From the moment that he broke up with Britney, she went from being his ex to being the key to his successful solo career. Every chance he got, he played the broken-hearted victim while Britney (who tried to make amends) was publicly dragged and demonized for “betraying” him. Luckily for Justin, countless tabloids continued to take his side and brainwash fans into believing this narrative. It gave him the perfect opportunity to milk that messy breakup for all it was worth and, as a result, his career continued to skyrocket.
Although we respect the former *NSYNC boybanders talent, it irks us that he felt the need to capitalize off of Britney’s pain to become more successful. And to make matters even worse, he publicly insulted Britney on several occasions – all of which were completely uncalled for. See all the times Justin totally disrespected or embarrassed the pop star:
18. He was spotted with another girl while he was still dating Britney.
In 2000, Justin was seen hanging out with Nicole Appleton from All Saints, and immediately word of infidelity on Justin‘s part began to circulate. Both JT and Nicole tried to hide their faces from the paparazzi as they headed from a London nightclub to Justin’s hotel. At the time, Nicole had recently split with her ex-fiance, Robbie Williams. Of course, it was Britney who got slammed for allegedly cheating on Justin publicly.
17. He told his former choreographer to smell his fingers after he slept with Britney.
Although Justin and Britney convinced everyone that they planned to be abstinent before marriage, the two secretly hooked up one night. And after it happened, Justin actually told his former choreographer, Darrin Henson, to smell his fingers – so says Darrin at least. The choreographer recalled: “They were always running in between each other’s buses, and one night Justin came back to the bus and said to me, ‘Dude, smell my fingers.’ Justin slept with her that night.” Gentlemen don’t kiss and tell, Justin! Talk about gross.
16. When he found out that Britney allegedly cheated, he went solo and released a diss track about her.
The name of that track was “Like I Love You.” And if it’s not ringing a bell, that’s because the song didn’t do so well, peaking only at number 11 on the charts. Justin initially denied that the song was about Britney, but fans weren’t fooled because the lyrics seem to prove otherwise.
There was also the fact that he failed to step up and come to Britney’s defense when the song sparked rumors about the breakup. Everyone started painting her as the betrayer… And he played along.
15. He did a Barbara Walters interview and painted himself as the victim.
He claimed that he wouldn’t go into detail about why they broke up… And then proceeded to do the exact opposite of that. He stated that none of his songs were inspired by his relationship with Britney, but then he went on to sing the following lyrics from “Horrible Woman” for Barbara: “I thought our love was so strong, I guess I was dead wrong, But to look at it positively, hey girl, At least you gave me another song about a horrible woman.” Interesting choice, don’t you think?
14. …And he spilled the beans about taking Britney’s virginity.
Well, he didn’t come right out and say it. But he made it quite clear from the way he responded to a question from Barabra Walters that they did have sex for the first time together. When she asked him if Britney honored her promise to stay a virgin until marriage, he replied “sure” and then started laughing. …Like, how immature can you be?
13. Since there was so much buzz about his recent breakup, he went on to release another diss track.
And that was the infamous “Cry Me A River,” which gained a lot more success than the first. Keep in mind that he found out from a friend that Britney was cheating on him. Only hours before he and Britney were set to perform on SNL, Justin found a “mash note” written by Wade Robson in Britney’s dressing room and immediately broke things off. Now, check out the song’s lyrics: “You don’t have to say what you did, I already know, I found out from him. Now there’s just no chance with you and me. There’ll never be. Don’t it make you sad about it?”
12. Justin tricked her into approving of a Britney look-alike for the music video.
The story goes that Justin called Britney before filming the “Cry Me a River” music video and pretended that he just wanted to catch up as friends. But then, he casually slipped in the fact that he planned to use her look-alike in his music video for the song. She couldn’t think fast enough to object to the idea, and so when she finally saw it, she was apparently shocked to see a sort of “recreation” of their breakup. Using a look-alike in your breakup music video is kind of shady in the first place, anyways.
(Though we totally approved of it when Rihanna used a Chris Brown look-alike in the “We Found Love” video, TBH.)
11. During an interview to promote his album, he shaded Britney.
When he appeared on The Ellen Show, Ellen brought up the notorious music video and asked Justin who it was about. (Classic Ellen DeGeneras getting right to it!) She even said that the lady in the video looked familiar. The audience laughed out loud and, instead of giving a straight answer, Justin sipped his tea with raised eyebrows like a legit drama queen. He may as well have said: “Yes, of course, it’s about Britney.”
10. The press ate it up like candy and took Justin’s side, making Britney look like the villain.
The saddest part is that Justin was more than happy to go along with the rumors about Britney because it was really good for his image. Countless magazine covers featured Britney with headlines claiming she either betrayed Justin or single-handedly destroyed the relationship. Meanwhile, Justin was the “hero.” Or rather, the innocent victim struggling to overcome his recent heartbreak.
9. He dissed Britney’s movie, Crossroads
In an interview with Details magazine, Justin randomly criticized Britney’s decision to take on an acting gig. He said: “If she had a clue, she wouldn’t have made [Crossroads].” …Yeah, of course, Justin. Because you’re the expert on what works best for Britney’s career. Obviously.
8. He talked more about their sex life during a live interview.
During his interview with Hot 97, he was asked if he had “oral intercourse” with Britney. He could have easily declined to answer, but no. He actually admitted that he went down on Britney, saying: “I did it. I’m dirty.” Jeez… Talk about cruel. Publicly talking about the sexual choices you and another person make in private is basically the definition of douchey. Just ask John Mayer, right?
7. 4 years after their split, he brought up Britney again in a. interview.
At the time, Justin Timberlake was dating Cameron Diaz and promoting his new album, FutureSex/LoveSounds. And yet, he still found a way to bring up a breakup that happened over four years before. He said: “I felt like she had a couple of opportunities to just sort of stick up for me, and she didn’t. Which is ﬁne. But at that time, you know, I fought back, and that’s the way I fought back. I used my mind. I came up with a song.” … Get over it, dude! Also, you want to talk about people not sticking up for their exes? PUH-LEASE.
6. Then he released yet another diss track…
In 2006, Britney was struggling with anxiety and going through a very public mental breakdown. So of course, Justin thought it would be fitting to release what critics would call a “sequel” to his earlier hit, “Cry Me A River.” From his album FutureSex/LoveSounds, he released a single about betrayal called “What Goes Around… Comes Around.” You may remember it considering it’s an absolute banger, but his intentions were certainly bad for making this song. He didn’t use a look-alike for the music video, but it’s quite obvious that the song was just his classic way of saying “Karma’s a b*tch, Britney.”
5. He called Britney a “Madonna wannabe.”
While inducting Madonna into the Rock and Roll Hall of Fame in 2008, he called Britney a “Madonna wannabe.” In the middle of listing her achievements, he mentioned Britney and Madonna’s infamous kiss from 2003, and he said: “The world has long been full of Madonna-wannabes, and I might have even dated a couple. But there is truly only one Madonna.” …Ugh. WHY WHY WHY?!
4. 7 years after their split, he went on SNL and talked about his and Britney’s sex life.
In 2009, he appeared on Saturday Night Live and did a brief skit about immigrants. During the sketch, he referenced the lie about Britney saving herself for marriage AGAIN. Pretending to be one of his distant ancestors, he said of his great, great, grandson (AKA Justin Timberlake): “I’d like to think that, at first, he’ll diss a popular female singer. Publicly, they’ll claim to be virgins but privately… he hit it.”
And to make sure that people didn’t miss the reference, he continued: “Then, he’ll make love with women so beautiful and so often that it won’t be enough for him and he’ll, I don’t know, try some stuff with guys. I mean, he’ll be straight! Forget that part! Everything is true except that part!”
3. He seemingly called Britney a bitch in one of his live performances.
Just before performing “Cry Me A River” at one of his live events in 2013, Justin said: ”Sometimes in life, you think you found the one. But then one day you find out that she was just a bitch.” He later went on Twitter and of course, denied that the quote was a reference to Britney. The was OVER a decade since they’d broken up. What is wrong with this guy?!
2. Justin & Timbaland got majorly butthurt when she refused to work with them.
The duo wanted to join forces with Miss Spears when she was back in the rise after her mid-aughts breakdown. According to Timbaland, he and Justin Timberlake would’ve “helped her out a whole lot” and been “the best thing that ever happened” (as if she needed her immature, opportunist ex and his producer to be successful?). But Britney, knowing their end-game, dissed them both by turning down the offer.
In an interview, Timbaland mentioned that she should “humble herself” and “apologize” for kicking them to the curb. He said: “She has no comeback story. That’s the problem. She has to have a team. She needs to come back with Justin doing records; [then we’d see headlines like,] ‘She went back to her ex and she’s making smashes.’ [But instead, she got] so big-headed and [was] like, ‘Screw you, screw you, I don’t need nobody.'” Well, that’s kind of the point, Timbaland. She actually had an epic comeback and she didn’t need to return to Justin to do it.
1. Over 14 years after their split, he mentioned their breakup in an interview with Vanity Fair.
He never mentioned her name, but he didn’t have to. When he was asked if he needed to be “depressed or tormented” to create a really good song, he used that opportunity to bring up “Cry Me a River.” He said: “Depends. In the past, suffering has helped me compose songs. ‘Cry Me a River’ was written in a time of pain like everyone knows.” …Well, how could everyone not know, considering that you keep bringing it up, Justin??