*Last month, I looked back at my favorite films turning 30 this year, so I figured that this month should feature my 10 favorites turning 25.

1999 felt like a turning point not only for me, but for the country at-large. We had Y2K hysteria, the embarrassment of a presidential impeachment trial, the corporate nihilism of Woodstock ’99, the anti-globalization protests in Seattle, and confusion as to why two teenagers would turn to violence at Columbine High School. While the Internet was there through all of it, the idea that we could exist offline still felt like a realistic possibility.

The turmoil in America mirrored the turmoil that was occurring within me as I prepared to enter junior high school. My frustration with being an introvert had reached its peak and I knew that my road to assimilation wasn’t going to be easily navigated given how the entire system was built around The Extrovert Ideal.

A lot of things were happening, but the movies were always there. Sure, there were serious films being made; however, those that put butts in the seats weren’t trying to remind you of how awful the outside world was. Escapism was allowed and entertaining as opposed to virtue signaling was the ultimate goal.

Even films that didn’t make my list such as “The Mummy,” “Austin Powers: The Spy Who Shagged Me,” “Big Daddy,” “Galaxy Quest,” and “Mystery Men” were tons of fun, so the depth of what Hollywood was putting out away from the awards picture puts the present day to shame.

What follows is a list of my 10 favorites from ’99 as well as five honorable mentions that are worthy of your time.

“Being John Malkovich” – Directed by Spike Jonze

One of my favorite films of any year, because it’s unlike anything else that’s ever been written. John Cusack, Catherine Keener, and Cameron Diaz have never been better, especially with Diaz showing a glimpse of what her career could have been had she pursued more eclectic material. Going in with as little knowledge of the plot as possible is ideal for maximum return.

“Fight Club” – Directed by David Fincher

Fincher turns Chuck Palahniuk’s already lacerating source material up to 11 and creates one of the decade’s defining cinematic statements.

“The Blair Witch Project” – Directed by Daniel Myrick and Eduardo Sanchez

An acquired taste for some, but I can’t speak highly enough of what they were able to accomplish with this film from both a storytelling and marketing standpoint. So simple yet so effective.

“The Insider” – Directed by Michael Mann

1995’s “Heat” is probably Mann’s masterpiece, but this one is pretty darn close.

“Bringing Out the Dead” – Directed by Martin Scorsese

Nicolas Cage’s body language tells the story here and he has previously referred to it as one of the best films he’s ever taken part in.

“Magnolia” – Directed by Paul Thomas Anderson

Anderson follows up “Boogie Nights” with another ensemble-driven masterpiece.

“Boys Don’t Cry” – Directed by Kimberly Peirce

Easily the most uncomfortable watch on this list, but the results speak for themselves.

“Summer of Sam” – Directed by Spike Lee

Not one of Lee’s most overanalyzed films, but definitely one that deserves deeper consideration.

“The Sixth Sense” – Directed by M. Night Shyamalan

Shyamalan has become a joke to many in the ensuing decades, but his first foray into the Hollywood machine is a reminder of how good he can be.

“Eyes Wide Shut” – Directed by Stanley Kubrick

Its reputation preceded its release, but Kubrick confronts a lot of uncomfortable truths about America’s ruling class that people weren’t quite ready for back then.

Honorable Mentions: “Arlington Road,” “Toy Story 2,” “The Matrix,” “The Virgin Suicides,” and “Sleepy Hollow”

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