Britney Spears & Justin Timberlake’s Dating Timeline: From The ‘Mickey Mouse Club’ To Their Breakup & Through Today

• Britney Spears and Justin Timberlake dated from 1999 to 2002 during their aboriginal days of fame
• After the split, helium painted Britney arsenic a cheater successful interviews and his “Cry Me A River” video
• Justin publically apologized to Britney aft her struggles were the taxable of a 2021 documentary

Britney Spears and Justin Timberlake were axenic popular royalty successful the precocious ’90s and aboriginal aughts, truthful people’s obsession with their narration comes arsenic nary surprise. The “Baby One More Time” singer, 40, and NSYNC frontman, 41, seemed similar they were cleanable for each different erstwhile they went nationalist successful 1999. It was each cute soundbites and PDA-packed reddish carpet appearances until things came crashing down successful 2002, amid rumors of cheating and lies.

After the breakup, Justin mocked his ex successful euphony videos and began openly talking trash astir her, adjacent arsenic her intelligence wellness appeared to suffer. (“Cry Me A River” is honestly creepy successful hindsight, and we each retrieve however helium was Mr. Kiss-and-Tell successful that TMI-packed 2002 Hot97 vigor interview.)

Britney Spears and Justin Timberlake’s narration is inactive talked about, contempt the information they divided successful 2002. (MEGA)

Both singers would determination connected romantically — Justin wed Jessica Biel, 40, successful 2012 and Britney joined histrion Sam Asghari, 28, successful 2022 — but the bitterness would remain. It took astir 2 decades for the “SexyBack” vocalist to finally apologize to his ex, seemingly prompted by a surge of enactment for the prima amid her 2020s-era conservatorship battle.

So is everything bully betwixt Britney and Justin now? Take a look backmost astatine the exes’ romance and wherever their narration stands present successful our timeline, close here.

Britney & Justin Meet: 1992

In 1992 Britney and Justin were some formed successful The All-New Mickey Mouse Club. At the time, Britney and Justin were astir 11 years old. The amusement besides featured aboriginal stars Christina Aguilera and Ryan Gosling and ran from 1993 to 1996.

The formed of ‘The All-New Mickey Mouse Club.’ (Everett)

Following the series, Britney returned to Mississippi. She yet came backmost to New York City to prosecute her singing career, however. Justin, meanwhile, was recruited arsenic a subordinate of the lad set NSYNC.

Though they parted ways, the songstress seemed to person near an content connected Justin. He told GQ successful 2006, “I was successful emotion with her from the start. I was infatuated with her from the infinitesimal I saw her.”

Britney & Justin Start Dating: 1999

Justin and Britney started dating successful 1999. (MEGA)

Fame yet reunited Britney and Justin eventually, who began dating successful 1999 arsenic some of their careers began taking off. Talking astir their transportation with The Observer successful 2001, Britney, “We’ve gone done truthful overmuch unneurotic and we’ve known each different since we were 12 years old. We cognize each different wrong and out.”

Britney & Justin’s Iconic AMAs Looks: Jan. 2001

As their narration progressed, Justin and Britney became reddish carpet regulars. One of the couple’s astir iconic moments came astatine the American Music Awards successful January 2001, conscionable weeks earlier their associated Super Bowl performance. While walking the reddish carpet, Justin and Britney wore matching, head-to-toe denim outfits.

Justin and Britney astatine the 2001 American Music Awards. (AP)

In the years since the brace walked the reddish carpet together, some person commented connected the manner choice. In a 2021 interrogation with The Hollywood Reporter, Justin admitted helium had immoderate manner “regrets” from his aboriginal years. “I confess that determination was possibly a play successful the ’90s wherever I could skip implicit immoderate of the outfits that were public,” helium shared.

Britney, connected the different hand, looked backmost connected the infinitesimal fondly. “I conjecture my denim was a deed years ago,” Britney commented connected a photograph of 2 toddlers recreating the outfit backmost successful Aug. 2020.

Britney & Justin Play The Super Bowl: Jan. 2021

With some stars astatine the apical of their game, it was lone a substance of clip earlier they shared a monolithic stage. Fans of Britney and Justin were treated to a associated show by the brace astatine the Super Bowl XXXV halftime amusement connected Jan. 28, 2001.

Justin and Britney execute with Aerosmith and much and the 2001 Super Bowl halftime show. (AP)

NSYNC joined stone set Aerosmith connected signifier for a medley, earlier Britney and a slew of stars (Mary J. Blige and Nelly, among them) joined for a rendition of Aerosmith’s deed with Run DMC “Walk This Way.” The show was wholly electric, solidifying some stars’ spot successful popular history.

Justin & Britney At The ‘Crossroads’ Premiere: Feb 2022

Britney and Justin astatine the premiere of ‘Crossroads’ successful 2002. (AP)

In February 2002, Justin supported Britney astatine the premiere of her film Crossroads, co-starring Zoe Saldana and Taryn Manning. The 2 looked ace cute unneurotic and held hands connected the reddish carpet. Sadly, this was 1 of the past nationalist appearances the 2 would marque unneurotic earlier they went their abstracted ways.

Britney & Justin Breakup: Mar. 2002

Britney and Justin’s narration ended successful aboriginal 2002, but the mates didn’t instantly publicize the split. The “Overprotected” vocalist was the archetypal to interruption the quality during an quality connected Britain’s “Big Breakfast” successful Mar. 2002, arsenic reported by CNN. “I would not accidental I was successful an aggravated narration with anyone astatine the moment,” she dished astatine the time. “I’m azygous close now.”

The tabloids hounded the exes astir the breakup for months after, during which clip Justin began to signifier his broadside of the story. He told Barbara Walters successful a Nov. 2002 ABC interview, “I retrieve erstwhile we decided we were going to spell our abstracted ways, we sat down and I said to her, ‘If there’s ever a infinitesimal wherever you ever request me, you tin remainder assured that I volition beryllium determination due to the fact that I emotion you arsenic a idiosyncratic and I volition ever emotion you.” Sparking adjacent much gossip, helium told Barbara helium “promised” Britney helium wouldn’t stock what “specifically” pb to the split. Way to permission everyone hanging.

Though helium tried to play the bully feline astir of the time, Justin besides tried to slut-shame Britney by sharing lurid details astir their enactment beingness together. One of the astir infamous instances was during an quality connected The Star & Buc Wild Morning Show successful Nov. 2002, wherever helium admitted to sleeping with Britney, contempt the information some publically pledged to enactment virgins until marriage.

Justin Releases ‘Cry Me A River’: Dec. 2002

Justin released the opus “Cry Me A River” astatine the extremity of 2002, seeming the laic bare his heartbreak pursuing the Britney split. The play lone intensified aft the euphony video dropped successful Dec, featuring a Britney Spears look-alike and a beardown proposition that Miss Spear’s cheated.

Britney Releases ‘Everytime’: 2003

Britney appeared to respond to the way with her ain ballad successful 2003. “Everytime,” a azygous disconnected of her medium In The Zone, showed disconnected Britney’s much contemplative, soulful side.

The vocalist has ne'er confirmed oregon denied that the opus is astir her erstwhile flame, though fans to this time work into the lyrics similar “Why are we strangers/When our emotion is strong?” arsenic being astir Justin.

Britney’s Diane Sawyer Interview: Nov. 2003

Despite wanting to determination connected from her high-profile romance, Britney was inactive pressed astir the extremity of her narration with Justin. She sat down with Diane Sawyer for a Primetime interview successful Nov. 2003, wherever the writer pushed Britney to admit what she “did” to extremity the romance.

Britney Spears sat down for a “Primetime” interrogation with Diane Sawyer successful 2003. (MEGA)

“He has gone connected tv and beauteous overmuch said you broke his heart,” Diane said. “You did thing that caused him truthful overmuch pain, truthful overmuch suffering — what did you do?” Britney was noticeably shaken by the questions and began crying during the interview.

The speech was featured successful the documentary Framing Britney Spears, causing Britney’s loyal fans to request an apology from Diane. Britney called out the quality anchor straight successful a Dec. 2021 Instagram post. She slammed Diane for “forcing” her “to talk” and told the interviewer she could “kiss” the singer’s “white a**.”

Justin Writes Another Britney Song: 2006

Justin continued to speech astir the Britney breakup successful the mid-2000s. “I felt similar she had a mates of opportunities to conscionable benignant of instrumentality up for me, and she didn’t,” helium complained to GQ successful 2006. “Which is fine. But astatine that time, you know, I fought back, and that’s the mode I fought back. I utilized my mind. I came up with a song.”

The comments seemed similar a debased stroke astatine the time. While Justin was griping, Britney’s idiosyncratic problems were rapidly escalating. Her matrimony to Kevin Federline ended successful Nov. 2006, specified weeks aft they welcomed lad Jayden successful September 2006. In 2008 she was hospitalized connected a 5150 hold, and a period aboriginal she was placed nether her begetter Jamie Spears’ conservatorship.

Justin Says They Don’t Speak: 2011

Justin looked backmost connected the narration successful a 2011 interrogation with Vanity Fair, admitting it’d been astir a decennary since they past spoke. “We were 2 birds of the feather — small-town kids, doing the aforesaid thing,” helium told the magazine. “But past you go adults and the mode you were arsenic kids doesn’t marque immoderate sense. I won’t talk connected her, but astatine slightest for me, I was a wholly antithetic person. I conscionable don’t deliberation we were normal; determination was thing mean astir our existence.”

Britney & Justin Have ‘No Issues’: 2020

While Britney and Justin surely weren’t besties, a root shed immoderate EXCLUSIVE airy connected the authorities of their narration successful April 2020. “Even though they aren’t going to beryllium hanging retired with each different anytime soon, they person nary issues with each other,” the insider shares. “[They] would beryllium much than blessed to beryllium successful the aforesaid country arsenic each other. They are precise chill with each other.”

Around the aforesaid time, Brit praised her ex for his philharmonic skills connected Instagram. She shared a clip of herself dancing to his song “Filthy,” and wrote, “PS I cognize we had 1 of the world’s biggest breakups 20 years agone …… but hey the antheral is simply a genius. Great opus JT!”

Justin Apologizes To Britney: Feb. 2021

After years retired of the spotlight, the songstress was the halfway of speech erstwhile again aft the merchandise of the documentary Framing Britney Spears successful aboriginal 2021. The doc unpacked Britney’s spot successful popular culture, portion besides taking purpose astatine immoderate of her harshest critics during the 2000s — namely Justin.

The “Bye, Bye, Bye!” vocalist was fundamentally forced to issue a nationalist apology to Britney successful Feb. 2021. In it, helium wrote that helium was “deeply atrocious for the times successful my beingness wherever my actions contributed to the problem.”

He continued, apologizing for times “Where I spoke retired of turn, oregon did not talk up for what was right.” Justin added, “I recognize that I fell abbreviated successful these moments and successful galore others and benefited from a strategy that condones misogyny…I americium profoundly atrocious for the times successful my beingness wherever my actions contributed to the problem, wherever I spoke retired of turn, oregon did not talk up for what was right.”

Justin Supports Britney’s Conservatorship Fight: Jun. 2021

The Justified singer erstwhile again spoke retired successful enactment of Britney aft she spoke retired successful tribunal against her ongoing conservatorship successful summertime 2021. In her 24-minute June testimony, Britney accused her conservators of forcing her to instrumentality beardown psychiatric drugs similar Lithium and refusing to fto her person her IUD removed truthful she could effort to person different child.

After what we saw today, we should each beryllium supporting Britney astatine this time.

Regardless of our past, bully and bad, and nary substance however agelong agone it was… what’s happening to her is conscionable not right.

No pistillate should ever beryllium restricted from making decisions astir her ain body.

— Justin Timberlake (@jtimberlake) June 24, 2021

Justin took to Twitter to support his ex successful a June 23 post, that said, “Regardless of our past, bully and bad, and nary substance however agelong agone it was… what’s happening to her is conscionable not right.” Regarding her wishes to person a baby, helium added that, “No pistillate should ever beryllium restricted from making decisions astir her ain body.”