Examining 1999’s Culture Through Its Best Movies

Image result for the matrix 1999

In college, I had this class where we were supposed to learn about 19th century upper-class British culture by analyzing hundreds of paintings commissioned and hung in wealthy British estates during that time period. Some insights are surface level, like British people loved to hunt foxes. Other potential insights were hotly debated in class, like whether the presentation of women tended towards subservience or maternalism, or both, or neither, etc.

Either way, it was surprisingly fun, and I enjoyed sort of doing it again with Best. Movie. Year. Ever.: How 1999 Blew Up the Big Screen, by Brian Raftery.

The book examines dozens of 1999’s best movies, ranging from entire chapters dedicated to Blair Witch ProjectFight Club, and Sixth Sense, to brief interludes on American Pie, The Mummy, and Varsity Blues, to passing mentions of many more films. Between the stories, Raftery offers his own nuggets of speculations on the cultural, filmmaking, and business trends that caused 1999 to be such an incredible movie year.

To prove the book’s title, the following is a long, but by no means exhaustive list of the best, most famous, and most influential movies of 1999:

– Fight Club

– The Matrix

– American Beauty

– The Blair Witch Project

– The Talented Mr. Ripley

– The Mummy

– South Park: Bigger, Longer, and Uncut

– Office Space

– Magnolia

– Eyes Wide Shut

– Star Wars: Episode I – The Phantom Menace

– The Sixth Sense

– Toy Story 2

– Austin Powers: The Spy Who Shagged Me

– The Green Mile

– Boys Don’t Cry

– Any Given Sunday

– The Iron Giant

– American Pie

– The Insider

– Three Kings

– Girl, Interrupted

– Being John Malkovich

– Sleepy Hollow

– Election

– Pokémon: The First Movie

– Deep Blue Sea

– The Virgin Suicides

– Analyze This

– Rushmore

– Galaxy Quest

– The Thomas Crown Affair

– Varsity Blues

– Cruel Intentions

– 10 Things I Hate About You

– She’s All That

– Big Daddy

– Dogma

– Lock, Stock and Two Smoking Barrels

– Mystery Men

– Blast from the Past

– Following

– Go

– SLC Punk

Also, TV shows that began in 1999:

– The Sopranos

– The West Wing

– Family Guy

– Freaks and Geeks

– Batman Beyond

– Who Wants to be A Millionaire

– Roswell

– Courage the Cowardly Dog

It’s also worth listing the biggest news stories of 1999:

– The Columbine High School Massacre

– Impeachment of President Bill Clinton

– Height of the Dot-Com Bubble

– NATO bombs Yugoslavia

– Massive protests against the World Trade Organization (WTO) in Seattle

– JFK Jr dies in a plane crash

– Woodstock ‘99

– The build-up to Y2K

The following are my own insights on the major trends in 1999 based on the book’s descriptions, Raftery’s analysis, and my own speculation from seeing many of these movies. I’ll divide the sections between “Film Trends” and “Cultural Trends.”

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Film Trends

Big Studios Were Willing to Spend Big Money on Risky Ideas

As seen in: Fight Club, The Matrix, The Sixth Sense, Mystery Men, Galaxy Quest, Three Kings, Being John Malkovich, Magnolia, Eyes Wide Shut, The Iron Giant

This is the single most significant and succinct reason that 1999 was such an awesome year for films. Due to a combination of many seen and unseen factors (some of which will be elaborated upon below), the big film studios threw crazy amounts of money at risky projects, a significant percentage of which became classics.

In retrospect, it seems impossible that most of these movies were made at all, let alone with considerable budgets. (For comparison, Star Wars: Episode I had a budget of $150 million.) Eyes Wide Shut was given a budget of $65 million, The Matrix $63 million, Fight Club $60 million, The Sixth Sense $55 million, American Beauty $50 million cost $15 million, Three Kings $48 million, The Iron Giant $48 million, Galaxy Quest $45 million, and Magnolia $35 million. Even Being John Malkovich, which most studios thought was a literal joke, was given $13 million. All of these movies were based either on entirely original scripts or obscure literature.

The biggest budgeted movie of 1999 was Wild Wild West with $170 million. And even though it was backed by Will Smith, one of the biggest stars on the planet, it was pretty bonkers for a big studio movie.

Basically, if most of those movies were made today, they would either be pushed into tiny-budgeted Netflix/Amazon territory, or turned into tv shows. No major studio would give a movie like Fight Club (an inflation-adjusted) $92 million today.

Indie-Mainstream Hybrids Reached Their Peak

As seen in: All the same movies

According to Raftery, this trend started with Steven Soderbergh’s Sex, Lies, and Videotape in 1989. The Weinsteins at Miramax bought this no-budget indie at the Sundance Film Festival, threw it into theaters, and made $35 million. Then in 1994, the Weinsteins found Pulp Fiction and did the same thing, unleashing not only one of the best-reviewed movies of all time, but grossing an astounding $107 million (10th highest of the year) domestically. This triggered a massive drive of big studios descending on indie festivals (especially Sundance) to try to poach cool small films and flip them for prestige, awards, and box office profits.

This trend was so powerful that it began to reshape the filmscape. Slowly, indies became less… indie. Studios started greenlighting more-and-more small projects, basically trying to make their own indies. Naturally this drove up indie budgets, which led to bigger and better movies. Rising auteurs took advantage of the trend, often making their own tiny legit indies or even short films to catch the attention of the studios, and then getting small-mid level budgets to make their own movies.

1999 seems to be the year when this trend hit its peak. Indie-minded auteurs like Spike Jones, David Fincher, Sam Mendes, the Wachowskis, David O’ Russel, and Brad Bird were actively courted by the major studios and offered boatloads of cash to make scaled-up indie films. David Fincher even told Fox Studios that Fight Club could be a $3 million indie, but it would be so much cooler with $60 million.

Over time, this process would morph into the unfortunate form of “Oscar-bait” and lose its edge. Raftery points to 1999’s Cider House Rules as an early example.

1999 Was the Year of the Screenplay Writer

As seen in: The Matrix, American Beauty, Cruel Intentions, Dogma, Office Space, American Pie, The Sixth Sense, Stuart Little, She’s All That, Being John Malkovich

The writers for most modern big budget blockbusters today are typically in-house workmen who are very good at ticking the boxes for marketing, but aren’t auteurs in the cool, artsy sense. Even something like The Avengers isn’t just written by Joss Whedon, but rather goes through dozens of drafts commissioned by the studio. But because of the indie-mainstream hybrid boom in the late 90s, studios relied more on outside talent than ever. Random nobodies like M. Night Shyamalan, Charlie Kaufman, the Wachowskis, and Alan Ball were wandering into Hollywood studio meetings and getting multi-million-dollar sales for their screenplays.

Adam Herz couldn’t figure out what to call his movie, so he handed it to studio execs with the title: Untitled Teenage Sex Comedy That Can Be Made For Under $10 Million That Most Readers Will Probably Hate But I Think You Will Love. He sold the American Pie screenplay for $650,000.

Prequels, Sequels, and Remakes Had Yet to Take Over

As seen in: 1999 Box Office Records

I didn’t count, but according to Raftery, there were about 12 sequel and remake films in 1999, compared to 30+ for a normal year in the 2000s.

Granted, Star Wars: Episode I, Toy Story 2, Austin Powers 2, and The World is Not Enough were all big hits… but that’s pretty much it. I guess The Mummy and Wild Wild West are technically remakes, but their source material is so obscure they shouldn’t count.

Raftery attributes this trend both to audience desire for indie creativity, and to some high-profile sequel/remake commercial and critical failures from the last few years, including Batman Forever, Godzilla, and Lost in Space.

Nobody Could Predict Commercial or Critical Hits

As seen in: The Matrix, The Mummy, The Sixth Sense, The Blair Witch Project, American Beauty, Big Daddy, American Pie, She’s All That, Analyze This, Three Kings

Studio execs were consistently baffled by what did and didn’t make money. Most WB execs admitted that they literally didn’t understand what The Matrix was about, but despite being R-rated, it was the 5th highest grossing film of the year. The Mummy, despite having a sizeable budget, was assumed to be a bomb throughout production since it would have to compete in the same month with Star Wars, but it ended up being the 8th highest grossing of the year. M Night Shyamalan prayed that The Sixth Sense would recoup its $55 million budget so he would be allowed to make another movie, and then it ended up being the 2nd highest grossing movie of the year, only behind Star Wars. And The Blair Witch Project is still the most successful movie of all time on a budget-to-revenue basis.

Maybe the best indication of 1999’s film quality is that critics were so split on its best movies. Some people thought Fight Club was generation-defining, others thought it was juvenile edge-lord bullshit. Some people thought American Beauty was the most incisive look at American society in decades, while others thought (and many still think) the movie was a pretentious wank fest. Some thought Magnolia was one of the most beautifully ambitious films of all time, others thought it was a display of blatant auteur hubris (where do the frogs come from?). Some thought The Blair Witch Project was the scariest movie of all time, other people were literally vomiting in theaters.

According to Raftery, the only major films which received and sustained universal critical acclaim were Being John Malkovich and The Sixth Sense.

Audiences Loved Twist Endings, Time Lapsing, or Just Any Super Weird Narratives

As seen in: The Sixth Sense, Fight Club, Run Lola Run, Following, Being John Malkovich, Magnolia, Eyes Wide Shut, The Blair Witch Project, Go, Julien Donkey Boy, The Limey

1999 is full of movies which bend, break, or annihilate traditional narrative structures. Not only did critics appreciate the avant-garde streak, but studios figured out that audiences can really love this weird artsy stuff too.

Raftery attributes a lot of this trend to Pulp Fiction which redefined the narrative landscape in 1994. Suddenly lots of movies operated outside regular time flow, like Following (Christopher Nolan’s first movie), GoRun Lola Run, and The Limey. At the same time, Fight Club and The Sixth Sense had two of the best twist endings of all time. Meanwhile, insane people like Spike Jones and Paul Thomas Anderson were making indescribably bonkers movies like Being John Malkovich and Magnolia.

I guess the late 90s had some sort of happy confluence of creative filmmakers, excited audiences, and unusually risk-tolerant executives, which all came together to produce a slate of daring movies.

The Rise of the Internet

As seen in: The Blair Witch Project, Star Wars: Episode I, The Iron Giant, Wild Wild West, The Matrix

The internet was still being adopted by normies at the end of the 90s, but 1999 seems to be the precise year when it started to have a big impact on the film industry.

Star Wars: Episode I was the epicenter of the first truly internet-wide war as supporters and detractors of George Lucas argued whether the movie was complete garbage or merely mediocre. Studio execs blamed stupid nerds for tanking Wild Wild West after leaked special effects shots were shared before release. On the other hand, Brad Bird’s Iron Giant was almost single-handedly saved by online fans who built hype for the film as it languished in development hell.

But undoubtedly the most internet-impacted film of 1999 was The Blair Witch Project, whose marketers more-or-less invented online guerrilla marketing. They invented fake blair witch legends, put up fake websites, made fake documentaries, and even hung up MISSING posters of the cast members on college campuses. By the time the movie released, the studio estimated that 50% of The Blair Witch Project viewers thought the footage was real.

1999 Was The Last Teen Movie Boom

As seen in: American Pie, 10 Things I Hate About You, She’s All That, Cruel Intentions, Election, Varsity Blues, Never Been Kissed, O, Dick, Superstar

Not all trends are due to some deep shift in the zeitgeist; sometimes tastes just cycle. According to Raftery, teen movies had their peak in the 1980s with John Hughes, then completely crashed in the early 90s (try to think of an early-mid 90s teen movie), but then Dawson’s Creek and Buffy the Vampire Slayer led a revival in the late 90s. Studios found that teen movies were cheap and low-risk, so they went on a production spree.

1999 teen movies are notable for being edgy but earnest. 10 Things I hate About You has a strong neo-feminist backbone, Varsity Blues was a somber look at high school sports and student pressure, and American Pie greatly pushed the bounds of teen sex on film. Arguably Cruel Intentions was even more extreme, featuring suggestions of quasi-incest, and a straight-up lesbian make-out session. Election is a more nihilistic Fight Club/American Beauty-ish take on the interactions of teen and adult life, which IMO, is still super underrated.

However, the most financially successful of all these edgy, daring, genre-defining movies was She’s All That, which is easily the cheesiest among them (it originated the “a girl is ugly until she takes off her glasses” trope). Though, amusingly, it was heavily re-written by M. Night Shyamalan to get out of a shitty contract with the Weinsteins.

In retrospect, 1999 was probably the final crest of teen movie quality. After that point the only classic teen movies I can think of are Superbad, Mean Girls, and maybe Easy A, but all three are spread throughout the following 20 years. It seems like audiences got overwhelmed by the teen movie deluge, culminating in 2001’s underrated Not Another Teen Movie.

“Black Movies” Established a Niche outside “The Hood”

As seen in: The Best Man, The Woods

Raftery notes two small-mid budget films that were written, directed, and starred almost exclusively by black people, both of which quadrupled their production budgets at the box office.

In each instance, the production studios supposedly picked up the films to have a “black movie” on their roster, thereby making the studio look woke (in modern parlance). The executives all thought the movies would have trouble making money because black audiences don’t watch middle-classish movies, and white audiences don’t watch black movies, but The Best Man and The Woods ended up being sleeper hits any way. The former’s director, Malcolm Lee, says the same studio sentiment exists to this day, with his 2017 Girl’s Trip becoming an unexpected sleeper hit.

Romantic Comedies Were Still a Thing

As seen in: Runaway Bride, She’s All That, Never Been Kissed, Mickey Blue Eyes, Notting Hill, Forces of Nature, Message in a Bottle, The Bachelor, Blast from the Past, Three to Tango

Isn’t it weird how rom-coms sort of died? I mean, they still exist, but they seem mostly relegated to minor releases on Netflix and Amazon Prime now. I can’t remember the last rom-com box office hit; maybe those two “fuck buddy” movies? At best, quirky rom-coms like The Big Sick have a presence on the indie scene, but mainstream audiences don’t seem to care about rom-coms anymore.

There were no classic rom-coms in 1999 (maybe Notting Hill is the closest?), but the genre was still alive and well. In one of the biggest box office years ever up until that point, there were plenty of straight-forward decently successful rom-coms, the top of which was Runaway Bride, the 10th highest grossing movie of the year.

I’m not a rom-com fan so I don’t consider the decline of the genre to be a tragedy. But for what it’s worth, 1999’s Blast from the Past is probably my second favorite rom-com ever (behind Punch Drunk Love). It’s another super underrated movie, and is maybe the only non-religious, pro-cultural conservative movie I can think of.


As seen in: Eyes Wide Shut, Magnolia, almost every other movie in 1999

Every single film production meeting in 1999 had a moment where some executive suggested getting Tom Cruise in the movie. It didn’t matter how big or small the movie was: execs floated getting Tom Cruise to play “Neo” in The Matrix and “Laurence” in Office Space. New Line was so desperate to keep Paul Thomas Anderson around after Boogie Nights that they gave him carte blanche for Magnolia, which included buying him Tom Cruise.

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Cultural Trends

Everyone Hated Comfortable Middle-Class Existence

As seen in: Fight Club, The Matrix, American Beauty, Office Space, Being John Malkovich, Election, Cruel Intentions, SLC Punk

There were a lot of excellent comments on this here, but I’ll try to encapsulate.

Based on a lot of 1999’s best movies, there was a sense that the American life was hollow. People imagined this template of a large suburban house, a white picket fence, pristine interior design, a steady well-paid office job, a decently attractive wife, and 1-2 moody kids, as the apex of civilization. This was the thing that we, all of humanity, had been working towards throughout all of history. It was the ultimate prize that the masses could ever hope to achieve – safety, security, wealth, comfort, and companionship. By the late 90s, this vision was in our grasp. The Cold War was over, the stock market was booming, everyone was getting their own computers, and so it seemed like humanity had achieved its apex of existence.

And apparently it sucked.

Many of 1999’s best movies are about people “trapped” in this lifestyle. The best part of Lester Burnham’s day is jerking off in the shower. Peter Gibbons considers every day of work to be the worst day of his life. The narrator loathes himself for being excited to flip through an Ikea catalogue. Jim McAllister envies his disgraced coworker because he got to have sex with one of his high school students. Thomas Anderson is so bored and detached that reality itself feels metaphysically unreal.

These are the realities of the supposedly perfect middle-class white-collar suburban family-oriented existence. It’s a whole bunch of people (usually men) feeling bored, unsatisfied, and especially meaningless. They all did what they were supposed to (went to college, got a job, got married, got a house, etc.) and basically completed life. And they found nothing at its end. No excitement, no deep value, no meaning, just going through the same motions as everyone else in a well-worn mold.

That’s what these movies are about. They’re about the deep existential misery of doing everything right but being unfulfilled. They’re about realizing that the things that are supposed to bring you happiness can become straight-jackets.

I think all the listed movies focus on a different aspect of this core theme. Fight Club focuses on the loss of masculinity, Office Space on corporate work culture, American Beauty on the family, Being John Malkovich on the suppression of passion, The Matrix on existentialism, Election on sexual unfulfillment, etc. Some great comments from the previously linked thread really nailed it:


Interestingly three big movies came out in 1999 about the weird feeling of wrongness one gets from a routine of getting up, going to work and building a comfortable and safe middle class life. All three present some kind of fantasy of how one might escape.

For the artsy hollywood types there was American Beauty. This was about the fantasy of saying fuck it, giving up your boring office career, smoking pot and realising that you could have fucked the hot cheerleader all along (but don’t since you’re too moral for that)…

For the edge lord intellectuals we have Fight Club…

Finally, for everyone else there was The Matrix. The Matrix got to the point the most effectively (my opinion on this was largely cribbed from this podcast). Morpheus explicitly tells Neo during the pill scene, yeah you can wake up and see what a prison society is and drop out, really understand how artificial and fake all your achievements are. It means though that you give up everything. Every creature comfort and safety net and all of the stability you get from this system. That’s the trade you make to be come and reclaim your masculinity.


But at the same time [Office Space] tapped into the culture’s spite for office jobs and encapsulated the misery that is submitting to a meaningless 9 to 5 job under a boss that you hate with co-workers you mostly don’t get along with all while knowing full well that you’re a replaceable cog. And of course the wish-fulfillment fantasy of saying “screw this” and just checking out to go do what you want and then really sticking it to the man by getting rich by scamming them for a couple hundred thousand dollars.

So it resonated.


I too noticed the pattern of movies that venus notes in this thread. They all had an impact, that was a big year for me. But by far, my favorite was Fight Club.

Two years after that film dropped, I dropped out of college, joined the Army, and found that there really is gold at the end of that rainbow. There really is fulfillment and purpose and bonds that strain the definitions of “friendship”. All you have to give up is everything you thought you liked and needed. It’s not the military specifically, which is mostly a fetid bureaucracy of such scale of incompetence it beggars belief. But it is the vehicle that will put a man in combat, and that will bind him to the other men with him, and should he see combat and meet the challenge, it will change him forever. Everything a man does in life, sport and work and civic engagement is all just a tiny, pale substitute for what he’s supposed to be doing. Combat has a way of sandblasting one’s character down to the sliver of essential-ness. You find out who you really are, what you really need, and who will give it to you.

There has been a lot of backlash against these movies and themes in recent years, with modern critics considering the “heroes” of these movies to be privileged, entitled, and winy, but I think that perspective completely lacks empathy. To me, these movies present the ultra-empowering message that you control your own life. No matter who you are, what you’re doing, or what inertia you’re trapped in, you always have the ability to steer your life to where you want it to be. Granted, there are plenty of terrible ways to steer your life (I do not condone joining fight clubs or blackmailing your corporate boss) but there are always better paths available. You just need the willpower to find them.

Everyone Thought Marriage Sucked

As seen in: American Beauty, Being John Malkovich, Double Jeopardy, Story of Us, Fight Club, Election, Eyes Wide Shut, Magnolia, The Insider, Varsity Blues

I didn’t dig into the statistics, but Raftery notes that American divorce rates spiked in the 1980s, during a cultural shift towards empowering women and the aftermath of the sexual revolution. The filmmakers of the late 90s were the children of these divorced parents. So it’s no surprise that so many 1999 movies were about unsteady or crumbling marriages.

To me, 1999 feels like a flare-up of the long-winding post-1950s cultural attitude towards marriage. The 1950s placed the strength of a traditional marriage and family life at the heart of society, as displayed in tv shows like Leave it To Beaver, Father Knows Best, and I Love Lucy. Even into the 90s, this was still the mainstream portrayal of families with shows like The Cosby Show, Home Improvement, and The Fresh Prince of Bel-Air. But then came along subversive shows like The Simpsons and Married with Children which pushed back on the idyllic family images. They portrayed fathers as plodding, clueless, and clearly not satisfied with their lot in life, while wives tended to be bored and frustrated. It may seem quaint and broad today, but Married with Children’s Al Bundy was something of a proto-Lester Burnham.

More proximately, the biggest scandal of 1999 was President Bill Clinton cheating on his wife with a young intern. The most clean-cut, refined, presentable husband and wife in America were having marital problems for all to see.

By 1999, it seems like the idolization of the family had broken down in popular culture and a Simpsonized portrayal had taken hold. The big movies of the year further explored this territory by looking at marriages that started as the ideal but had eroded under the realities of life.

Tom Cruise and Nicole Kidman are two of the hottest people on earth, but they’re a sexually frustrated couple in Eyes Wide Shut. Lester and his wife in American Beauty appear perfect to their neighbors, but have a sexless, hollow marriage which leads the husband to constantly fantasize about his teenage daughter’s friend, and the wife to cheat with her business competitor. The protagonist couple in Being John Malkovich both fall in love with the husband’s co-worker, and they end up body-jumping in their attempts to seduce her. Even the unmarried narrator of Fight Club laments his father for leaving his mother to start new families in multiple cities like he’s “setting up franchises.”

A particularly interesting case is The Insider. Michael Mann’s movie is based on the true story of a big tobacco executive who becomes a whistleblower against his industry. Arguably the main antagonist in the movie is the exec’s wife, who urges her husband to not speak out against his employer out of fear that he will lose his affluent lifestyle. In a story packed with corporate intrigue, media analysis, fights between old and new culture, etc., Mann decided to focus much of the narrative on the protagonist’s marriage.

Everyone Was Intrigued by What Future Technology Would Do to Society

As seen in: The Matrix, eXistenZe, The Thirteenth Floor, Deep Blue Sea, EDtv, Bicentennial Man, Virus, Being John Malkovich

There’s a good case to be made that the late 90s were the biggest leap forward in mass-consumer technology ever. Between the rise of personal computing and the internet, everyone had this infinitely large, complex world unfurl before them, and apparently a lot of people had no idea what would happen. A lot of 1999’s sci fi movies are explorations of the technological possibilities of these trends, with varying degrees of predictive accuracy.

The Matrix is about all of humanity being enslaved by rouge AIs who keep their human batteries happy by locking them in a computer-simulated dream world. In eXistenZe, a VR world is so realistic that pro-reality extremists try to destroy it. Both movies, along with The Thirteenth Floor and Being John Malkovich speculate on how the concept of “identity” might break down as we transition more of our lives from a static real world to an infinitely fluid digital one.

It’s notable that most of these movies were fairly optimistic about technology. Even though The Matrix shows a worst-case-scenario, it also displays technology as a source of personal empowerment to make yourself who you want to be, and as a means of finding genuine, like-minded communities. Both ideas undoubtedly resonated with the directors of The Matrix, a pair of (future) trans women.

People Wondered If They Were in the Pre-Apocalypse

As seen in: Fight Club, Magnolia, End of Days, The Matrix, Blast From the Past

While people were broadly optimistic about technology, there were a decent number of movies which included the apocalypse, or something like it. This was undoubtedly related to fears over Y2K, whether of the hokey religious/new age variety, or the apparently legitimate computer bug sort.

The 2000s have been dominated by post-apocalypse films/video games/tv shows, like Hunger Games, Walking Dead, Fallout, Mad Max, etc. But 1999 was focused more on the pre-apocalypse. Fight Club showed the downtrodden forces which fight back against a decadent society by blowing up credit card companies and wiping the debt record clean. Though The Matrix actually took place in the post-apocalypse, its focus was on the computer-generated simulation of the pre-apocalypse and the complacency which led to its downfall. More abstractly, Magnolia concludes with a shower of frogs falling from the sky for no reason which inexorably alters the lives of its many characters.

Americans Loved and Feared Violence

As seen in: The Matrix, Fight Club, American Beauty, O, 8MM

Raftery mixes brief forays into news stories between his movie summaries to provide some current affairs context to what cinema-goers were thinking about. By far the most impactful news story of the year was the Columbine High School massacre.

In the aftermath of the school shooting, the biggest question on everyone’s mind was “why?” Naturally, a lot of pundits turned to youth culture for an explanation. Suddenly the 90s were being recast as a decade of extreme violence and moral degeneration. Kids spent all their time listening to weirdo Marilyn Manson and watching ultra-violent Pulp Fiction. The US Congress even launched a series of formal investigations into the causal link between violent movies and youth crime. Columbine would hang heavily over the rest of the year and impact how films were made by studios and received by audiences and critics.

While it’s easy to look back and mock the moral panic, the unprecedented horror of Columbine caused understandable distress, especially when a film-influence on the killers was at least plausible. The black leather trench coats worn by the killers were reminiscent of The Matrix (which was in theaters at the time), and Heathers and Basketball Diaries were two recent high-profile movies which featured school shootings.

Though Congress never ended up passing any violent movie laws, spooked movie studios took the investigations as a message to get their houses in order. A lot of movies featuring youth violence were cancelled. O, a completed teen movie based on Shakespeare’s Othello, was shelved and not released until 2001.

Critically, many violent releases in 1999 (especially those featuring teens) received colder receptions than they otherwise would have. Fight Club was especially hit hard by accusations of promoting exactly the sort of nihilism that the Columbine killers embraced. The film may even have gotten a delayed release in anticipation of the controversy.

Americans Were Still Figuring Out Sexual Liberation

As seen in: Cruel Intentions, Election, American Pie, American Beauty, The Virgin Suicides, Eyes Wide Shut, Boys Don’t Cry, Deuce Bigalow: Male Gigolo, Never Been Kissed

1999 was a big year for putting taboo sexuality on screen.

Cruel Intentions had a much-publicized lesbian make out featuring the most beloved teen actress on earth (Sarah Michelle Geller), and suggested quasi-incest. American Beauty and Election featured older men fantasizing and having sex with young female students. American Pie was packed with unprecedented horny teen debauchery and, of course, fucking a pie. Eyes Wide Shut had two of the most recognizable actors in the world going to orgies and talking about open marriages. Boys Don’t Cry was about a trans man pretending to be a cis man to seduce a woman, and had hardcore-enough sex scenes to receive an NC-17 rating on its first cut.

(Even Deuce Bigalow: Male Gigolo is kind of edgy with its male prostitution, amputee female love interest, and take on what drives female sexual frustration.)

I was seven-years-old in 1999 so I don’t have much of a sense of what the sexual cultural mores were at the time. But the year’s films seemed like an attempt to push them further.

There Was Something Weird Going on With Religion

As seen in: Dogma, End of Days, Stigmata, The Matrix

I’m not sure what to say about this except that 1999 had quite a few weird movies which used Christian imagery, themes, and theology for horror, action, and fantasy stories. Maybe these movies were early examples of subversion of mainstream religious views; possibly precursors to the “religion vs. atheism” internet wars of the early 2000s.

LGTBQ+ Wasn’t Mainstream, but It Was Right Beneath the Surface

As seen in: American Beauty, The Talented Mr. Ripley, Fight Club, Girl Interrupted, Magnolia, Cruel Intentions, Being John Malkovich, The Matrix, Blast from the Past, Boys Don’t Cry

I thought this was one of the most interesting trends I found in the 1999 movies. With one exception, there were no notable 1999 movies directly about queer identities, but there were tons of movies with queer subtext or themes on the margins.

The Talented Mr. Ripley, Fight Club, and Girl Interrupted are all quite homoerotic with their highly intimate same sex friendships at the centers of the narrative. American Beauty and Magnolia both have closeted gay characters who are simultaneously terrified of being outed but crave recognition for their true selves. Cameron Diaz’s character in Being John Malkovich unexpected falls in love with another woman, and after test driving Malkovich’s body, briefly declares herself to be a trans man. And while it was mostly played for salaciousness, Cruel Intentions broke boundaries with its hot lesbian kiss, especially since both characters were straight (ish).

The big exception to the rule was Boys Don’t Cry, which was genuinely ahead of its time with the true story of a trans man who was raped and murdered in Texas after his trans status was revealed. Prior to Boys Don’t Cry, trans people tended to be portrayed in films as crazy/manipulative villains, like in Silence of the Lambs, Crying Game, and Ace Ventura: Pet Detective.

The other interesting case was The Matrix, which upon release didn’t seem to have a queer element besides one minor character who is implied to be trans (Switch). But with both Wachowskis coming out as trans women years after the film’s release, it’s easy to read The Matrix as a trans narrative.

Through 1999’s filmscape, I think I can see that queer issues were bubbling right beneath the surface in American society. Don’t Ask, Don’t Tell was passed in 1993, and gay marriage legalization was still a fairly marginal view, especially outside of deep blue territory. So while queerness wasn’t brought to the artistic forefront in the way it is now (by my count, 4/10 Best Picture nominees in 2018 have prominent queer characters/themes, 3/10 for 2017), queerness was just starting to go mainstream in 1999.

3 thoughts on “Examining 1999’s Culture Through Its Best Movies

  1. It seems like you are assuming there’s an unlimited number of good indie scripts being written each and every year and that the only thing that matters is whether or not the ‘executives’ are willing to take a risk and dip into them. An alternative hypothesis is that 1999 was just a year in which an unusually large number of good indie scripts were written and that they got greenlighted due to their unusually high quality rather than because executives were more susceptible to them than ever before. This is based on my prior that the fiction being produced in any given year represents the best that the sum of screenwriters and regular writers can come up with for that year, that fiction is hard and the bottleneck is in creating it in the first place rather than getting boogeyman executives to throw money at it.


  2. Fantastic analysis. One note – I believe

    “Prequels, Sequels, and Remakes Had Yet to Take Over

    As seen in: 1999 Box Office Records”

    is supposed to be section header text – its currently just paragraph text


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