Avril Lavigne
The Canadian pop-punk singer who defined early-2000s teen rebellion with a necktie knotted over a tank top, chain wallets, and an I-don't-care-what-you-think attitude. Her 2002 debut Let Go crashed onto radio with "Complicated" and "Sk8er Boi"—instant anthems—and positioned her as the voice of a generation of mall-goers who wanted to be skaters but shopped at Abercrombie. Follow-ups Under My Skin and The Best Damn Thing kept her reign solid through 2007.
Avril Lavigne broke through in 2002 with "Let Go," an album that seemed engineered to capture every restless teen's inner monologue. The two lead singles became massive: "Complicated" (aimed at phoniness and fake people) and "Sk8er Boi" (the perennial underdog love story) were omnipresent on MTV, at school dances, and in LiveJournal profiles. Her look—deliberately tomboyish, punk-influenced, effortlessly cool in a calculated way—became the template for early-2000s teen fashion.
By the mid-2000s, with "Under My Skin" (2004) and especially "The Best Damn Thing" (2007, which gave her her first Hot 100 number-one with "Girlfriend"), Avril had cemented herself as a crossover star: pop-punk credentials, radio-friendly production, and a refusal to play the ingénue. Her peak lasted roughly 2002–2007, after which pop moved on, but the cultural imprint—the tie, the aesthetic, the attitude—stuck around as a defining artifact of the era.
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Britney Spears
A former Mickey Mouse Club kid whose debut single '...Baby One More Time' (September 1998) and January 1999 album catapulted her to megastardom as the defining pop voice of the millennium. TRL countdown staple, Rolling Stone covers, Pepsi deals, and cultural omnipresence through the early 2000s with 'Oops!... I Did It Again' (2000) and 'Toxic' (2003–04).
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Linkin Park — Hybrid Theory
Linkin Park's landmark debut album, released October 24, 2000, blending Chester Bennington's soaring vocals with Mike Shinoda's aggressive rapping over heavy guitars and electronic production. The best-selling album of 2001 in the US, Hybrid Theory became the soundtrack to countless angsty bedrooms and defined nu-metal for a generation.
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Michelle Branch — "Everywhere"
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.
Vanessa Carlton — "A Thousand Miles"
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.