The below list is in no way exhaustive as there are far too many examples of Justin Timberlake being a complete troll, whether about Britney or just in general:
December 2000 - Justin Timberlake is sued for assault after allegedly pushing a 15-year old girl against a wall and verbally harassing her after she yelled “JC is cuter.”
September 2002 - In a Hot 97 Interview, Justin Timberlake talks about going down on Britney.
November 2002 - Justin Timberlake releases the Cry Me a River video, which infamously features a Britney lookalike. At the time, he insists that the song is not about Britney, claiming “The video is not about her. The video is about me,” but it’s confirmed that the video is intended to be about Britney by the video’s director years later. Justin Timberlake asks Britney’s permission before the video comes out, telling her “it’s not a big deal.”
December 2002 - In a Details magazine cover story, Justin Timberlake mocks Britney’s career choices, saying "If she had a clue, she wouldn't have made ['Crossroads']."
December 2003 - Justin Timberlake tells Rolling Stone that "what I did with Justified was ten times better than anything *NSYNC has ever done."
February 2004 - NIPPLEGATE: Justin Timberlake exposes Janet Jackson’s breast during the Super Bowl halftime show, which causes Janet to be blacklisted over the next decade, while Justin’s career flourishes, he suffers no career repercussions and he offers no public support for Janet until years later when he is about to perform at the Super Bowl again.
July 2006 - Four years after their breakup, Justin Timberlake whines to GQ Magazine that “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.”
January 2007 - Justin Timberlake mocks Prince (!) while accepting an award on his behalf at the Golden Globes
February 2007 - While accepting the Brit award for best international male solo artist, Justin Timberlake disses Britney in his acceptance speech: "Thank you very much for this. I’m very flattered. I’m actually on tour so I couldn’t be there. Everyone have a great night. Stop drinking! You know who you are. I’m speaking to you. You are going to get sloppy. OK! Magazine is going to say something bad about you.”
March 2008 - Justin Timberlake mocks Britney while inducting Madonna into the Rock and Roll Hall of Fame, saying “The world has always been full of Madonna wannabes, I might have even dated a couple.”
March 2009 - Justin Timberlake mocks Britney’s virginity in an SNL skit while playing a fictitious ancestor of his called Cornelius Timberlake, saying, “I’d like to think that at first, he’ll date a popular female singer. Publicly, they’ll claim to be virgins. But privately, he hit it.”
October 2012 - Justin Timberlake and Jessica Biel’s $65 million wedding (which the other members of *NSYNC are not invited to) includes a video shown at their reception which mocks LA street people.
October 2012 - Justin Timberlake jumps over Jessica Biel’s head in their People wedding cover.
October 2012 - Shriners Hospitals for Children parts ways with Justin Timberlake, with a representative from the charity saying, “We tried everything we could to get him more involved with our kids and the hospitals. But it seemed that when the TV cameras weren't on, he disappeared.”
February 2013 - Justin Timberlake calls Britney a bitch during a Super Bowl party performance, introducing the song Cry Me a River by saying, “Sometimes in life, you think you found the one. But then one day you find out, that she is just some bitch!”
May 2013 - While promoting his film Inside Llewyn Davis, Justin Timberlake whines about how his “music career hangs over me like a cloud.”
July 2013 - Justin Timberlake releases a song called “Take Back the Night” then claims he had no idea that it was the name of a foundation dedicated to ending domestic and sexual violence.
November 2013 - Justin Timberlake is named Man of the Year by GQ and spends the entire interview whining, including telling the interviewer “you sound like a dickhead,” saying that he feels “literally like a bunch of people just took a shit on my face,” has an outburst about reviews saying “you're trade magazines. None of your opinions count. And by the way, none of you can do it.” and moans about how “sometimes I just want to f–king kill everybody.”
August 2016 - When VF Italia asks Justin Timberlake if he needed to be "depressed or tormented" in order to write a good song, he brings up Cry Me a River, (14 years after its release) saying “Depends. In the past, suffering has helped me compose songs. ‘Cry Me a River’ was written in a time of pain, like everyone knows…”
February 2017 - Justin Timberlake tells The Hollywood Reporter that, in regards to *NSYNC, he “cared more about the music than some of the other people in the group.”
January 2018 - Justin Timberlake disses Vegas residencies during an interview with Beats One Radio saying “I mean I wouldn't rule it out if it was something that was different. I definitely don't … you know … [laughs] … it feels like … you're planning your retirement. You know what I mean? So for some reason that feels like scary to me.”
October 2018 - Justin Timberlake uses Britney to promote his new book, (16 years after their breakup) saying “I’ve been scorned. I’ve been pissed off. I wrote ‘Cry Me a River’ in two hours. I didn’t plan on writing it. The feelings I had were so strong that I had to write it, and I translated my feelings into a form where people could listen and, hopefully, relate to it. People heard me and they understood it because we’ve all been there.”
Here are some items we didn’t get a chance to cover because there’s just too many examples of Justin’s douchery through the years:
Justin Timberlake bragged to members of their tour about having sex with Britney.
Justin Timberlake wanted to fight Dax Shepard after his infamous Punk’d episode.
Justin Timberlake was accused of spitting on Swedish teenage fans in 2007.
Justin Timberlake has some sort of one-sided feud with Ryan Gosling (examples of their awkwardness at the 2017 Oscars here).
Justin Timberlake caused a scene about being photographed at Rihanna’s NY Fashion Week party in 2015.
In 2016, Justin Timberlake faced major backlash on Twitter after tweeting about Jesse Williams’ BET Awards speech, patronized those tweeting at him, and then got defensive when people called him out on being patronizing.
During a Songwriters Roundtable hosted by The Hollywood Reporter, Justin Timberlake tried to claim that he did the Trolls movie to empower women and then interrupted Tori Amos.
Justin Timberlake claimed after the fact that he wrote the song Can’t Stop the Feeling to be about “inclusion.”
Justin Timberlake served people grasshoppers and ants at the Man of the Woods album launch to demonstrate his woodsmanliness.
Justin Timberlake used Asian people as props in his Filthy video.
Justin Timberlake claimed to support sexual assault survivors while working with Woody Allen.
In 2018, Justin Timberlake faced backlash for holding a listening party for his Man of the Woods album at Paisley Park, Prince’s home (the man he mocked and ‘feuded’ with).
Also in 2018, he made *NSYNC’s Hollywood Walk of Fame ceremony all about him.
As we mentioned, Elaine Lui over at LaineyGossip has been at the forefront of trying to expose Justin Timberlake for what he is for more than a decade now. Here’s a link to the Justin Timberlake tag on the site for you to peruse the full archive of her sounding the alarm on him.
Here is more about Justin’s longstanding pattern of cultural appropriation:
Here is the We Need to Talk About Britney podcast episode with Lance Bass mentioned in this episode. Here also is the documentary, The Boy Band Con: The Lou Pearlman Story, that Lance executive produced.
And at this point, we just can’t stop linking to things about why Justin Timberlake is the worst, so here’s some more:
Thanks for listening!