In 1999, I was a sophomore in high school, I got my drivers’ license, and I gave my life over to Christ and decided to go into full-time ministry. Clearly, it was a big year for me, but what about in Hollywood?

On a recent episode of the Filmspotting podcast, longtime hosts Josh Larsen and Adam Kempenaar listed their top 5 years of film. This is one that was on both of their lists. So it shouldn’t surprise you that in this highly favored year that I am going to have more than 1 number 1. Unlike 2007, this one isn’t so much a tie as it is the consideration of this exercise as a death match. If only the winners from each year are left for eternity to represent that year, then I need both of these films because they speak to the larger shift in cinema.

In my mind, the films of a year speak to the cultural landscape of the time, and prior to 9/11 in 2001, one of the biggest cultural shifts (at least in my life) was the school shooting at Columbine school in Littleton, Colorado on April 20, 1999. Today, it seems like school shootings happen everyday and they don’t have time to linger on our consciousness the way they did because of the constant barrage of the news cycle. At the time, I don’t think that Columbine played a role in that decision, but it definitely shaped my life from that point forward.

The films of 1999, whether I saw them at that time or years later, have solidified my love and passion for cinema. I was a film lover years before I became a Christian, but my entire worldview shifted in a moment and these films form a cultural microcosm for me and speak deeply.

Back in 1999, almost 20 years ago, Jeff Gordiner wrote for Entertainment Weekly and spoke with great insight about this cinematic shift. He gave some evidence:

The whirling cyberdelic Xanadu of The Matrix. The relentless, rapid-fire overload of Fight Club. The muddy hyperrealism of The Blair Witch Project. The freak show of Being John Malkovich. The way time itself gets fractured and tossed around in The Limey and Go and Run Lola Run. The spooky necro-poetry of American Beauty and The Sixth Sense. The bratty iconoclasm of Dogma. The San Fernando Valley sprawl of this winter’s Magnolia. Were you prone to theatrical pronouncements, you might say that not since the annus mirabilis of The Wizard of Oz, Gone With the Wind, and Stagecoach has Hollywood brought so many narrative innovations screaming into the mainstream. ”It’s like 1939,” marvels director Alexander Payne, whose dark satire Election represents yet another escape from the fuddy-duddy format. ”There’s a bumper crop of movies that, even if they’re not perfect, are interesting and intelligent.”

I could fill an entire post with just notes on these honorable mentions and 1999 events, but instead I will give you a funny story and then get on with my top films.

In the summer of ’99, I was on vacation with my parents and while camping, the heat was unbearable. We decided to get out of the heat by entering my favorite place on earth. My parents had heard interesting things about this risque final film from Stanley Kubrick who had died earlier in the year just after production wrapped. If you don’t know, that film is Eyes Wide Shut, an erotic drama that follows the sexually charged adventures of a man, Tom Cruise, who embarks on a night-long adventure, during which he infiltrates a massive masked orgy of an unnamed secret society. I had also heard some things about that film and I decided that I did not want to watch it as a 16-year-old boy sitting next to my mom and dad!

I asked if I could bypass it and see the only other film playing at this little country theater: Muppets from Space. Finally escaping the heat, I allowed the air conditioning to overcome me and I took a nap in the theater as the movie droned on. That is the only time I can ever recall falling asleep in a movie theater. After the films were over, we got in the car and my parents never mentioned the film again.

Honorable Mentions

I could make an argument for any of these honorable mentions to be in the top three of the year if not on the absolute top of the heap.

• They include what could easily be considered Paul Thomas Anderson’s best film in Magnolia.
• The return of passionate animation with real emotion and great talent with Brad Bird’s Iron Giant and the amazing Toy Story 2, which was a pleasant surprise because it could have ended up as a direct to VHS feature like so many of Disney’s garbage sequels did.
• American Beauty rushed into Oscar consideration with its bold messages about suburbia and the dark secrets lying behind closed doors, it resonated with voters reeling from a massacre of students at the hands of other students in what should be one of the safest laces on earth.
• In The Green Mile we got a beautiful retelling of a Stephen King novel series by director Steven Spielberg that dealt with pain and loss as well as understanding someone different from yourself.
• We entered the enigmatic and fantastical world of Spike Jonze in Being John Malkovich and then we’re dumped off the side of the highway outside town.
• This was back when we had a director named M. Night Shamalayan that we knew nothing about, and he gave us his best film to date, The Sixth Sense.
• The horror genre changed overnight with a little idea called found footage and we were introduced to The Blair Witch Project.
• Office Space spoke to the angst and fury of those locked in the office building in much the same way that Fight Club speaks to the same of those in Service industries.
• In Man On The Moon, We learned how quirky and interesting Andy Kaufman was, how much we change to fit others expectations of us, and how deeply method Jim Carrey can be when he’s sinking in that.
• David O’Russell gave us a powerful look at the Gulf War and it speaks even louder today in Three Kings.
• All the way back in 1999 Hilary Swank was tackling the idea of transgendered rights in Boys Don’t Cry.
• Then there is still Girl, Interrupted, The Boondock Saints, Talented Mr. Ripley, 10 Things I Hate About You, Galaxy Quest, and so many more.

Fight Club

David Fincher captured the emotions and ideas of a generation and put it into action. This film did not do well when it was released partly because of how close it was to the cultural event that we’ve already looked at. The wound was too fresh and many saw in this film all of the violence and nihilism present in the perpetrators of that violent act.

Dennis Lim writing for The New York Times reflected on this at the film’s 10 year anniversary:

The nervousness over screen violence was at a renewed high in the wake of the shootings at Columbine High School, and this must have seemed like the worst possible time to release a film in which an army of alienated men, led by Brad Pitt’s charismatic Tyler Durden, an übermensch in a red leather jacket, engage in bare-knuckle brawls, antisocial vandalism and outright revolutionary terrorism. When “Fight Club” opened in October 1999 after much defensive maneuvering from the studio (which delayed the release and struggled to find a marketing hook), the pundits eagerly took aim.

I’m not going to break the first rule of Fight Club here, but I will just say that it is a film that I would not leave behind. It must go on and represent this end of a millennium movement.

The Matrix

What a strange premise for a movie. Equally the story of a man silently moving about his boring life all the while actually being part of a sinister computer program that was using his biochemistry as a battery and the remnant of fighters who were resisting this control and fighting back. It is an addictive adrenaline rush and the fervor fed an animated version and two sequels.

Keanu Reeves was so good that he is still essentially playing the same character as John Wick. The Wachowski brothers did something spectacular with this film and its overall message resonated like Fight Club with disaffected and depressed adults and teenagers living at the turn of the millennium facing Y2K and the threat of a computer takeover. It is endlessly rewatchable and the effects still hold up 20 years later.

So, what do you think? Did I get this one wrong? What is your best movie of 1999? Speak up and let me know. Next we’ll be looking at 1998, you can send me your thoughts by commenting here or on social media. I’m @engagingculture on Twitter and our Facebook page is Life At The Movies.