Justin Timberlake is one of the most talented American celebrities alive today. He is a fantastic performer, an incredible songwriter, a talented actor and comedian. On top of all of that, Timberlake has been every girl’s and guy’s heartthrob celebrity crush ever since he stepped into the limelight with boy band, NSYNC back in the 1990s.
I mean, who didn’t have tons of posters of NSYNC and Justin Timberlake hanging up in their room when they were younger? Tearing those things out of J14 was a near-religious experience you shared with your friends in NSYNC’s heyday.
In short, there’s really nothing that this man can’t do. In between musical projects, films and appearances on Saturday Night Live, it turns out that Timberlake has quite the wild romantic history. We can’t say we’re surprised – especially with a handsome face like that.
Much before Justin Timberlake was, well, Justin Timberlake, and before Fergie was performing with the Black Eyed Peas, the two were a couple. Timberlake was only 16-years-old and starting out in NSYNC and Fergie was 23-years-old and part of the pop trio, Wild Orchid. Yikes.
Fergie herself described the relationship: “He was 16 and I was 23…it was before he got real heavy with Britney.”
Britney Spears 1999-2002
The two grew up together on the Disney show, The Mickey Mouse Club, and began a romance in 1999. Remember this matching denim outfit?
I know we probably all wanted to forget about that fashion disaster, but I won’t allow it.
The relationship came to an end in 2002 when Spears allegedly cheated on Timberlake. The rumor inspired Timberlake’s hit song, “Cry Me A River,” which was released on his debut album, Justified.
In 2011, he spoke about the relationship to Vanity Fair. He said, “I just don’t think we were normal; there was nothing normal about our existence.”
Jenna Dewan 2002-2002
Rumors circulated back in 2002 that Jenna Dewan, then a backup dancer for NSYNC, may have played a role in Justin’s breakup with Britney.
Now she’s married to Channing Tatum. That’s one hell of a consolation prize.
Alyssa Milano 2002-2002
Justin Timberlake was on rebound mode when he began dating Milano. When asked about the relationship, Milano agreed that Timberlake was on the rebound. She additionally stated, “That was right after Britney broke his heart. I swooped in for the kill!”
At the time, Milano was 29-years-old and Timberlake was 21-years-old. There’s an interesting pattern emerging here.
Cameron Diaz 2003-2006Jim Spellman/Getty Images.
Cameron Diaz and Justin Timberlake met at the Nickelodeon Kids’ Choice Awards. They were together for three years before the relationship ended. While the two were together, Diaz won a defamation suit against the National Enquirer after the publication announced that Timberlake was cheating on her.
Despite their relationship coming to an end, the two are still close friends and even went on to star in movies together.
Jessica Biel 2007-2011Pascal Le Segretain/Getty Images.
Between 2007 and 2011, Justin Timberlake and Jessica Biel dated – with a few relationship bumps in the road. Biel and Timberlake broke up for a few months in 2011 due to the other women Timberlake was chasing while in a relationship with Biel.
Olivia Munn 2010-2010John Shearer/Getty Images.
One of the supposed reasons that Biel and Timberlake broke up briefly was because he was chasing Munn (amongst other women) and was eventually busted. It was reported that Timberlake and Munn spent three days together at the Gansevoort Park Avenue hotel in New York City.
Jessica Biel 2011-Present
Justin and Jessica reportedly got back together over the summer of 2011. They were seen on vacation together and out and about with Biel’s parents. In December 2011, Timberlake popped the question to Biel.
On September 19, 2012, the two made it official in Italy.
Justin Timberlake and Jessica Biel started dating in 2007 and the couple sealed their bond of togetherness with marriage on October 19, 2012.
Justin Timberlake is happily married to Jessica Biel and they have been together for 11 years and still counting.