Britney Spears and Justin Timberlake’s Relationship: Photos

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April 15, 2020 7:35PM EDT
Justin Timberlake and Britney Spears 'Crossroads' film Premiere, Los Angeles, America - 11 Feb 2002 02/11/02 Hollywood, CA Justin Timberlake and Britney Spears at the premiere of Paramount Pictures' "Crossroads". The premiere was held at the Grauman's Chinese Theatre in Hollywood. Photo®Eric Charbonneau/BEI
Bei/Shutterstock

Britney Spears and Justin Timberlake dated from 1999 until 2002. See their pics here.

Britney Spears and Justin Timberlake originally met as kids in in 1991 on the set of Disney’s popular variety show, ‘The Mickey Mouse Club’. As teens, the duo both pursued singing careers with Britney later touring with NSYNC after the release of her first album ‘Baby One More Time’. Britney and Justin struck up a romance shortly after, and went on to become one of the most beloved celebrity couples of all time. The duo were a red carpet fixture at music award shows throughout the late ’90s and early ’00s, iconically rocking matching denim outfits to the 2001 American Music Awards. Sadly, Britney and Justin called things quits in 2002 after a rumored cheating scandal, which later inspired Justin’s memorable song ‘Cry Me A River.’

Justin and Britney’s relationship was thrown back into the spotlight in 2023 with the release of Britney’s memoir. Britney claimed in her book that she had an abortion after Justin got her pregnant. She also alleged that Justin cheated on her with “another celebrity” when they were dating. Justin has not verified these claims.

Click through the gallery to see some of Britney and Justin’s most romantic moments!

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Justin Timberlake & Britney Spears at the ‘Crossroads’ premiere

Justin Timberlake & Britney Spears at the ‘Crossroads’ premiere
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Britney Spears, right, shares a sweet laugh with her then-boyfriend Justin Timberlake at the Los Angeles premiere of her film ‘Crossroads’ in Feb. 2002. The couple looked so in love as they arrived together and posed for photos.

April 15, 2020, 6:53PM
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Justin Timberlake arrives with Britney Spears at the ‘Crossroads’ premiere

Justin Timberlake arrives with Britney Spears at the ‘Crossroads’ premiere
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Britney Spears and Justin Timberlake are so in love as they sweetly hold hands at the premiere for her first-ever theatrical film ‘Crossroads’ at the Grauman’s Chinese Theatre in Los Angeles on Feb. 11, 2002. The film, also starring Zoe Saldana and Taryn Manning, followed the story of three teen girls on a road trip.

April 15, 2020, 6:52PM
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Britney Spears & Justin Timberlake have a candid moment on a red carpet

Britney Spears & Justin Timberlake have a candid moment on a red carpet
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Britney Spears and Justin Timberlake return to the American Music Awards in 2002. The couple are seen here having a candid moment on the red carpet at the Shrine Auditorium. Britney stunned in a low cut pink sequin dress, while Justin opted for a cool black leather jacket.

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Britney Spears & Justin Timberlake attend a party

Britney Spears & Justin Timberlake attend a party
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Britney Spears and Justin Timberlake are spotted attending a private family celebration at the Regent Beverly Wilshire Hotel on April 1, 2001. The couple looked ready for an evening on the town, with Britney rocking a slinky beige slip dress and Justin in a sequin blazer and see-through button down.

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Britney Spears & Justin Timberlake’s iconic denim outfits

Britney Spears & Justin Timberlake’s iconic denim outfits
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In perhaps their most memorable red carpet moment, then-couple Britney Spears and Justin Timberlake arrive at the 2001 American Music Awards. The couple rocked matching head-to-toe denim ensembles, which also included a cowboy hat for Justin. ‘You do a lot of things when you’re young and in love,’ Justin said of the look nearly 20 years later in an interview with former bandmate Lance Bass.

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Britney Spears celebrates the launch of her third album

Britney Spears celebrates the launch of her third album
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Britney Spears and Justin Timberlake arrive for the launch party of her third album ‘Britney’ at Centro Fly in NYC on Nov. 6, 2001. The couple looked so in love as they snuggled for photographers on the red carpet. With provocative lead single and video ‘Slave 4 U’, the album was a departure from the bubblegum pop of Britney’s first two albums.

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‘Saturday Night Live’ after party at the Sarafina Restaurant

‘Saturday Night Live’ after party at the Sarafina Restaurant
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Britney Spears and Justin Timberlake arrive hand-in-hand to ‘SNL’s after party at NYC’s Serafina Restaurant on Feb. 2, 2002. The party followed Britney’s first-ever hosting gig on the long running NBC sketch program, where she also pulled double duty as musical guest.

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Justin Timberlake & Britney Spears hold hands at the ‘Crossroads’ premiere

Justin Timberlake & Britney Spears hold hands at the ‘Crossroads’ premiere
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Britney Spears and Justin Timberlake are all-smiles as they arrive hand-in-hand for her ‘Crossorads’ premiere in Los Angeles on Feb. 11, 2002. The ‘Oops!…I Did It Again’ singer memorably rocked a blush pink cap and low cut ruffle top for the occasion.

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Justin & Britney arrive at a ‘Crossroads’ screening

Justin & Britney arrive at a ‘Crossroads’ screening
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Justin Timberlake and Britney Spears arrive at Planet Hollywood in New York City on Feb. 13, 2002 for a screening of her first film ‘Crossroads.’ Zoe Saldana and Taryn Manning starred alongside Britney in the teenage coming of age film, whuch featured the trio going on a road trip.

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Britney Spears and Justin Timberlake play at a charity basketball game

Britney Spears and Justin Timberlake play at a charity basketball game
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Justin Timberlake and Britney Spears are seen on the basketball court of a charity celebrity competition. The couple memorably rocked jerseys that read ‘Pinky’ and ‘Stinky’ on the back — their respective nicknames for each other. Justin’s number was 1 1/2, which Brit completed as a 1/2.

April 15, 2020, 6:52PM