Justin Timberlake and Britney Spears were the hottest young couple of the late 90s, early 00s. The duo started dating in 1999, years after meeting on The Disney Channel’s The Mickey Mouse Club. Timberlake and Spears saw sparks while on tour together in 1998-1999.
Timberlake’s boyband, NSYNC, headed out on the multi-city, multi-leg “Second II None Tour,” which kicked off in November 1998. The group had various opening acts, including girl-group, B*Witched, Mandy Moore (who currently stars on This Is Us), and Britney Spears.
Spending time together on the road, Timberlake and Spears’ romance blossomed. They dated through 2002.
Here is what you need to know:
1. There Are Rumors That Spears Might Join Timberlake During His Super Bowl LII Halftime Performance
Ever since Justin Timberlake was announced as the headliner for the Super Bowl LII halftime show, many people have been wondering who — if anyone — Timberlake would include in his performance.
Upon hearing the news, Timberlake fans immediate wondered if he would invite his old pals from NSYNC to join him on the big stage, but NSYNC member Joey Fatone told TMZ that a reunion wasn’t happening — at least not on February 4.
Now, some people have turned their attention to the possibility of Spears making a guest appearance during Timberlake’s performance. That possibility isn’t too far out of the question either. For starters, Spears is indeed available; she wrapped her residency at Planet Hollywood in Las Vegas on New Year’s Eve and doesn’t head out on her summer tour until July.
Secondly, if this were to happen, it wouldn’t be the first time that Timberlake and Spears shared a Super Bowl halftime stage. In 2001, ‘NYSNC, Spears, and Nelly joined Aerosmith for an unforgettable rendition of “Walk This Way.” You can check it out in the video below.
2. A Collaboration Has Been Rumored for Years
A Timberlake-Spears collaboration has been rumored for years. Every time that there’s a new Timberlake or Spears album set to be released, the music world finds itself wondering if there’s going to be a track featuring the artists’s respective ex. Although the two didn’t split amicably (which you’ll read about in Fact 4), fans have long been waiting for it to happen — and have been given plenty of reasons to think that it might.
In 2016, for example, music mogul Timbaland was asked about Timberlake’s new album — specifically about “Justney,” the former couple’s relationship portmanteau. At first, Timbaland misunderstood the question he was being asked by the hosts of the Pop University podcast. However, they made it more clear and Timbaland responded, “Yes, it’s coming. It’s coming.”
Around the same time, Spears appeared on Most Requested Live With Romeo and received a fan question about which artists she’d like to work with in the future.
“Aerosmith [frontman Steven Tyler] seems really good and bright. He’s a genius, I think. He’s very rock ’n’ roll. He sings from his soul. Gwen Stefani, I think she’s great. Justin Timberlake is very good,” Spears responded. When E! News told Timberlake about Spears’ remark, he said that he was down to collaborate.
“She did? Sure! Absolutely, absolutely,” he said.
You can check out Spears’ “Ask Anything” segment below. She talks about collaborations around the 4:00 mark.
Timberlake’s latest album, Man of the Woods, was released on February 2. Of the 16 tracks on the album, only two are collaborations: “Morning Light” features Alicia Keys, while “Say Something” features Chris Stapleton. Alas, no collaboration with Spears.
When Timberlake and Spears were dating, they collaborated on one song, “What It’s Like to Be Me,” which is featured on Spears’ album “Britney.” You can listen to the song below.
3. They Met on the Mickey Mouse Club, Started Dating Several Months After They Met, & Broke Up in 2002
Timberlake and Spears met whilst working on The Mickey Mouse Club, a show that featured “comedy sketches, commercial parodies, music videos, celebrity guests, and a cast of talented young performers,” according to IMDb. Although the two didn’t date while filming the show (they were far too young to be in a relationship), they knew that they liked each other.
“We kind of kept in touch at the very beginning, but then after 3 months we stopped talking. And then we saw each other again. He was doing promotional stuff for NSYNC at a radio show, and he came backstage and I was there. He knocked on my door and then we saw each other, and ever since then we’ve been going out,” Spears told Frank Skinner back in 2002.
You can watch Spears’ interview with Skinner in the video below.
Both Spears and Timberlake spoke about their relationship as being “the one,” and both were completely heartbroken when things ended. They were asked about their relationship for years after their split, but both tried to keep things close to the vest.
In the interview below, Barbara Walters asked Timberlake about his breakup with Spears.
The following video shows Spears’ interview with Diane Sawyer in which she also is asked about her former relationship with Timberlake.
4. Many Believe That Spears Cheated on Timberlake With Wade Robson & Both She & Timberlake Have Released Songs Believed to Be About Their Split
Timberlake and Spears’ relationship ended in 2002. The going rumor is that Spears cheated on Timberlake with choreographer, Wade Robson, who has worked with both Timberlake and Spears on numerous occasions.
“Justin Timberlake uncovered Spears’ alleged affair with Wade Robson when he discovered a note in Spears’ room in February 2002, on the night that the two pop stars were scheduled to appear on Saturday Night Live,” Rolling Stone reported in 2010.
“The break-up was absolutely heartbreaking for me. I can’t just have meaningless relationships with women. I have to find Miss Right in order to have a relationship. There’s got to be that big moment when she comes along,” Timberlake told The Telegraph in September 2002.
Shortly after their split, Timberlake released the song, “Cry Me a River,” which is said to have been written in direct response to Spears’ alleged affair.
“In the past, suffering has helped me compose songs. ‘Cry Me a River’ was written in a time of pain, like everyone knows,” Timberlake told Vanity Fair Italia in 2016.
You can watch the music video for “Cry Me a River” below.
Spears released her own track, “Everytime,” believed to be an apology to Timberlake, the following year.
“I’m still hurting but I am trying to see it as an experience. The worst thing is everyone wants to talk to me about it. Everywhere I go people are asking how I am,” Spears reportedly told The Sun shortly after the split.
You can watch the “Everytime” music video below.
5. Timberlake Is Married to Jessica Biel & They Have 1 Son Together, While Spears Is Currently Dating Sam Asghari & Has 2 Sons From a Previous Relationship
Despite their fans hoping for some kind of rekindling, Timberlake and Spears never reconnected romantically.
Timberlake went on to date a few women in Hollywood, including Alyssa Milano (2002) and Cameron Diaz (2003-2006). In 2007, Timberlake met his now-wife, actress Jessica Biel. The two tied the knot at the Borgo Egnazia resort in the southern Italian city of Fasano in 2012.
Three years later, Timberlake and Biel welcomed their first child together, a son they named Silas.
Meanwhile, two years after her split from Timberlake, Spears married her childhood friend, Jason Alexander while in Las Vegas on New Year’s Eve. Fifty-five hours later, however, their marriage was annulled.
Months later, she started dating one of her back-up dancers, Kevin Federline. The couple had a whirlwind romance that was all documented on their short-lived reality series, Chaotic. The two married on October 6, 2004, and welcomed their first son, Sean Preston, the following year. A few months later, Spears got pregnant again. She gave birth to her second son, Jayden James on September 12, 2006. She and Federline split in 2007.
Since that time, Spears has dated a few guys including her manager, Jason Trawick, (to whom she was engaged), David Lucado and Charlie Ebersol.
She is currently dating model and fitness buff, Sam Asghari.