A Look Back at Justin Timberlake & Britney Spears' Relationship in Photos

As teenage superstars, their romance — and subsequent breakup — was headline news. Now their relationship is back in the spotlight thanks to her candid memoir

Justin Timberlake and Britney Spears ' pop-star-perfect romanc e was one of the most defining moments of the early aughts. The former Mouseketeers turned music superstars (she as a solo act, he with *NSYNC) dated from 1999 to 2002 and within those three years, they gave us some of the most iconic moments in pop culture. Spears herself recalled their dramatic breakup (which came with some era-defining songs, including "Cry Me a River"), as "one of the biggest of all time."

Now, their time together is back in the spotlight thanks to Spears' memoir The Woman in Me, in which she recounts their young love, difficult split and the "agonizing" decision to have an abortion after becoming pregnant with his child .

From that denim-on-denim look to performing together, here's a look back at Justin Timberlake and Britney Spears' young romance.

Working for the Mouse

In 1993, Britney Spears and Justin Timberlake (along with Christina Aguilera and Ryan Gosling) joined The Mickey Mouse Club , though it wouldn't be until seven years later that they'd start dating.

Red Carpet Couple

Justin interviewed Britney on the red carpet at the 2000 Grammys.

Cozying Up

Timberlake's sweater was made of boyfriend material at the 2000 MTV Video Music Awards.

The Double Denim Seen 'Round the World

An iconic image from an iconic couple, the pair wore these matching denim get-ups to the 2001 American Music Awards.

Play Ball

The pair had their nicknames for each other, Pinky and Stinky, put on the back of their basketball jerseys for the 3rd annual Challenge for the Children charity event put on by *NSYNC.

Sparkle and Shine

Britney rocked an oh-so-2001 slip dress while Justin wore an also of the time sparkly, pin-striped suit for a night out in Beverly Hills.

Showing Support

In November 2001, Justin was on hand to support his girlfriend at the release of her latest album, Britney .

Power Couple

The duo both embodied early aughts style at a 2001 event.

To a T

Britney and Justin cuddled up at the MTV Icon Tribute to Janet Jackson.

Super Bowl Superstars

Britney , along with Justin's band *NSYNC, joined Aerosmith, Nelly and Mary J. Blige at the 2001 Super Bowl halftime show.

Rocking the Stage

And the dynamic duo seemed totally in sync (pun intended) while rocking the stage together.

Live from New York!

In February 2002, just a month before their split, the pair appeared on Saturday Night Live together.

Premiere Date

Justin was there to support Britney at the premiere of her 2002 movie Crossroads in Los Angeles.

New York Minute

He also accompanied her to the film's premiere in New York City.

Suit and Tie

Before announcing their split in March 2002, the pair attended the Grammys in late February.

Young Love

The baby-faced singers looked young and in love while posing for a photo.

Love and Basketball

Justin and Britney sat alongside Chris Tucker and Chris Kirkpatrick while catching the NBA All-Star game in 2002.

Britney and the Bandmates

The "Baby One More Time" singer posed with three out of the five *NYSNC bandmates (including Chris Kirkpatrick and Joey Fatone) while at the My VH1 Music Awards in 2000.

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