The 20 Best Movies of 1999 That Will Make You Nostalgic

• Directed by: Eduardo Sánchez, Daniel Myrick
• Starring: Heather Donahue, Joshua Leonard, Michael C. Williams
• Runtime: 1h 27 mins

Depending on who you ask, many have The Blair Witch Project as the top film of 1999 due to its intriguing storyline and cult classic status. Even if it's not automatically your number one, you can't deny the impact of the film which was directed by Eduardo Sánchez and Daniel Myrick, and starred Heather Donahue, Joshua Leonard and Michael C. Williams. Its plot? Three film students travel to a small Maryland town to collect footage about a local murderer known simply as 'Blair Witch.' In the process of collecting the footage they vanish, and the only thing left behind is the footage they've captured.

The Blair Witch Project received positive reviews from critics as a whole, with Roger Ebert stating in his July 1999 review: "The movie is like a celebration of rock-bottom production values--of how it doesn't take bells and whistles to scare us. It's presented in the form of a documentary." He continues: "At a time when digital techniques can show us almost anything, "The Blair Witch Project" is a reminder that what really scares us is the stuff we can't see. The noise in the dark is almost always scarier than what makes the noise in the dark." If you want real horror without the gimmicks, The Blair Witch Project is a film that delivers in that department.

• Directed by: David Fincher
• Starring: Brad Pitt, Edward Norton, Helena Bonham Carter, Jared Leto, Meat Loaf
• Runtime: 2hr 19 mins

It might seem cliche, but we've gotta do Fight Club next because, well, it's Fight Club. Frequent collaborators David Pincher and Pitt came together once more for this now-classic that was once very much criticized. In the film, a depressed insomniac (Norton) meets an eccentric salesman (Pitt), and together they develop a fight club where they battle against individuals who are dissatisfied with their lives as well. As we just mentioned, Fight Club was pretty much hated by critics at the time of its release, proven by a 1999 review written by Stephen Hunter of The Washington Post. "Is this the same as being a good movie? Well, not exactly, though the director, David Fincher, clearly thinks so. But it is the same as being a provocative experience that lights you up even as it brutalizes you. And I don't even like Brad Pitt very much," says Hunter, which goes to show you the general dislike of the film (and apparently Pitt as well) upon it's initial release.

Well Mr. Hunter, twenty-five years later, it appears as though David Fincher, Brad Pitt, and Edward Norton got the last laugh.

• Directed by: Lana Wachowski, Lilly Wachowski
• Starring: Keanu Reeves, Carrie-Anne Moss, Laurence Fishburne, Hugo Weaving
• Runtime: 2hr 16 mins

*Automatically tries to do Neo's backbend and falls over because I'm not coordinated or flexible enough.* You want to know what I love the most about The Matrix—a film that absolutely rocked my world as a child? That it was directed by two women (sisters actually). Us women frequently get underestimated in terms of what people believe we're capable of, and while we'll probably always have to deal with that in some capacity, things are a tad bit better than what they were in 1999. Yes, its two women who wrote and directed this epic sci-fi action film that sparked a cultural movement, and The Matrix was unlike anything previously ever seen before in the movie industry.

"Keanu Reeves makes a strikingly chic Prada model of an action hero, that the martial arts dynamics are phenomenal," said New York Times film critic Janet Maslin in her March 1999 review. She added: "The martial arts dynamics are phenomenal (thanks to Peter Pan-type wires for flying and inventive slow-motion tricks), and that anyone bored with the notably pretentious plotting can keep busy toting up this film's debts to other futuristic science fiction." Describing Keanu Reeves as "chic Prada model," was brilliant as well because he absolutely looked like those Prada campaigns from the late 90s.

• Directed by: Gil Junger
• Starring: Heath Ledger, Julia Styles, Joseph Gordon-Levitt
• Runtime: 1hr 37mins

10 Things I Hate About You is movie that gets heavily referenced on TikTok as clips frequently go viral—a testament to the film's longevity. A teen romantic film starring Heath Ledger, Julia Styles, and Joseph Gordon-Levitt, 10 Things I Hate About You is a classic flick about a girl (styles) who gets deemed as unattainable, due to her status as the "smart serious student." That all changes, however, when she meets a handsome boy (Ledger) that makes her let her guard down. The film catapulted Styles and Ledger into young Hollywood royalty, and was received well by critics. A July 1999 review by Peter Bradshaw, The Guardian's longstanding film critic, notes: "It’s the smartest, funniest and most likable film of the week and is, moreover, in the most charming and unselfconscious manner possible, a homage to William Shakespeare."

If you want a classic late 90s teen romcom, 10 Things I Hate About You checks all the boxes.

• Directed by: Paul Thomas Anderson
• Starring: Tom Cruise, Julianne Moore, Philip Seymour Hoffman, John C. Reilly, Jason Richards, William H. Macy
• Runtime: 3hrs

A favorite of many Tom Cruise lovers, in 1999, Cruise starred in the drama film Magnolia alongside Julianne Moore and Philip Seymour Hoffman, which was a multiple-plot story about a dying father, young wife, a police officer falling head over heels in love, a genius, an ex-boy genius, a gameshow host, and an estranged daughter who all end up together on a random day in San Fernando Valley. Multiple-plot stories don't really get done a lot anymore in the film world, making Magnolia worth rewatch (or a first time watch if you've never seen it before). At the time of its release, critics praised Magnolia for its acting and the first two hours of the film, but felt that last hour wasn't really necessary.

"At the very least, ''Magnolia'' is a showcase for some splendid acting. Its single biggest surprise is Tom Cruise in the role of a strutting, obscenity-spouting cult figure named Frank Mackey," states Janet Maslin in her December '99 review. "Also extremely memorable here are two other members of Mr. Anderson's evolving stock company, Philip Seymour Hoffman as a dying man's devoted nurse and caretaker and John C. Reilly as an equally compassionate policeman. In each of them there is the mixture of creeping despair and saving grace that are the best ''Magnolia'' has to offer," Maslin adds.

While Magnolia might be a bit too long for some, the acting alone makes it one of the top films of the year.

• Directed by: Renny Harlin
• Starring: Samuel L. Jackson, Thomas Jane, Saffrons Burrows, LL Cool J, Michael Rapaport
• Runtime: 1hr 45 mins

Oh we're putting Deep Blue Sea on here ladies and gentlemen, and our primary reason for doing so is because of that Samuel L. Jackson scene where his character Russell Franklin delivers an epic rant only to be swallowed by a shark before getting to finish. Russell Franklin may not have lived a long time, but he died a hero rightfully very upset over a shark haunting him and his crew, and that scene alone makes it iconic. Roger Ebert, however, didn't agree saying in his 1999 review:

"Its premise is that the shark brains have been increased fivefold, with a corresponding increase in intelligence, so that the sharks can figure out the layout of the station and work together to batter down watertight doors, swim down corridors, etc. The most obvious problem with this premise is that just because a shark is smarter doesn't mean it has more information; the smartest shark in the world would only know how to be a smart shark unless it had a way to learn."

Fair point, but we're still standing by our sentiments.

• Directed by: George Lucas
• Starring: Liam Neeson, Ewan McGregor, Jake Lloyd, Natalie Portman, Ian McDiarmid, Keira Knightley
• Runtime: 2hrs 11 mins

What's your favorite Star Wars movie and why is it Star Wars: Episode I – The Phantom Menace? Liam Neeson led the all star cast as Qui-Gon Linn, as loads of people flocked to theater to see the official return of the Star Wars saga. The start of a trilogy, Episode I – The Phantom Menace commanded over $1 billion at the box office, but wasn't exactly loved by the critics with a May 1999 Washington Post review stating: "The Empire strikes out. There's a disturbance in the Force called hype, and "Star Wars: Episode I: The Phantom Menace" doesn't begin to live up to its advance press. Even die-hard fans of the heretofore awe-inspiring saga are bound to be disappointed with this joyless, overly reverential and impenetrably plotted prequel"

Ouch, but we'll let you make the call on where you choose to rank it amongst Star Wars films.

• Directed by: Robert Iscove
• Starring: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard
• Runtime: 1hr 33 mins

Starring Freddie Prinze Jr., Jodi Lyn O’Keefe, and Matthew Lillard (Prinze Jr. and Lillard would later star together in the Scooby-Doo movies), she’s all that is another classic teen romcom from the late 90s where the hot shot popular guy (Prinze Jr.) gets dumped, and now has to redeem himself by finding a new girl (Rachael Leigh Cook) in time for prom season. There's fun in the plot, but there's more fun around the edges,” said a 1999 review by Roger Ebert. He adds: “Freddie Prinze Jr. I learn, is 23, and Rachael Leigh Cook is 20. Still, they have a charm in their roles, muted somewhat in Cook's case because the plot requires her to be sullen much of the time,” he says of the acting. Is She’s All That a little late 90s corny in retrospect?

• Directed by: Roger Kumble
• Starring: Reese Witherspoon, Ryan Phillippe, Sarah Michelle Gellar
• Runtime: 1hr 37 mins

Cruel Intentions is without a doubt one of the best movies to come out in 1999. Starring Sarah Michelle Gellar, Reese Witherspoon, and Ryan Philippe, Cruel Intentions may sound like the plot of a stalker murder mystery (perhaps the stalker part gets fulfilled), it’s just really about love, lust, and a guy determined to get into the pants of somebody who wants to remain celebrate because he views her as a “conquest.” There’s a lot of layers to Cruel Intentions though, and perhaps that’s why it's gotten the cult classic label. Upon its release, Cruel Intentions received mixed reviews from critics. “It's refreshing, after the sponge-brained teenage romances of recent months, to see the movie reflecting that cynicism--up to a point. It crash-lands with an ending of soppy moralizing, but until the end, it's smart and merciless in the tradition of the original story,” said Roger Ebert in his review.

Time has been kinder to Cruel Intentions though as it is much more appreciated now than it was in 1999.

• Directed by: Trey Parker
• Starring: Trey Parker, Matt Stone, Mary Kay Bergman
• Runtime: 1hr 21mins

1999 didn't just bring a string of romantic comedies and dramas, it also brought about a very cool animated flick—South Park: Bigger, Longer & Uncut—the South Park gang up to their usual shenanigans but in a movie format. The film brought about some criticism and offended a few people as is the usual South Park way, but delivered at the box office grossing $83.1 million worldwide where it grabbed the title of the highest-grossing R-rated animated film—a title it held for seventeen years. A June 1999 review from The New York Times said: "With eerily perfect timing, ''South Park'' addresses the current national debate about the Motion Picture Association of America's movie ratings and President Clinton's call for exhibitors to enforce them vigorously."

The review continues: "In its cheerfully smutty way it wants to clear the air of pompous, hypocritical rhetoric about protecting children from basic if unpleasant realities. Beneath the hilarity, the movie is a scathing social parable in which desperate, paranoid grown-ups who long for an impossibly sanitized environment go collectively crazy to the point that they're willing to bring on World War III." Hey, if there's one thing South Park is going to do, it's bring the controversy.

• Directed by: Alan Metter
• Starring: Mary-Kate Olsen, Ashley Olsen, Ethan Peck
• Runtime: 1hr 27mins

If Billboard Dad was the precursor to Mary-Kate and Ashley's 2000s dominance, then Passport to Paris is what officially kicked the iconic era off. One of the most entertaining and interesting factors of MK and Ash's 2000s films was the fact they traveled the world, and gave you a glimpse of what life was like in other places. Sure the movies had it's own separate storyline, but in the midst of what was taking place, they made sure to show you around. That meant a lot, especially for kids like myself who didn't have the benefit of traveling the world—you got to go with Mary-Kate and Ashley.

Passport to Paris took place in the beautiful city of Paris, and was about two teenage twins that felt stifled by their tour guide, so they decided to hit the city with two French boys instead. Great style, great aerial shots, great views of the city, and a glimpse into Parisian food and culture.

• Directed by: Phillip Noyce
• Starring: Denzel Washington, Angelina Jolie, Queen Latifah, Leland Orser, Michael Rooker, Luis Guzmán
• Runtime: 1hr 58mins

Denzel Washington and Angelina Jolie's The Bone Collector centered around the pursuit of a serial killer who's M.O. is to leave behind a small shard of bone extracted from each of his victims. In this,Washington portrayed a quadriplegic forensic criminology expert using his expertise to help a policewoman (Jolie) to help track down the killer before he strikes again. A thriller full of twists and turns, The Bone Collector actually wasn't very well liked by critics. "The Bone Collector" is assembled from off-the-shelf thriller contrivances, likable characters and utter absurdity, with one of those scores that's the musical equivalent of trying to scrape the burnt meat off the bottom of the pot: Unnngh! Unnngh! Unnngh! Its big romantic scene has the girl cop caressing the index finger of the boy cop, which is the only part of him below the neck that still has any feeling. Freud has a lot to atone for," said Roger Ebert.

That said, The Bone Collector, is a film that has been better received with time.

• Directed by: Alexander Payne
• Starring: Matthew Broderick, Reese Witherspoon, Chris Klein, Jessica Campbell, Delaney Driscoll, Marilyn Tipp
• Runtime: 1hr 45mins

There's no question the riveting Election was one of the most critically-acclaimed and well received movies of 1999 (it earned Alexander Payne Oscar nomination for Best Adapted Screenplay). In it, Broderick portrays a well-liked government teacher Jim McAllister, who takes notice of a student (Witherspoon) that uses tactics that aren't exactly ethical to get what she wants—including her desire to be school president.

"Election" is the satire of the season, a hilarious, razor-sharp indictment of the American Dream. More accurately, Alexander Payne's movie is about the way that dream plays in the head of one Tracy Flick (Reese Witherspoon), an over-exuberant sprite who is running for Student Council president at Carver High School with almost satanic single-mindedness. And in the tradition of such all-American sendups as "Nashville" and "Smile," "Election" probes the internecine politics swirling around a closed world to better diagnose the societal maladies beyond its walls," said a 99 review from The Washington Post, and 25 years later it's a film that continues to hold up.

• Directed by: M. Night Shyamalan
• Starring: Bruce Willis, Haley Joel Osment
• Runtime: 1hr 47mins

The Sixth Sense is one of the best Bruce Willis movies of all time. Period. Diving into the horror realm, The Sixth Sense chronicles a child named Cole (Joel Osment) who has the ability to see and communicate with the supernatural. Understandably, Cole is frightened about his abilities, and only trusts child psychologist Dr. Malcolm Crowe (Willis), but that comes with consequences for the both of them. The Sixth Sense commanded $672.8 million at the box office, and enjoyed by critics. "I have to admit I was blind-sided by the ending. The solution to many of the film's puzzlements is right there in plain view, and the movie hasn't cheated, but the very boldness of the storytelling carried me right past the crucial hints and right through to the end of the film, where everything takes on an intriguing new dimension," said Roger Ebert in his recap, and that is essentially the essence of The Sixth Sense.

• Directed by: Darren Stein
• Starring: Rose McGowan, Julie Benz, Judy Greer, Rebecca Gayheart, Marilyn Manson, Ethan Erickson
• Runtime: 1h 25mins

I know comedy is one of the genres 1999's Jawbreaker is classified as, but when my mother first showed this movie to me in 2004, I was creeped out so badly that I had a nightmare that same night. I'm an adult now, and I have yet to rewatch this movie despite that nightmare twenty years ago. Jawbreaker is not by any means a horror film, but there's just something about that's...disturbing. In fact, a 1999 review from The New York Times said:

"What poured out was a semi-satirical mix of pink-clawed viciousness and girlie preening, the essential ingredients in half the other teen-age movies around. Once again, the babes are hot-looking predators obsessed with cruelty, popularity and materialism, crushing all nerds and innocents in their way. But since Stein borrows as much from John Waters as he does from the nasty-schoolgirl classics ("Carrie," "Grease," "Heathers," "Clueless"), he opens his film with a half-jokey killing, too. That gives his version an extra touch of tongue-in-cheek malice and some timely references to the teen-horror romp."

Perhaps I'll toughen up and rewatch it one day, perhaps I won't.

• Directed by: Malcolm D. Lee
• Starring: Morris Chesnut, Taye Diggs, Malcolm D. Lee, Nia Long, Sanaa Lathan, Regina Hall
• Runtime: 2 hrs

The Best Man is hands down one of the best films of all time—not just of the late 90s and early 2000s—of all time, and it genuinely saddens me that we will probably never see anything like this again. Not only did you have a group of elite young Black actors in their 20s/30s that were all rising in their careers at the same time, but The Best Man is a film that gives you just the right amount of everything as you had an equal mixture of drama, comedy, and a pinch of shock factor. "Everybody knows the freaky happenings jump off at weddings. They are a ritual confluence of women in tight dresses, groomsmen on the make and Uncle Morris doing the electric slide. Drama, love and great sexpectations. And in the hilarious romantic comedy "The Best Man," add to the mix a few secrets better left untold – not to mention unwritten, unpublished and definitely unread by the groom," wrote Lonnae O'Neal Parker of The Washington Post at the time.

And that describes The Best Man beautifully.

• Directed by: Paul Weitz
• Starring: Jason Biggs, Chris Klein, Thomas Ian Nicholas
• Runtime: 1hr 35 mins

It's truly not the year 1999 without American Pie now is it? It's not 1999 without the four boys who made a pact to lose their virginity on their prom night now is it? Commanding $235.5 million at the box office, American Pie was a success when it came out in 1999, and continues to have a legacy to this day. Critics weren't exactly impressed though as a 1999 review from The Hollywood Reporter said: "This American Pie is the kind Mom never baked. A raucous, ribald teen sex comedy, the film should score with its target audience. But an R-rating might cut down on box office take if NATO is serious about policing the rating code. In any event, the film is mostly stale pie for anyone older than 25."

Ouch again, but once more—time has been the biggest test for American Pie—and its passed in our opinion.

• Directed by: Dean Parisot
• Starring: Sigourney Weaver, Alan Rickman, Tim Allen, Sam Rockwell, Tony Shalhoub, Justin Long
• Runtime: 1hr 42 mins

Blink once and you might actually think 1999's Galaxy Quest is Star Trek. That's what locks you in, and in actuality, Galaxy Quest is actually a spoof about a "Star Trek" group's effort to overcome the oppressive regime within their solar system, which makes its overall mission very much comparable to Star Trek. Helmed by Dean Parisot, and starring Sigourney Weaver, Alan Rickman, Tim Allen, Sam Rockwell, Tony Shalhoub, and Justin Long—the film got good reviews from critics at the time of its release.

"Galaxy Quest," a mischievous spoof of the "Star Trek" phenomenon, boldly goes where everyone has gone before. And has a swell time getting there. This affectionate space oddity sets a dead-on for the cheesy sets, ham actors and old-fashioned idealism that define the enduring TV series," said The Washington Post in its recap, and the film continues to live on 25-years later.

• Directed by: Roger Michell
• Starring: Julia Roberts, Hugh Grant, Rhys Ifans, Hugh Bonneville, Gina McKee, Emma Chambers
• Runtime: 2hrs 4 mins

Sigh. They just aren't doing romance films they used to back in the day. Starring Julia Roberts and Hugh Grant, many believe 1999's Notting Hill to be the top film of the year as it's about a London bookstore owner (Grant), who falls head over heels in love with a famous actress (Roberts) who visits his shop one day. Drawing in $363.8 million at the box office, Notting Hill was well-received by critics too with a May 1999 review from Ebert saying:

"Well, of course, the moment we see Julia Roberts and Hugh Grant together on the screen, we want to see them snoggling, but a romantic comedy like "Notting Hill" is about delaying the inevitable. After all, they live in two different worlds. Her character, Anna, is one of the most famous movie stars in the world. His character, William, runs a modest little travel book shop in London. We know they're destined for each other, but we're always quicker to see these things than the characters are." Notting Hill remains a must watch in the catalog of both Julia Roberts and Hugh Grant.

• Directed by: Andrew Fleming
• Starring: Kirsten Dunst, Michelle Williams, Dan Hedaya
• Runtime: 1hr 34 mins

Set in the year 1976, Dick starred Kirsten Dunst and Michelle Williams as two 15-year-old girls that accidentally find themselves in the middle of the infamous Watergate robbery. Now they've got to be kept quiet, and to keep from the speaking out on what they saw, Richard Nixon (Hedaya) appoints the two teens to become his personal advisers, which goes...exactly like how you would expect it to. "Pity poor Richard Nixon. Although he's not here to be kicked around by the press anymore, he is still an irresistible lightning rod for gleeful ridicule. In exaggerating Nixon's mannerisms, Hedaya has created the year's funniest film caricature. With his hunched shoulders, darting paranoid gaze and crocodile grimace, Hedaya's Nixon is the quivering, skulking embodiment of a single word: guilty," said an August 1999 review from Stephen Holden of The New York Times, and that about sums Dick up.