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1989

Taste of Fame

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."

1992

Justin Timberlake

Star Burst

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.

1993

Justin Timberlake

July

Mousing Around

Plucked from a Nashville cattle call, Timberlake wins a prized spot on Disney's TV show The New Mickey Mouse Club, joining Britney Spears, Christina Aguilera, Ryan Gosling, and future 'N Sync band mate, JC Chasez. The show is canceled two years later.

1995

Justin Timberlake

The Boys Are 'N Sync

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.

1996

Justin Timberlake

Tearin' Up the Charts

'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.

2000

Justin Timberlake

Speared by Love

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.

Justin Timberlake

Breaking Records

'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."

Justin Timberlake

October

Definitely a Couple

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."

2001

Justin Timberlake

July 24

A Turn Toward Hip-Hop

'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.

2002

Justin Timberlake

March 27

Britney & Justin Split!

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?'"

Photo Credits

BIOGRAPHY (top to bottom): WILLARD G. TRESSEL; Everett; KIM TONELLI/CORBIS; amazon.com; TAMMIE ARROYO/AFF; Kevin Mazur; Jeff Vespa/Wireimage

Edited by Julia Wang

Justin Timberlake

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