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.
The Backstreet Boys were formed in 1993 in Orlando by music impresario Lou Pearlman: Nick Carter, AJ McLean, and Howie Dorough from Florida, plus Kentucky cousins Brian Littrell and Kevin Richardson. They broke big in Europe first; the US caught up when their self-titled 1997 debut album went multi-platinum. Their true peak arrived with Millennium (1999), featuring the career-defining single "I Want It That Way"—one of the most recognizable pop songs of the era.
From 1996 through 2001, the Backstreet Boys dominated youth culture: MTV played their videos on heavy rotation (with TRL making them daily fixtures from its 1998 debut), radio couldn't play "I Want It That Way" enough, and sold-out world tours filled arenas with screaming fans. Black & Blue (2000) closed out the run at the top, with the group and rivals NSYNC—also a Pearlman product—defining the boy-band arms race that shaped pop for a decade. The group never actually broke up and still tours, trading on exactly this era.
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Backstreet Boys — "I Want It That Way"
The boy-band anthem that became iconic despite its infamously nonsensical lyrics, which even Kevin Richardson admitted "really doesn't make much sense." Peaked at number six on the Hot 100 due to chart technicalities, but hit number one in over twenty-five countries and spent ten weeks atop the US Adult Contemporary chart—Rolling Stone later ranked it among the 500 greatest songs of all time.
Backstreet Boys — "Everybody (Backstreet's Back)"
The song that announced the arrival with attitude—released July 1997, it became the MTV template for boy-band spectacle when director Joseph Kahn shot the legendary haunted-mansion video where each member transformed into a classic horror monster. The production cost a reported million dollars, the choreography was airtight, and the "Am I original? Yeah!" call-and-response became instantly quotable.
Backstreet Boys — "As Long as You Love Me"
The sweeping mid-tempo ballad that showcased the softer side of the BSB formula—all yearning strings and harmonies, shipped to radio without a physical single. Ineligible for the Hot 100 under 1990s chart rules, it still became a top-three hit across the world, and that folding-chair choreography in the music video became instantly iconic.
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).