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The piano riff every kid who took lessons tried to learn. Vanessa Carlton's "A Thousand Miles" owned 2002 radio, then got a whole second life in White Chicks, with Terry Crews belting every word in absolute earnest. It belongs equally to burned CDs, karaoke nights, and the meme age that followed.
The Canadian teen-pop star who reinvented herself as the voice of 90s female rage. Raw, oversharing, absolutely unapologetic about her feelings—she gave the decade permission to be a mess and call it art.
Duncan Sheik's brooding acoustic single became one of the defining adult-alternative hits of 1997 — and one of the longest-charting songs in Billboard history, quietly clinging to the Hot 100 for more than a year.
Folk's answer to the underdog dream: Jewel went from a coal-heated Alaska homestead to living in a van in San Diego to 12× platinum. Her breakthrough Pieces of You rode a slow burn to the top, and by the late 90s she was unavoidable — poetry collections, platinum albums, two generation-defining radio ballads that felt permanent.
![Video thumbnail — Michelle Branch - Everywhere [Official Music Video]](https://i.ytimg.com/vi/HLCasyAh7ic/maxresdefault.jpg)
A teenager who wrote her own songs and played her own guitar in a sea of choreographed teen-pop — Michelle Branch's "Everywhere" was the anti-TRL anthem that somehow became peak TRL. That driving guitar, the spy-on-the-cute-neighbor video, and the fact that she wrote it herself made her the authentic alternative of fall 2001.
Four chords, a campfire strum, and a chorus anyone could sing on the first listen — Eagle-Eye Cherry's "Save Tonight" was the acoustic one-hit wonder of 1998, an easygoing plea to make the most of a last night together.
Pretty, gentle, and secretly about a woman burning her house to the ground — Shawn Colvin's "Sunny Came Home" swept the 1998 Grammys, winning both Record of the Year and Song of the Year.