Press "Enter" to skip to content

Best Year Ever: The 25 Best Movies of 1999 That Are Still Sitting in Your Parent’s VHS Collection in the Attic

Those of us old enough to remember the ‘90s look at them at the brief period of our lives where everything was okay. The economy was stable, the Cold War was over and the War on Terror was still a few years away. Things were good. So good that in 1999 we were gifted with one of, if not, the greatest years in cinematic history. Legends of cinema were still churning out classics, even if they’d be their swansong, exciting new voices were emerging, and new technology changed the way movies were made. Sure, “American Beauty” won most of the awards that year, but the Oscars are always kind of bullshit anyway. So with that said, here’s our list of the 25 best movies of 1999. We know we probably left some movie you personally like off or ranked it too low or high, blah blah blah. Whining in the comments won’t change anything.

25. Analyze This (dir. Harold Ramis)

In 1999, a mafia boss entered a psychiatrist’s office and after that pop culture was never the same. Of course we’re referring to this Harold Ramis film that began Robert DeNiro’s hit and miss shift into more comedic roles. This one has some great jokes and characters and we’d like to rank it higher, but at the same time, we can’t help but think that it was this that would cause DeNiro to later make “Dirty Grandpa.”

24. Cruel Intentions (dir. Roger Kumble)

You got to give it to whomever came up with the idea to take “Dangerous Liaisons,” move it to contemporary New York City, and then stack the cast with WB stars. It’s a concept just crazy enough to work and it did! We just guess that watching attractive, rich people play sick mind games with each other will always be entertaining in some way or other. Some definitely made bank off this one.

23. Beau Travail (dir. Claire Denis)

Are we including this one just to make ourselves look less vapid in our movie choices, probably. If subtitles and long meditations on colonialism, masculinity, and repressed sexuality aren’t really your jam, we do recommend you give this one a watch for a truly fierce dance sequence to Corona’s ‘Rhythm of the Night.”

22. But I’m A Cheerleader (dir. Jamie Babbit)

Until watching this one, we assumed that Melanie Lynskey was American. This coming-of-age drama invokes Pedro Almodovar and John Waters in its take on queer identity and romance during those miserable teenage years we’d all rather forget. Equal parts funny and heartfelt, unflinchingly raw in its depiction of sexuality, and a rare non-drag appearance by RuPaul as an ex-gay camp counselor.

21. Drop Dead Gorgeous (dir. Michael Patrick Jann)

It’s no easy task to take a genre like dark comedy and make it work with a PG-13 rating. But this delightful and nasty satire of small-town America and pageant culture is a funny twist on the teenage years that predates “Mean Girls,” does so in spades and is in many ways superior. Plus, any time Allison Janney plays a white-trash character, we’re on board.

20. Blair Witch Project (dir. Eduardo Sanchez)

Okay, we get this one is polarizing, but just hear us out on this. First of all, in 1999 the found footage horror genre was still a pretty new concept. Also, the use of unknown actors allowed them to push the notion that this was actually found footage. Sure, inevitably the secret came out, but it was in those early days of the internet before Twitter and Reddit ruined the moviegoing experience so it was fun while it lasted we guess?

19. Eyes Wide Shut (dir. Stanley Kubrick)

Kubrick’s final film was unfairly maligned at the time because cynical Hollywood executives decided to market this movie as more of a Tom Cruise-Nicole Kidman romantic drama. It’s not and the normies apparently weren’t ready for the psycho-sexual mystery among the wealthy that ensues. Thanks to this movie, the public is now more aware of the depraved orgies the super-rich have on the regular.

18. Bringing Out the Dead (dir. Martin Scorsese)

Martin Scorsese and screenwriter Paul Schrader reunite to make this psychological drama about an insomniac paramedic suffering from hallucinations of the patients he couldn’t save. If that fact isn’t enough to get you to watch this one, we have to question your taste in cinema and overall television. Fine, it’s probably one of Scorsese’s best soundtracks ever. Is that enough for you?

17. Go (dir. Doug Liman)

Upon its release, it was pretty easy to dismiss this one as yet another Tarantino knockoff of idiosyncratic pop-culture references and non-linear editing. And in lesser hands, it would’ve easily been just that. But director Doug Liman and a stellar cast, especially Sarah Polley, elevate this to a funny, quirky, and intense caper set in the late ‘90s rave scene we all kind of regret participating in. Put on a ring-pop and invite your old dealer over to wax nostalgic over this one.

16. The Sixth Sense (dir. M. Night Shylaman)

Three quotes probably sum up the nineties in cinema. ‘Show me the money,’ ‘Run Forrest Run’ and ‘I see dead people.’ With its unique premise and infamous twist, it’s no surprise this movie earned several Oscar nominations including Supporting Actor for Haley Joel Osment and Supporting Actress for the sublimely brilliant Toni Collete. Regrettably, for quite a few involved with this movie this was kind of where they peaked.

15. The Insider (dir. Michael Mann)

Remember all those god-awful anti-smoking PSAs, school assemblies, and videos we all were forced to suffer through in the early to mid-90s? Well, imagine now if those were directed by Michael Mann and starred Al Pacino and Russell Crowe as a journalist and former tobacco executive who team up to take down big tobacco. You wouldn’t be so quick to huck eggs at them or let the air out their tires in the school parking lot, now would you?

14. Run Lola Run (dir. Tom Tykwer)

It’s German! It’s got that insane techno soundtrack! It’s literally about a woman named Lola running! But, yet, it’s so much more than that…Honestly, by this point, we figure you know the premise. If you’re an older millennial, you and your equally pretentious college friends probably felt pretty high and mighty liking this one until that film student you were trying to impress mentioned they thought Kieslowski’s “Blind Chance” was better. Don’t worry though, this one slaps, they were just trying equally as hard to look cool as you were.

13. Ghost Dog: The Way of the Samurai (dir. Jim Jarmusch)

Look, we’re a punk site. We’re legally required to include a Jim Jarmusch movie on this list. While he has a dud or two (“The Limits of Control” or “The Dead Don’t Die”) Ghost Dog is not one of them. Once you take a second or two to look past Forest Whitaker’s cornrows, you get a slick action thriller that seamlessly brings together samurai and gangster flicks into this delightful, RZA scored movie. Also, bonus points for rapping mafiosos.

12. American Movie (dir. Chris Smith)

The ultimate ode to the DIY spirit and one man’s version of the American dream. Bills, setbacks, and severe lack of talent be damned, Mark Borchardt is hell-bent on getting Coven made. This movie has a heart and never judges its subjects, severely flawed as they are.If ever there were a movie that embodied the spirit of Punk Rock, it’s “American Movie.”

11. The Virgin Suicides (dir. Sofia Coppola)

The ‘90s did not start out well for Sofia Coppola and it seemed that the stain of “The Godfather Part III” would never come off. Or the even worse title of untalented Nepo Baby. However, the directing apple apparently doesn’t fall far from the tree as Coppola creates an almost dreamlike view of suburban life in the ‘70s, with a pretty kickass soundtrack too, that saved her from becoming the nineties answer to Pia Zadora.

10. South Park: Bigger, Longer, and Uncut (dir. Trey Parker)

If you’re an older millennial, you’ll remember 1999 as the year you bought tickets to see some other movie in order to sneak into either this or “American Pie.” While the latter hasn’t aged as well as millennials of a certain age, the complexities of Satan’s relationship with Saddam Hussein and hearing Eric Idle say “big floppy donkey dick” will never not be funny. Also, the title is a dick joke. And those are always fun.

9. The Limey (dir. Steven Soderbergh)

You probably know this one from the clip of an angry old English guy screaming “Tell him I’m fucking coming.” You probably laughed at it, cuz it’s an old English dude screaming he’s coming. Okay, now that that’s out of our system, let’s talk about “The Limey.” As the title would suggest, it’s about a limey who is hellbent on seeking vengeance against those he believes killed his daughter. A fairly straightforward plot that’s made infinitely more entertaining thanks to some amazing performances and Soderbergh’s direction. Plus, Peter Fonda as a sleazy record producer!

8. All About My Mother (dir. Pedro Almodovar)

Judging from the comments we get sometimes, we at the Hard Times often wonder if any of you can actually read, so we should warn you that this one has subtitles. If you’re able to get past that, you can enjoy this colorful, literally, Pedro Almodovar drama featuring pregnant nuns and lesbian actresses coming together to help a grieving Mom. It’s a celebration of women, mother’s, camp, and being queer. So you know, woke.

7. Office Space (dir. Mike Judge)

Overlooked in the theaters, this Mike Judge cult-classic found new life on video and helped prepare countless millennials for the soul-crushing drudgery of adulthood. Endlessly quotable, with a line for just about every social/professional situation you’ll inevitably find yourself in as you surrender your dignity, hopes, and dreams to pay the bills. Sure, your douchebag boss quoting it kind of detracts from the movie sometimes, but just picture Jennifer Aniston flipping off her boss and find your moment of zen.

6. Election (dir. Alexander Payne)

Reese Witherspoon’s career-defining performance that’s been misinterpreted by politicians like Elise Stefanik ever since. Seriously, every character in this movie is just plain awful and we’re so here for it. If the existential dread of the 2024 election is sending your sanity to the breaking point, consider this biting satire of American politics set against the backdrop of a high school election becomes more horrifyingly accurate with each passing year and just laugh at how fucked we truly are.

5. Toy Story 2 (dir. John Lassetter)

Next time someone asks you to name a sequel that’s better than the original, drop this one on them. Bringing back pretty much everyone from the first, plus some excellent new additions, this movie delightfully skewers obsessive collector culture and to maybe appreciate the things we have rather than whining about the things we don’t you greedy fucks. It brought the music of Randy Newman to a new generation which we won’t hold against it.

4. Magnolia (dir. Paul Thomas Anderson)

Cynical film school graduates will attempt to dismiss this movie as a “Short Cuts” knock-off, but they’re just jealous. Yes both movies are ensemble films about fucked-up Los Angelinos and, yes, both movies have Julianne Moore, but this movie has its own interesting take on life, love, death, and things left unsaid. Also, Tom Cruise gives the best performance of his career as an Andrew Tate-style pick-up artist. So good we almost forget all that Scientology stuff…

3. Fight Club (dir. David Fincher)

Discourse over the extremely online kind of ruining this movie for some aside, just remember that this movie was a satire of masculinity brought on by mass-consumerism and had more than its share of nudge-nudge wink wink homoeroticism. And released by a major studio and starring one of the most bankable movie stars in the world, no less. Plus, it predated social media so at least we were spared the hot-takes and pseudointellectual discourse every movie released these days triggers. Life was simpler back then.

2. The Matrix (dir. The Wachowskis)

1999 saw the return of the “Star Wars” saga to the big screen. Had someone told you then that a movie about artificial intelligence enslaving humanity starring Keanu Reeves would revolutionize cinema (for better or worse) and go on to become one of the most iconic movies of all time, you’d have been laughed out of the room. Yet 25 years later, one still wonders how it’s possible for one movie to kick so much ass.

1. Being John Malkovich (dir. Spike Jonze)

The ‘90s were an interesting time where a movie based solely on the premise of becoming actor John Malkovich got a mainstream release. Music video director and skateboard photographer Spike Jonze made the leap to cinema almost seamlessly when he teamed up with Charlie Kauffman for this oddball comedy. Quite frankly, we miss the days when studios still made quirky, weird comedies like this. Had this movie come out in the last five or so years, we’re pretty confident “Hey Malkovich, think fast” would have been an instant classic meme.