Britney Spears and Justin Timberlake are one of pop culture’s most iconic couples of all time.
The Princess of Pop and *NSYNC member once shared what seemed to be a picture-perfect romance from the outside, but new details in Spears’ bombshell memoir, “The Woman in Me,” reveal that the young lovebirds dealt with real-life tragedies throughout their three years together.
Here’s everything you need to know about Spears and Timberlake’s relationship – and the drama that succeeded their split years later.
1993 to 1996: They meet on the “All-New Mickey Mouse Club” and puppy love ensues
Spears and Timberlake met in 1993 when they were cast to star in the revamped “All-New Mickey Mouse Club,” performing song covers and acting skits at just 12 years old.
The Louisiana native – along with future pop star Christina Aguilera – had a crush on the curly-haired kid from Tennessee.
Timberlake allegedly gave Spears her first kiss during a game of Truth or Dare while at sleepover amid filming for the Disney show, she later revealed in her memoir.
However, the adolescents parted ways after the show wrapped to briefly return to a life of teenage normalcy and later chase pop superstardom.
December 1998: They reconnect when Spears joins *NSYNC on tour
Soon after the “Mickey Mouse Club” ended, Timberlake formed the legendary boy band *NSYNC with bandmates JC Chasez, Chris Kirkpatrick, Joey Fatone and Lance Bass.
In 1997, the group released “Tearin’ Up My Heart,” which led to them garnering a huge following in America. A year later, rising pop princess Spears came out with her debut single, “… Baby One More Time.”
Spears joined *NSYNC as one of their opening acts for their *NSYNC in Concert tour from late 1998 to early 1999, where it appears that she and Timberlake rekindled their friendship and later their romance.
1999: Spears and Timberlake confirm they are dating
By 1999, Spears and Timberlake had already sparked romance rumors, but the “Sometimes” singer was not yet ready to spill the details about their bond.
She told Rolling Stone for her iconic cover story in April of that year that she was focusing on work and had “no feelings at all.”
However, according to multiple outlets, the pair confirmed they were indeed a couple sometime that year.
January 2001: The darling duo turns heads in denim at the American Music Awards
Spears and Timberlake caught people’s eyes whenever they walked a red carpet together, but they especially turned heads when they arrived at the 2021 American Music Awards in matching denim outfits.
The cute couple’s now-iconic looks have since been recreated by tons of fans and a few famous faces like Katy Perry, Riff Raff and Camila Cabello.
January 2001: Spears and Timberlake perform together at Super Bowl XXXV
By 2001, Timberlake and Spears were mega-stars in their own right, but they had the opportunity to share a career milestone when they hit the stage together for the Super Bowl XXXV Halftime Show.
They performed alongside a star-packed roster that included the rest of *NSYNC, Aerosmith, Mary J. Blige and Nelly.
March 2002: Spears and Timberlake break up after three years together
In early 2002, rumors circulated that Spears and Timberlake had called it quits. However, the “Slave 4 U” singer confirmed the split for the first time while promoting her film, “Crossroads,” in London that March.
According to Entertainment Weekly, she said during a press conference at the time, ”I would not say I was in an intense relationship with anyone at the moment.”
Spears then told the British TV show ”Big Breakfast” two days later, ”I’m single … right now.”
Nov. 1, 2002: Timberlake breaks his silence on the breakup
After telling People magazine that he had a “broken heart,” Timberlake sat down with the now-late Barbara Walters to talk about the split on “20/20.”
He called his defunct relationship “young love” but also stated that it had been “very intense.”
At the time, Spears had allegedly vowed to wait to have sex before marriage. Walters asked Timberlake point blank whether he and Spears abstained, to which he responded with a laugh, “Sure … sure.”
Nov. 25, 2002: Timberlake fuels cheating rumors with “Cry Me a River” music video
Timberlake sparked a lot of chatter when he released his single “Cry Me a River” in October 2002, but fueled the rumor mill even more when he hired a Spears look-alike for the breakup song’s music video.
The track’s lyrics state, “You don’t have to say, what you did / I already know, I found out from him.”
The song became a certified hit, peaking at No. 3 on the Billboard Hot 100 chart, and led many to turn on Spears for the role she seemingly played in the demise of the once storybook romance.
August 2003: Spears kisses Madonna at the VMAs – shocking Timberlake
When the 2003 MTV Video Music Awards were taking place, fans were wondering how Spears and Timberlake would react during one of their first public run-ins post-breakup.
When Spears hit the stage alongside Madonna and Aguilera to perform a rendition of “Like a Virgin” during the award show, she leaned over and gave the Queen a Pop a seductive smooch.
The cameras immediately panned to Timberlake to see his reaction, which showed the “SexyBack” singer with a stern look on his face.
2003: Spears breaks down into tears when speaking to Diane Sawyer about the split
Spears sat down with Diane Sawyer to share her side of the breakup story in 2003, but instead of being treated as “heartbroken,” many thought the “Toxic” singer was villainized throughout the ABC interview.
“You broke his heart, you did something that caused him so much pain, so much suffering,” Sawyer asked Spears at the time. “What did you do?” At one point, the then 21-year-old started crying.
In 2021, Spears called out Sawyer via social media for how she was treated, writing in part at the time, “I was a baby… I was almost 22 and didn’t understand, but I f—king do now.”
2004: Spears releases her own breakup song, “Everytime”
Spears confessed in her interview with Sawyer that she was “going through a lot emotionally” when she wrote “Everytime.”
The lyrics for the melodic track read, “I may have made it rain / Please, forgive me / My weakness caused you pain / And this song’s my sorry.”
In the video, Spears depicts a tumultuous relationship amid tabloid drama. Years after its release, fans questioned the true meaning behind the music video given a shocking revelation in Spears’ book.
2013: Timberlake seemingly calls Spears a “bitch” – and then denies it
Timberlake caught flack in 2013 for reportedly slamming Spears at a pre-Super Bowl concert.
“Sometimes in life, you think you found the one. But then one day you find out that she is just some bitch,” he reportedly said before belting out “Cry Me a River” at a show in New Orleans.
That year, Spears released “Scream & Shout” with Will.i.am., in which they sing, “You are now now rocking with Will.i.am and Britney bitch,” which is why many believed Timberlake had referenced his ex.
However, the “Lovestoned” singer denied the allegations, tweeting at the time, “Wouldn’t disrespect ANYONE personally. Ever. #Relax #ItsBritneyBitch I do love that saying though *with accent* #Respect”
2020: Spears calls Timberlake a “genius” while praising his music
Spears shocked many of her followers when she posted a video of herself dancing to her ex’s song “Filthy” in April 2020 and called him a “genius.”
She wrote via Instagram at the time, “PS I know we had one of the world’s biggest breakups 20 years ago, but hey the man is a genius !!!! Great song JT”
February 2021: Fans turn on Timberlake after paramount Spears documentary
The New York Times released the groundbreaking documentary “Framing Britney Spears” in February 2021, which made many viewers see the highs and lows of Spears’ career in a new light — including her breakup from Timberlake.
The series caused Timberlake to get slammed on social media for his past remarks, which many deemed to be “misogynistic.”
The “Mirrors” singer, however, quickly issued a mea culpa. He apologized to Spears, writing in part, “I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn, or did not speak up for what was right.”
June 2021: Timberlake supports Spears amid her #FreeBritney battle
In June 2021, Spears gave a heart-wrenching court testimony that lasted 23 minutes about her more than a decade-long controversial conservatorship.
Her words moved many celebs, including Timberlake, who tweeted at the time that we should “all be supporting” the “Piece of Me” singer.
“Regardless of our past, good and bad, and no matter how long ago it was… what’s happening to her is just not right,” he added at the time.
“No woman should ever be restricted from making decisions about her own body.”
March 2022: A newly-free Spears calls out Timberlake via social media
After her conservatorship was terminated in November 2021, Spears found her voice once again.
She’d often lash out at family members and other people who hurt her in the past – including Timberblake.
Spears wrote of the “What Goes Around … Comes Around” singer, “He served with his first album using your name claiming you did him dirty!!!!”
October 2023: Timberlake worries about Spears’ memoir and she drops a bomb
After Spears announced the release date for her highly anticipated memoir, “The Woman in Me,” sources told Page Six exclusively that Timberlake was “concerned” about what she may have written about him.
“He’s very curious what she’ll reveal from their relationship,” a source previously said. “It’s eating at him.”
Spears then shockingly revealed in an excerpt released via People shortly after that Timberlake allegedly persuaded her to get an abortion when they were together.
“I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I’d anticipated,” the “I’m Not a Girl, Not Yet a Woman” singer wrote in her book.
“But Justin definitely wasn’t happy about the pregnancy. He said we weren’t ready to have a baby in our lives, that we were way too young.”
Spears went on to claim, “I’m sure people will hate me for this, but I agreed not to have the baby. I don’t know if that was the right decision. If it had been left up to me alone, I never would have done it. And yet Justin was so sure that he didn’t want to be a father.”
