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12 movies of 1999 that redefined filmmaking

I recently came across an article on Indiewire where 1999 was called one of the most iconic years for film in the past few decades. Their article came days after the 20-year anniversary on The Matrix, which was released in the same year.

Upon further research, I found out that some of the most talked about movies by almost every millenial features in that list. Well, at least, the ones that are fresh in their memory. Every millenial was young and impressionable at that age when they first saw those movies and those films have left an indelible mark on this generation.

These films have impacted more than just the millenials. Both the ‘Baby Boomers’ and ‘Generation X’ were also immensely impacted by the movies that were released in 1999. These films not only ushered in a new era in filmmaking, they also changed the game when it comes to the way audience perceive different genres.

Like Indiewire says, the most heated debate amongst cinephiles is often: Which was the best year for film? And though their answers may vary, one thing everyone will agree on is that two decades ago, in 1999, the industry witnessed a tectonic shift. The industry was able to churn out path-breaking content and audiences responded favourably to both the variety and quality of the content.

Some of the movies released that year, like The Matrix, Fight Club, Election and American Beauty have become benchmarks according to which video-streaming platforms like Netflix and Amazon Prime measure the quality of their new movies. Not only that, their scripts and success often acts like a blueprint for the new movies that are now being made by both movie studios and video streaming platforms.

Here are some of most iconic films that released in 1999 –


Fight Club

Who can ever forget the first rule of ‘Fight Club’: nobody talks about Fight Club. And rule number two – You do not talk about Fight Club. But I will break these rules for the sanctity of this article. Never has a stand-alone movie so impacted both cinema and pop-culture simultaneously. With iconic dialogues, great acting and a convoluted script, this movie is a winner at almost every level. It is a cult classic that established its director David Fincher as one of the most iconic filmmakers of our time. It also ensured that its actors – Brad Pitt, Edward Norton and Helena Bonham Carter – became household names in the industry. But sadly, when this movie released in 1999, it was a commercial failure. And critics were divided in their views about the movie. The movie made $37 million at the box office against a budget of $63 million. Also, though many believe that Fincher wrote the script for the movie, the movie is actually based on Chuck Palahniuk’s novel of the same name.


The Matrix

20 years ago, Lilly and Lana Wachowski, Keanu Reeves, Carrie Anne Moss and Laurence Fishburne made a movie that turned an entire genre on its head. The Matrix ushered in a new era in filmmaking around the world. One that relies heavily on visual effects. It was also the first movie of the Matrix trilogy and launched a very successful franchise for Warner Bros. This cult-classic tackled the essential question: What will happen when man takes on the machines? The movie had a very hard to follow plot, with many of the cast also admitting to not understanding it. But people all over the world lined up outside cinema halls to witness this epic with its never-seen-before graphics and action sequences. The movie set a new standard of filmmaking in Hollywood with its lead characters dodging bullets in slow motion and antagonists body morphing. Fans of this classic believe that no movie, not even its sequels, have been able to replicate the magic of this March 31, 1999 release.



Peter Bradshaw, a film critic for The Guardian wrote about Magnolia – “(Magnolia) is an anthology of broken lives – each interleaving with the other in a lattice of ill omen and disquiet.” Paul Thomas Anderson’s epic follow-up to his immensely successful Boogie Nights (which established Mark Wahlberg in Hollywood) featured a star-studded cast that featured the likes of Julianne Moore, Philip Seymour Hoffman and Tom Cruise. The movie even went on to win the Golden Bear at the Berlin International Film Festival. The three hour long saga has an almost biblical finale which finally releases the viewers from the anxiety the director successfully builds. Seemingly, there is an inconsistency in the storytelling. But that just adds to the viewing charm of the movie. If you are unfamiliar with the work of Anderson, you will be stumped by his use of music and heavy dialogue to prop up his film. There is also an foreboding darkness to this film, something that is not present in Anderson’s other movies. Also, this movie was successful in establishing Tom Cruise as a bankable star in Hollywood. It also shows a vulnerable side to the action star that he rarely allows to be shown on-screen now.   


Star Wars: Episode 1 – The Phantom Menace

No year can call itself legendary without having a Star Wars releasing in it. History is witness that the release of a Star Wars movie is a pious event in any year. Though the seventh, eighth and ninth edition of the series have seen new directors, the original six were directed by avant garde director George Lucas. Lucas kicked off his Anakin Skywalker trilogy (Parts 1, 2 and 3) to the tune of $1 billion dollars worldwide, making it the third highest grossing movie ever released at the time. Star Wars is often considered a cultural phenomenon and not just a mere movie. However, ‘The Phantom Menace’ is considered the weakest link of the existing Star Wars franchise. Though it introduced us to some great characters like Liam Neeson as Qui-Gon Jinn, Ewan McGregor as a young Obi-Wan Kenobi and Natalie Portman as Queen Padme, it is widely considered the worst Star Wars of the entire series. Fan expectations were at an all time high after the smashing success of Star Wars VI: Return of the Jedi that released 1983 (In case you are confused here, fret not. Lucas first made parts 4, 5, 6 and then 1, 2, 3. Weird, right? Well, welcome to Lucas’ world.).   


10 Things I Hate About You

What happens when you mix Shakespeare’s prose with Heath Ledger and Julia Stiles’ acting chops? An updated version of the classic ‘The Taming of the Shrew’. Add a healthy dose of teenage romance, raging hormones and a cute Joseph Gordon-Levitt and you get the perfect romantic-comedy that has been produced by Hollywood in decades. Not only did it become a huge commercial success, it also redefined many elements of pop-culture. Though many rom-coms were made during that era, none of them were quite as accessible to the audience as this movie. And who can ever forget Ledger crooning Frankie Valli’s Can’t Take My Eyes Off Of You. The script of the movie is widely considered as a blueprint for modern films to make a rom-com, a genre that has all but died in recent times. Except maybe The Big Sick. And Netflix’s Set It Up. Though this movie largely owes its success to the 1995 classic Clueless, this movie is largely able to stand on its own. As compared to its competition, it was considered a thinking person’s rom-com and was not quite as perfect as Clueless. Julia Stiles and Heath Ledger, the lead actors, are weightier, more thoughtful actors than usually get cast in these kinds of roles.   


Eyes Wide Shut

The last film of legendary director Stanley Kubrick saw then power couple Tom Cruise and Nicole Kidman star in a baffling movie. According to Indiewire: “Eyes Wide Shut” captured the pop culture zeitgeist in 1999 as it marked Stanley Kubrick’s last movie. This movie, among others, is considered to be Kubrick’s career defining works and like the others it confounded audiences because its storyline is quite difficult to understand. Noted film critic Roger Ebert gave the movie a stellar 3.5 stars out of 4 and called it “an erotic daydream about chances missed and opportunities avoided.” The movie is a visceral outtake on a marriage that is filled in equal measure by passion and jealousy. Though most of the sequences in the movie keep the audience wondering if they are watching a daydream or a murder mystery unfold, the director makes sure to keep you absorbed till the very end trying to solve this conundrum. The one complaint many, including audiences and critics, have had with the movie in the past has been the movie’s ending. It ends with a reconciliation that many believed that could have been done away with. Like Kubrick’s USP, it could have been made into a loose end, which could have made the movie more intriguing. Sadly, Kubrick died days after submitting the final cut of this movie to Warner Bros.


Boys Don’t Cry

One of the most moving performances of not just her career but of almost the entire decade was Hillary Swank in the gut-wrenching movie ‘Boys Don’t Cry.’ Swank won her first Oscar in 2000 for her performance in the film. This film received a rare four out of four stars from Roger Ebert who said – One of the many virtues of “Boys Don’t Cry,” one of the best films of the year, is that never once does it supply the tiresome phrase, “I am a man trapped in a woman’s body.” Its motto instead could be, “Girls just wanna have fun.” Co-written and directed by Kimberly Peirce, the film was a huge financial win for Fox Searchlight, grossing $20 million worldwide opposite a $2 million production budget. One of the best aspects of the film is that the lead character, Swank, is not a transsexual, a lesbian, a cross-dresser, or a member of any other category on the laundry list of sexual identities; she is a girl who thinks of herself as a boy, and when she leaves Lincoln, Neb., and moves to the town of Falls City in 1993, that is how she presents herself. By then she has become Brandon Teena, and we must use the male pronoun in describing him. There is no preachy aspect to the film. It just wants to tell a story and not teach the audience a lesson.   



This Alexander Payne directed movie is a commentary on the life of a know-it-all student Tracy who wants to become student body president just so that she can claim every prize that her school has to offer. Payne earned an Oscar nomination for Best Adapted Screenplay thanks to his razor sharp black comedy “Election,” which was one of the biggest critical favorites of 1999. Roger Ebert gave the movie a 3.5 star glowing review and said – What sets this film aside from all the other recent high school movies is that it doesn’t limit itself to the world view of teenagers, but sees Tracy mostly through the eyes of a teacher who has had more than enough of her. With Reese Witherspoon’s determined and sweetly ruthless Tracy Flick, Payne also delivered one of the year’s most defining movie characters. The beauty of the movie is that even though it seems haywire in its execution, it is always very entertaining and never has a misstep. Matthew Broderick delivers another solid performance that cements his position as one of the most trusted stars of the 80s and the 90s. Ebert said: Now here is a movie that is not simply about an obnoxious student, but also about an imperfect teacher, a lockstep administration, and a student body that is mostly just marking time until it can go out into the world and occupy valuable space.


Sixth Sense

This supernatural thriller continued the excellent run of Horror’s banner year in 1999. This Bruce Willis and Haley Joel Osment supernatural chiller which made a household name out of M. Night Shyamalan, who went on to make Signs and Glass. But more than anything, this movie gave cinema one of its most classic twist endings. Something that has since been copied on numerous occasions and rarely successfully emulated. The movie became the rare genre film to break through at the Oscars, earning nominations for Best Picture, Best Director, and four other categories. Ebert gave this movie three stars but lauded the performances of Willis and Osment: Haley Joel Osment, his young co-star, is a very good actor in a film where his character possibly has more lines than anyone else. He’s in most of the scenes, and he has to act in them–this isn’t a role for a cute kid who can stand there and look solemn in reaction shots. There are fairly involved dialogue passages between Willis and Osment that require good timing, reactions and the ability to listen. Osment is more than equal to them. And although the tendency is to notice how good he is, not every adult actor can play heavy dramatic scenes with a kid and not seem to condescend (or, even worse, to be subtly coaching and leading him). Willis can. Those scenes give the movie its weight and make it as convincing as, under the circumstances, it can possibly be.


American Pie

In all fairness, I believe American Pie’s biggest contribution to cinema, especially Hollywood, is that it ushered in the genre of ‘sex comedies.’ Even Roger Ebert, who was not a big fan of the genre, gave the movie a three star review. In his review he pointed out something that was on the minds of all the viewers – “American Pie” is a comedy about four high school senior boys who make a pact to lose their virginity before the end of the school year. This alone makes it almost touchingly old-fashioned; I did not know Hollywood still permitted high school seniors to be virgins. The movie was equally about sex as it was about friendship and boys overcoming the fear of inexperience and achieving emotional and psychological maturity. However, one of the best things Ebert pointed out while he was reviewing this movie was: Teenagers used to go to the movies to see adults making love. Now adults go to the movies to see teenagers making love. Given that he wrote this review in 1999 is a big deal. This movie, in a way, changed the perception of sex in Hollywood. That and it gave birth to a slew of sex comedies in Hollywood which featured some of our favourite actors – like Ryan Reynolds in Van Wilder and Kal Penn in Van Wilder 2.


Cruel Intentions

Amazon Prime really won me over when they decided to stream Cruel Intentions. I really had no idea that this movie too was released in 1999. Starring Reese Witherspoon, Sarah Michelle Gellar, Selma Blair and Ryan Phillippe, this movie was all about kink while American Pie was all about sex. Witherspoon’s avatar in this movie was diametrically opposite to her role in Election. But it was just as endearing. Even though Ebert gave the movie three stars, he compared it to ‘Dangerous Liaisons’, which in itself is a huge win for this Columbia Pictures’ movie. The script of the movie is razor sharp till the very end where it is let down by ‘soppy moralizing’. Till then it is smart and merciless – much like the wicked 1782 novel by Choderlos De Laclos it is based on. Breaking away from the rom-com stereotype that was prevalent at that time, this movie was quite refreshing given its brash cynicism and ample sexualisation of its characters. Ebert notes in his review:  The plot’s Machiavellian emotional strategies remind us of the same story as it was told in Stephen Frears’ “Dangerous Liaisons” (1988) and Milos Forman’s “Valmont” (1989), but the much younger actors create the uncanny illusion of a high school production of a grownup play. Are teenagers capable of sexual strategies this devious and sophisticated? I doubt it; few adults are, and even those who qualify may simply lack the energy. This movie treated teenagers with a respect that movies till date were lacking of.


Special Mention – Notting Hill

“The truth is that I am just a girl, standing on front of a boy, asking him to love her.” And cue the tears. Nothing gets me in a teary mess like this scene in Notting Hill does. And quite frankly, nobody does romance like Hugh Grant and Julia Roberts do in this 1999 romance classic.The iconic pairing of Julia Roberts and Hugh Grant resulted in $364 million worldwide, a blockbuster gross considering the film cost $42 million to produce. And the support cast of this movie was just as stellar as the main cast was. And a special mention of Alec Baldwin who makes a blink-and-miss appearance in the movie.


American Beauty

I almost did not mention this movie given Kevin Spacey’s presence in this movie. But in all fairness, there is much more to this Sam Mendes classic than his performance. “American Beauty” was the critical darling of 1999, winning the Oscars for Best Picture, Best Director, and Best Actor (Kevin Spacey) the following year and becoming the rare adult drama to earn huge box office numbers ($356 million worldwide on a $15 million budget is mighty impressive). The film received the rare four star honour from Ebert (who if you haven’t figured out by now, is the greatest film critic of all time) and can best be defined a tragedy that is comedic at times. The movie is about a man who fears growing older, losing the hope of true love and not being respected by those who know him best. And if you can’t relate to all this, you got a lot going on for you. You should probably start your own cult. But the movie is relatable because it shows the inner conflict within a man who thinks he has fallen in love with a minor. Even though it sounds like Lolita, the truth is that it is nothing like the infamous book. The movie is rarely shocking, though its storyline is often borderline risque. There is a morbid satisfaction the viewer receives by the end of the movie. Like the lead actor, who loses all but his sanity by the end of the film, the viewer thinks there is hope in life after all.