31 January 2023 , 19:41
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As A-list exes go, birthday boy Justin Timberlake sure has aplenty – from Toxic hitmaker Britney Spears to Spice Girl Emma Bunton – and even Fergie.
The Cry Me A River singer, 42 today, is now settled down with his wife of more than 10 years Jessica Biel, but he has quite the long list of surprising famous flings.
He tied the knot with The Sinner actress Jessica, 40, back in October 2012 after dating on and off for five years, welcoming their son Silas in April 2015.
Despite splitting for a brief period in March of 2011, the pair reconciled the following July and continued their 'happy ever after' love story from that point.
But who has JT dated before settling down with Jessica? Here, we take a look...
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Justin has settled down with actress Jessica (NBCU Photo Bank via Getty Images)Olivia Wilde
It was during Justin and Jessica's break that he became linked to Trolls star Olivia Wilde in April 2011, with a source at the time claiming they were "obviously a couple".
The pair were spotted enjoying each other's company in Los Angeles at the time when an insider told Us Weekly they were "a couple or on a date".
Fergie
Throwing it all the way back to the 90s, before anything serious was going on in Justin's love life, he was linked to Black Eyed Peas member Fergie.
They are reported to have briefly dated from 1996 to 1997, with a source previously telling the Courier Mail: "He was 16 and I was 23. It was before he got real heavy with Britney Spears."
Britney Spears
Justin and Britney dated between 1999 and 2002 (Getty Images)Justin and Britney were an item between 1999 and 2002, they met after appearing on The Mickey Mouse Club.
Only recently, the Toxic hitmaker took to Instagram to discuss their relationship. She posted: "When we used to shoot hoops TOGETHER … that’s when miracles happened."
At the time, fans seemed confused by Britney's post, with one person tweeting: "Now hold on why is Britney Spears posting old pics of her and Justin."
Another added: "Britney out here posting Justin pics now. Omg. Is this 2002?!"
Emma Bunton
Justin reportedly told the press he was dating Emma (Getty Images)
They got together after things ended with Britney (AFP/Getty Images)In perhaps the most surprising additions of Justin's relationship timeline is Spice Girls' Emma Bunton who was linked to Justin way back in 2002.
She has always kept quiet about "hanging out" with the musician, but she did spill a little after Justin reportedly revealed their link to the News of the World.
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Chat show host Jonathan Ross previously asked Emma if she really had a "one-nighter" with Justin, to which she replied: "Jonathan!"
She explained at the time: "We hung out and partied a bit and he was very sweet." The brief stint reportedly only lasted a few weeks.
Cameron Diaz
Justin dated Cameron between 2003 and 2006 (Getty Images)
They later reunited for Bad Teacher in 2011 (WireImage)Justin dated Cameron Diaz between 2003 and 2006 before they later reunited for Bad Teacher in 2011, with Cameron admitted they've "always had a good laugh".
In a previous interview she said: "To make a movie where we get to have a laugh together, and there really was no one else who was more perfect for this part."
She told Us Weekly in 2011: "It really wasn’t a big deal, we had a great time and did the job, and we do what all actors do afterward: We all go our separate ways."
Justin and Jessica welcomed son Silas in April 2015 (Getty Images)Also, after his split from Britney and just before linking up with Cameron, Justin dated his backup dancer Jenna Dewan.
Speaking on Watch What Happens Live With Andy Cohen back in 2017, she confirmed: "We dated, not that long. We were like friends … that dated."
Justin has also reportedly "hooked up several times" with The Avengers: Endgame star Scarlett Johansson "over the years" after she starred in his What Goes Around music video.