2. Aimee Mann: “Save Me”
The songs of the former ’Til Tuesday frontwoman Aimee Mann recur throughout Paul Thomas Anderson’s 1999 epic “Magnolia,” as if Mann is a kind of benevolent musical narrator looking down from above and threading together the plot’s populous sprawl. This cleverly off-kilter ballad was nominated for the Oscar for best original song but lost to Phil Collins’s schmaltzy “Tarzan” theme “You’ll Be in My Heart” — an injustice, if you ask me.
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3. Madonna: “Beautiful Stranger”
A good tweet I saw a few weeks ago, on Madonna’s birthday: “Happy birthday Madonna and thank you for putting the greatest song ever inexplicably on the Austin Powers: The Spy Who Shagged Me soundtrack.” Only slight hyperbole! Here, Madge and her “Ray of Light” collaborator William Orbit elevate what could have been a throwaway soundtrack trifle into a groovy bop that earns its placement on her greatest hits collection.
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4. Air featuring Gordon Tracks: “Playground Love”
Music plays a crucial role in Sofia Coppola’s cinematic worldview — so much so that I’ve already compiled an Amplifier playlist of her best needle drops. That musical sensibility was already apparent in her 1999 debut film, “The Virgin Suicides,” which features a dreamy, ethereal score by the French duo Air. The vocals of this theme come from a mysterious singer credited as Gordon Tracks, which is actually an alter ego of the Phoenix frontman Thomas Mars, Coppola’s future husband.
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5. Suga Bang Bang: “Don’t Test/Wu Stallion”
In his score for Jim Jarmusch’s unconventional hit-man flick “Ghost Dog: The Way of the Samurai,” the Wu-Tang Clan’s RZA perfectly captures the movie’s haunting, elliptical feel. Anchored by a breathy vocal loop, this hypnotic track by the Wu-Tang-affiliated reggae artist Suga Bang Bang envelops Forest Whitaker’s titular character in a mysterious haze.
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6. Imperial Teen: “Yoo Hoo”
Though not much of a hit when it was released in February 1999, the caustic teen comedy “Jawbreaker” has since become a cult classic, perhaps even inspiring certain elements of “Mean Girls.” This eerie but infectious tune by the alt-rock band Imperial Teen soundtracks an indelible moment when the main characters do a dramatic walk down their high school hallway — and a subsequent parody scene in the 2001 spoof “Not Another Teen Movie.”
▶ Listen on Spotify, Apple Music or YouTube
7. The Chicks: “Ready to Run”
The spunky lead single from the Chicks’ 1999 album “Fly” was a natural fit for the rom-com “Runaway Bride,” which reunited “Pretty Woman” co-stars Julia Roberts and Richard Gere with the director Garry Marshall.
Read More: 10 Unforgettable Songs From 1999 Movies
