This summer, I dragged my mom to The Clairidge—a single screen movie theater in Montclair, New Jersey—for a matinee of Alexander Payne’s “Election.” The theater was featuring a series, titled “Clash of the Claridge Classics: 1939 vs 1999,” in which the audience could watch two films from the respective years and vote for their favorite.
“Election” was always a special film to me. During my senior year of high school, I did a parody of it for my mass media class. I played a spoof on Tracy Flick, Reese Witherspoon’s character, who in the film was frenzied and dying to be elected class president. I directed, edited and starred in this project. An endeavor that led high=school me to want to become the next Sofia Coppola (one can dream).
Seeing it on the big screen made me extremely jealous of those who were able to experience its greatness in 1999. When asking my friends about their favorite films, coincidentally enough they were all released in that same year. 25 years later, here are films that continue to impact audiences.
“10 Things I Hate About You”
The first time I watched this film, I wanted to be just like Kat Stratford. She was angry, unapologetically feminist and reading a comically large copy of Sylvia Plath’s “The Bell Jar.” In a sea of one note female rom-com characters, I found solace in “10 Things I Hate About You.”
25 years later, it holds up. Loosely based on Shakespeare’s “The Taming of the Shrew,” the film follows two sisters, Kat and Bianca. as they navigate their father’s dating rules. Bianca wants to date but is only allowed to if Kat does (spoiler alert, she wants nothing to do with relationships). This movie is filled with stellar performances from early stars like Joseph Gordon0Levitt and Heath Ledger and it has the most fun ‘90s soundtrack filled with songs from The Cardigans and Letters to Cleo. It is the ultimate sleepover movie and the easiest to rewatch.
“But I’m a Cheerleader”
Director Jamie Babbit wanted to make a “gay Clueless” with her 1999 film. At its core, “But I’m a Cheerleader” is a colorful satire working against homophobia. The story follows Megan, a high school cheerleader sent to a conversion camp. Although it sounds dark, it is sheer campy bliss. RuPaul even shows up to lead Megan’s intervention, stating, “I myself was once a gay, now I’m an ex-gay, Megan.” It is a timeless tale of girl meets girl and continues to empower young queer people. Not to spoil it, but it is rare to find a LGBTQ+ story with a happy ending, making this a must watch all these years later.
“Fight Club”
Odds are if you ask a man his favorite movie it will most likely be “Fight Club.” This movie truly has everything. Toxic masculinity, consumerism and Brad Pitt. Director David Fincher went all in for this one, creating an immersive experience for each viewer. The film follows an insomniac who meets a soap salesman, and the two decide to start a fight club to get out their pent-up aggression. The club catches on, leading to an out-of-control trend. With an electronic score, it’s hard not to get excited while watching. It is a classic for a reason and a staple top 4 pick for Letterboxd users. Don’t let yourself get discouraged by the film bros as this is a fantastic watch.
“The Virgin Suicides”
There is nothing like a hazy Sofia Coppola film. “The Virgin Suicides” follows the lives of the Lisbon sisters through the eyes of neighborhood boys. On the outside, the Lisbons seemingly live a normal suburban lifestyle, but their reality is much darker. Coppola’s work is masterful as it captures the allure and mystery of the sisters through soft lighting and dreamy atmospheres, whilst also hinting at the melancholy nature of their lives. The boys’ gaze is almost a character in the film as it transforms the Lisbon sisters into a distant memory rather than fleshed out people.
At its core, this film is an easily romanticized tragedy, but a visually stunning commentary on mental health.
Although these are some of my favorites, there are countless other films from 1999 to check out. 25 years later, these films remain timeless and continue to invite new generations to take a peek.
