Justin Timberlake
The NSYNC kid who went solo in 2002 and owned the decade. Justified, the Super Bowl, "SexyBack," "Dick in a Box" — by 2007 nobody thought of Justin Timberlake as the boy-band guy anymore.
When NSYNC went on indefinite hiatus in 2002, Justin Timberlake bet on himself and won immediately. His debut album Justified, released in November 2002, opened at #2 on the Billboard 200 with 439,000 first-week copies and went on to sell over 10 million worldwide; "Cry Me a River" and "Rock Your Body" both cracked the top five, and the record earned him two Grammys in 2004, for Best Pop Vocal Album and Best Male Pop Vocal Performance.
February 2004 brought the decade's most replayed live-TV moment: the Super Bowl halftime show with Janet Jackson, where a costume reveal seen by over 140 million viewers briefly exposed Jackson — and Timberlake's apology gave the language a new phrase, "wardrobe malfunction." He absorbed the controversy and kept climbing. FutureSex/LoveSounds, released September 12, 2006, debuted at #1 with 684,000 first-week copies and matched Justified's 10 million-plus worldwide; "SexyBack" spent seven straight weeks at #1, and "My Love" and "What Goes Around... Comes Around" both topped the chart too.
Then he conquered comedy for good measure: the December 2006 SNL digital short "Dick in a Box" won an Emmy for Outstanding Original Music and Lyrics. By decade's end the curly-haired kid from the boy band had become the template for how a pop star graduates.
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NSYNC
'Bye Bye Bye' and its jerky-dancing video were inescapable on TRL, announcing that five boys from Orlando could rival the Backstreet Boys. NSYNC was teen pop's other empire during the late 90s, built by the same producer and fueled by a rivalry that defined a generation.
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).
98 Degrees
The boy band that built itself—assembled independently by four guys chasing the dream in Los Angeles, without a Lou Pearlman or corporate svengali telling them who to be. They cracked the charts with 1997's "Invisible Man," then spent 1998–2000 as Motown Records' R&B-leaning answer to the Backstreet Boys and NSYNC, delivering a handful of genuine hits including one number-one collaboration with Mariah Carey, then watched their moment fade when Nick Lachey married Jessica Simpson in 2002 and reality TV captured his afterlife.
Backstreet Boys
Orlando's harmonizing five-piece formed the template for late-90s teen-pop dominance. The Backstreet Boys' matching choreography and Lou Pearlman's boy-band machinery made them a TRL staple, an arena-tour juggernaut, and the answer to every teen magazine's "Who's your favorite Backstreet Boy?" quiz.