core and general appeal of the movie hold strong. Where else can you find Reeves entering a technological-underworld, filled with the expected futuristic elements coupled with a grungy exterior⎯ while also battling cryptic agents and practicing kung-fu. – Kendall Cromartie

The Mummy (directed by Stephen Sommers)

Two sequels, four Scorpion King spin-offs, and an ill-fated reboot may have diluted the Universal Mummy brand, but Stephen Sommers’ original summer blockbuster is still as ruggedly charming as its lead. Brendan Fraser is at the peak of his dopey charm here, and Sommers rips off Indiana Jones with freewheeling ease, forgoing scares in favor of all manner of swashbuckling adventure, complete with a climactic sword fight with an undead army. There’s no sweaty cinematic universe-building to be found in The Mummy, just good old-fashioned grave-robbing fun. – John DiLillo

Peppermint Candy (directed by Lee Chang-dong)

There are plenty of light and fluffy movies I love, both from the US and elsewhere, but my heart belongs to darkness. (On the screen at least… I’ll stick with light and fluffy in real life.) South Korean cinema is better than most at scratching this particular itch, and Lee Chang-dong’s beautiful but devastating look at his own country’s recent history does it in brilliant fashion. Like the more well-known Irreversible from three years later, Peppermint Candy magnifies the story’s drama and emotional effect by playing out in reverse chronological order. We start with a broken man screaming on a train track as the locomotive rushes toward him, and we work backward through his life to the young idealist he once was. It’s a personal tale of one man’s disappointment, but the events he experiences also tell the story of South Korea’s own growing pains as a young democracy. It’s a smartly crafted punch to the heart, and it’s one of 1999’s best films. – Rob Hunter

Ratcatcher (directed by Lynne Ramsay)

Too often in conversations of a year’s best films are international works forgotten. For this reason, if you’re looking at 1999 in movies, Scottish writer-director Lynne Ramsay’s feature film debut Ratcatcher is a must-see. The film is set in 1973 and tells the story of James, a young boy living with his family in a run-down housing scheme in Glasgow during the city-wide garbage strike, leaving the already dilapidated residential units in worse conditions ever. By exploring the minutiae of the sensitive James’ daily life, Ramsay creates a film that delivers an incredibly thoughtful and powerful meditation on ever-relevant themes of poverty, guilt, secret-keeping and human connection. – Madison Brek

Ravenous (directed by Antonia Bird)

It’s been a slow climb to respectability for Bird’s 19th-century cannibal classic. Universally panned on its release – the film was called a ‘stupid black comedy’ and ‘material that’s often better suited to a Monty Python skit’ – Ravenous has slowly risen in the esteem of horror fans and earned a spot as one of the better horror films of the last 20 years. And for good reason: not only does Ravenous feature the kind of onscreen talent normally reserved for high-profile chamber pieces, it also contains one of the most memorable soundtracks of any decade, a pop-infused cacophony of period instruments and chanting (co-written by Blur and Gorillaz frontman Damon Albarn). Equal parts black comedy and superhero-horror hybrid, Ravenous is the kind of movie that was meant to get better with time. Here’s to the cavalcade of anniversary pieces already scheduled for next spring. – Matthew Monagle

The Straight Story (directed by David Lynch)

There’s art-damaged David Lynch, there’s network TV David Lynch and even big studio David Lynch, but what if the best David Lynch is the one that Disney randomly bought at Cannes the summer of ’99 and which remains the director’s only G-rated entertainment? Shot along the route that notable Iowan Alvin Straight took by lawnmower to see his brother over in Wisconsin a few years before, The Straight Story tells this tale with the kind of look-in-your-eye sincerity that Lynch had for so long only been able to perform in various tediously ironic costumes. Richard Farnsworth, a stuntman who once played Matthew in Anne of Green Gables, is Straight, exalted here as an ordinary joe stubborn to the progress of time and old wounds. One finally triumphs over the other when Straight decides to reconcile with an estranged brother two states away, who appears, as-who-else but longtime chum Harry Dean Stanton. Because of Straight’s decimated vision, the local Man tells him he can’t drive and god knows no All-American will be caught dead on a bus in those 49 states, so Straight hitches up a lawnmower from the local John Deere affiliate and off he goes, with longtime Lynch collaborator Angelo Badalamenti scoring this to an ambient take on that era’s popular The Oregon Trail 3rd Ed.-music. What follows is an epic Odyssian tale that offers Oscar-nominated real pain and real country patois. It was perfect for the comedown from the summer of Woodstock ’99, and it’s perfect for right now, the clouds gathering and you can see them far-off if you look, before another summer of infinite bleakness. – Andrew Karpan

The Virgin Suicides (directed by Sophia Coppola)

Sofia Coppola is known for her vested interest in girlhood and female experiences, and she’s been committed to this since her debut film in 1999. The film is haunting and achingly beautiful in its depiction of the events that led up to the Lisbon sisters taking their own lives, all before they turned eighteen. It is intimate and empathetic, characteristics that Coppola frequently employs well, but unlike her other films that take the perspectives of her characters as they grapple with loss and disillusionment, The Virgin Suicides never fully breaks through to the Lisbon sisters, leaving them as mysteries without answers, asserting how difficult it is to know each other but how important it is that we try to. Every time I revisit the film I find a new detail that reminds me how much I love Coppola as a filmmaker and how grateful I am for her work. – Anna Swanson

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Rob Hunter has been writing for Film School Rejects since before you were born, which is weird seeing as he's so damn young. He's our Chief Film Critic and Associate Editor and lists 'Broadcast News' as his favorite film of all time. Feel free to say hi if you see him on Twitter @FakeRobHunter.