4 Iconic Songs from Movies Released 25 Years Ago

Under the glitching shadow of Y2K, 1999 was a great year for movies.

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Twenty-five years ago, Hollywood produced Fight Club, The Blair Witch Project, Star Wars: Episode I—The Phantom Menace, The Matrix, American Beauty (and Pie), Runaway Bride, The Sixth Sense, Summer of Sam, Being John Malkovich, and Eyes Wide Shut, among others.

In 2019, culture critic Brian Raftery published a book called Best. Movie. Year. Ever.: How 1999 Blew Up the Big Screen. Is it hyperbole? The 1999 movies not mentioned above—Boys Don’t Cry, The Best Man, Office Space, Magnolia, Election, and Three Kings—offer additional support to Raftery’s view. He writes that these films changed filmmaking and gave audiences a “first glimpse of the coming 21st century.”

Regardless of whether 1999 (or 1979 or 1939) is the best movie year ever, the film songs below are a nostalgic mix of timeless classics and Gen X time stamps. So, in case you forgot how great cinema was back then, here are four iconic songs from 1999 movies.

“Yeah, Baby! Yeah!”

“Ready to Run” by The Chicks

“Ready to Run” appeared on The Chicks’ fifth studio album Fly and the soundtrack to the Julia Roberts and Richard Gere rom-com Runaway Bride. A fiddle and penny whistle begin The Chicks’ single with a freeing Celtic groove. Natalie Maines sings she’s not ready to be anyone’s bride. Instead, she’s running in the opposite direction. What’s all this talk about love?

“Yoo Hoo” by Imperial Teen

Imperial Teen’s indie pop jam “Yoo Hoo” drives the iconic scene from Jawbreaker where the girls stroll with impossible coolness through the halls of Reagan High School. Before they enter, Courtney Shayne (Rose McGowan) delivers a pep talk to her friends while Liz Purr (Charlotte Ayanna) is dead in the trunk of the car: “But you are gonna walk into that school and strut your s–t down the hallway like everything is peachy f—ing keen. Get it?” Got it.

“Beautiful Stranger” by Madonna

Following Madonna’s brilliant and best (Was that said out loud?) album Ray of Light, she and producer William Orbit wrote “Beautiful Stranger” for Austin Powers: The Spy Who Shagged Me. In the swirling music video, Austin Powers (Mike Myers) is seduced by Madge. Though Powers drives a Shaguar, he’s no match for the Material Girl. It’s an electronic and psych-pop banger and you’re officially dared not to sing: Da-da-da-da-da-da, da-da-da-da, dum.

“Playground Love” by Air feat. Gordon Tracks

Sofia Coppola’s unique instinct for music has shaped her films in ways that make her soundtracks must-own souvenirs. The French electronic duo Air scored her debut film The Virgin Suicides and “Playground Love” remains one of Air’s defining compositions. The song features vocals by Gordon Tracks, who is better known as Thomas Mars, lead singer of Phoenix. He eventually married Coppola in 2011. Air’s dark score captures the unavoidable tragedy of the Lisbon girls. If Air had released The Virgin Suicides as a standalone album, it would stand tall alongside their masterpiece Moon Safari. Unparalleled, Coppola has set the benchmark for indispensable soundtracks.

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