![Singers Britney Spears and Justin Timberlake in the audience at the 2000 MTV Music Video Awards in New York](https://cdn.statically.io/img/people.com/thmb/AJZe1BTjuQY0D-VBmadOAifdHDA=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(716x180:718x182)/Britney-spears-justin-Timberlake-101723-tout-02f8ff25728f42c3891c003d6900c938.jpg)
Dave Hogan/Getty
Justin Timberlake and Britney Spears' pop-star-perfect romance 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
![Grab Cut Insert Cut 570914 13339#pt1_everett_cr](https://people.com/thmb/5pXp3GuSRuk0GjmC5acJyjX2KM4=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(590x0:592x2)/ryan-gosling-957ec13ac4c34cda9a290959fd281dc9.jpg)
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
![Britney Spears throwbacks](https://people.com/thmb/cOMpqwAvJiulGFlEcbXElARZ3kc=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(999x0:1001x2)/britney-spears-throwbacks-4-8a4763fc07df499d8f6058e476c53153.jpg)
Justin interviewed Britney on the red carpet at the 2000 Grammys.
Cozying Up
![Britney Spears, Justin Timberlake](https://people.com/thmb/bHUT_ZWXwFna76lUTXvi29ICh7o=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(999x0:1001x2)/britney-spears4-2089ab04bae54fd08c7097f460d015a8.jpg)
Timberlake's sweater was made of boyfriend material at the 2000 MTV Video Music Awards.
The Double Denim Seen 'Round the World
![Britney Spears and Justin Timberlake, backstage at the 28th annual American Music Awards](https://people.com/thmb/f0bAZVKi_3BtqFeeaYCc1cg6YJQ=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(655x0:657x2)/britney-spears-2-1-fa7b1d8158d54e818287b6f22458d92b.jpg)
An iconic image from an iconic couple, the pair wore these matching denim get-ups to the 2001 American Music Awards.
Play Ball
![Britney Spears throwbacks](https://people.com/thmb/ZMmKYeS6lJCAXdKIMXbaH-hYsHw=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(999x0:1001x2)/britney-spears-throwbacks-6-209de2768e474ab190b023201b8aa54d.jpg)
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 Spears and Justin Timberlake](https://people.com/thmb/1hP1kYwdoltmyO9k8oBFq_5kNk0=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(680x0:682x2)/gettyimages-75495515-1-854793ef301f41998871c419ac847222.jpg)
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
![Britney Spears and Justin Timberlake,](https://people.com/thmb/2tgcYWjEgpobx6iDweSvL7gz1lU=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(638x539:640x541)/gettyimages-97278334-1-0fffbb05323c4a4a98bcc742c6f1607c.jpg)
In November 2001, Justin was on hand to support his girlfriend at the release of her latest album, Britney.
Power Couple
![Britney Spears and Justin Timberlake](https://people.com/thmb/u9prJ1cDcPTTDuJo9eHruPKavqQ=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(602x0:604x2)/gettyimages-104927381-1-6b296ff27f24494b9d8636666cb659af.jpg)
The duo both embodied early aughts style at a 2001 event.
To a T
![Britney Spears and Justin Timberlake](https://people.com/thmb/Hf5FHZMJlewYIwwsOdUDeLHyMG4=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(665x0:667x2)/gettyimages-76114916-1-25d9d87e98824920a16470c34c4ce837.jpg)
Britney and Justin cuddled up at the MTV Icon Tribute to Janet Jackson.
Super Bowl Superstars
![Britney Spears and Justin Timberlake](https://people.com/thmb/hRRzv0ezKzUmVOEhan-b6WZ6cMs=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(999x0:1001x2)/gettyimages-2280656-76614edd9f1d4103850367f0807ba4b5.jpg)
Britney , along with Justin's band *NSYNC, joined Aerosmith, Nelly and Mary J. Blige at the 2001 Super Bowl halftime show.
Rocking the Stage
![Justin Timberlake, Britney Spears](https://people.com/thmb/FEtozcz_w5QcMH7mfs3wz37F01s=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(939x794:941x796)/britney-spears-justin-timberlake-1-765678b9d048428b8029c6e1c5360a2c.jpg)
And the dynamic duo seemed totally in sync (pun intended) while rocking the stage together.
Live from New York!
![Britney Spears, Justin Timberlake](https://people.com/thmb/-JWExXCrByS8k2s-QOAoTfRRl-A=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(999x0:1001x2)/gettyimages-138455455-1-5a22af3f93c440f8acafcc73c6e6cff1.jpg)
In February 2002, just a month before their split, the pair appeared on Saturday Night Live together.
Premiere Date
![Britney SPEARS and Justin Timberlake](https://people.com/thmb/qMu4ZmpoPpNvT1BJZmpkHCKXspQ=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(700x0:702x2)/gettyimages-86095500-1-81a9669727ac40a593680ff1e19ebe63.jpg)
Justin was there to support Britney at the premiere of her 2002 movie Crossroads in Los Angeles.
New York Minute
![Britney Spears and Justin Timberlake](https://people.com/thmb/aUnIRBg7xYuK-ZR57-eo2fRd8co=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(600x0:602x2)/gettyimages-112374160-1-7064c6b7324d4dbd8a0b9faed34ab355.jpg)
He also accompanied her to the film's premiere in New York City.
Suit and Tie
![Britney Spears and Justin Timberlake](https://people.com/thmb/A3ISQDSOQ2kGcNE-ezDY-K-j-Ms=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(696x0:698x2)/gettyimages-108640000-1-6f6036335cba44699b68774387ae1dc6.jpg)
Before announcing their split in March 2002, the pair attended the Grammys in late February.
Young Love
![Justin Timberlake & Britney Spears during Super Bowl XXXVI - Britney Spears & Justin Timberlake Host Super Bowl Fundraiser at Planet Hollywood Times Square at the Planet Hollywood Times Square in New York City, NY](https://people.com/thmb/Np2-Iew7RhxysUAwXReRiUdbsrA=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(979x753:981x755)/britney-spears-justin-timberlake-5-a748e86a2b884360901c15727108c9e8.jpg)
The baby-faced singers looked young and in love while posing for a photo.
Love and Basketball
![Rodney Jerkins, Chris Tucker, Justin Timberlake, Britney Spears, and Chris Kirkpatrick at the "NBA All-Star Game" at the First Union Center in Philadelphia, Pa. 2/10/02](https://people.com/thmb/IztYIcuxohgaUc14ruTcYGjja_U=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(772x161:774x163)/Britney-spears-justin-Timberlake-101723-2-5d1789eb2f7641eb86b987d9969307a5.jpg)
Scott Gries/NBAE/Getty
Justin and Britney sat alongside Chris Tucker and Chris Kirkpatrick while catching the NBA All-Star game in 2002.
Britney and the Bandmates
![Chris Kirkpatrick, Justin Timberlake, Britney Spears and Joey Fatone](https://people.com/thmb/vJqBouGy0gxN259zBvGIw9J74-4=/4000x0/filters:no_upscale():max_bytes(150000):strip_icc():focal(726x168:728x170)/Britney-spears-justin-Timberlake-101723-1-a751a76abfec4d9f9df9e776555a13d7.jpg)
Jeff Kravitz/FilmMagic
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.