Singing as a warm-up act at a local lip-synching contest, 8-year-old Timberlake wows the crowd with his version of a New Kids on the Block tune. "Little girls in the sixth, seventh, eighth and ninth grades just surrounded him," Timberlake's stepfather, Paul Harless, later tells PEOPLE. "It was like something out of a Beatles movie. They had him pinned against a wall. Some wanted to get his autograph; some tried to give him money."
Wearing a cowboy hat and western shirt, 11-year-old Timberlake sings Alan Jackson's "Love's Got A Hold On You" as a contestant on TV's Star Search. He loses.
Timberlake, 14, teams up with Chris Kirkpatrick and dancer Joey Fatone before recruiting former Mouseketeer Chasez. Timberlake's vocal coach suggests daycare-worker Lance Bass, rounding out the quintet. The boys become 'N Sync, a name coined by Timberlake's mother, Lynn Harless, who rearranged the last letter of each member's first name. Boy-group wranglers Lou Pearlman and Johnny Wright, the same duo that launched the Backstreet Boys and late '80s group New Kids on the Block, manage the group.
'N Sync scores a recording contract with German label BMG. Their self-titled debut album is released in Europe and becomes an instant phenomenon thanks to singles "I Want You Back" and "Tearin' Up My Heart." 'N Sync spends the next two years touring abroad before the album's U.S. in 1998, where it sells 5 million copies by the year's end.
Britney Spears denies that she is dating Timberlake. "We're just friends," she tells PEOPLE, adding that she is too busy touring – and getting over her first serious relationship – to get involved. The pair has been friends since the The New Mickey Mouse Club, when he was 12 and she was 11.
'N Sync's No Strings Attached sells 1.1 million copies on its first day and a record-breaking 2.4 million within the first week. The album earns the boy band three Grammy nods, including Record of the Year for "Bye, Bye, Bye."
Although they have denied their romance for more than a year, Timberlake and Spears finally acknowledge they are a couple when a New Orleans Times-Picayune reporter spots them kissing at a local lounge. PEOPLE dubs the twosome "the first couple of pop."
'N Sync releases its fourth album, Celebrity, and though it never reaches the success of No Strings Attached, the album does peak at No. 1 on Billboard's 200 chart. The key singles are the breakup ballad "Gone" and the heavily R&B-influenced "Girlfriend," which signals the group's turn toward hip-hop and gets them airplay on urban radio stations.
Timberlake's mom tells PEOPLE that her son and Spears "have hit a rough spot." But it's not until June that they announce their break-up. "That's a struggle. I fight these two people inside of me," he tells Teen People. "One's completely jaded, [saying], 'If you throw your heart back out there it's going to be horrible.' The other part says, 'Why not?'"
BIOGRAPHY (top to bottom): WILLARD G. TRESSEL; Everett; KIM TONELLI/CORBIS; amazon.com; TAMMIE ARROYO/AFF; Kevin Mazur; Jeff Vespa/Wireimage