Every Time Justin Timberlake Seemingly Shaded Britney Spears After Their 2002 Split

“He’s talking about her letting the past go, but he’s been the one bringing it back up over the years just to humiliate her,” one person commented.

Britney Spears and Justin Timberlake were 12 years old when they first met after being cast in Disney’s Mickey Mouse Club reboot back in 1993.

Britney and Justin on "The Mickey Mouse Club"

Each star has been open about having a crush on the other during this time, but when Justin left the show the following year, their love story was cut short.

Closeup of Britney and Justin as kids

The pair reconnected in the late ‘90s, and officially started dating in 1999 until their bitter split in 2002.

Closeup of Justin and Britney sitting at an event with Lenny Kravitz behind him

In recent years, Justin has faced fierce backlash for the way that he treated Britney after their breakup, with Britney being heavily vilified in the media at the time after he fueled speculation that she had cheated on him.

Closeup of Britney

Most famously, this included a Britney lookalike being cast in the music video for Justin’s second solo single, “Cry Me a River,” which is about finding out that your partner has been unfaithful.

Screenshot from the "Cry Me a River" video

And Justin’s behavior has faced fresh scrutiny this month ahead of the release of Britney’s memoir, The Woman in Me. Preview excerpts have included some shocking revelations about their relationship, including Britney’s claim that Justin had actually cheated on her “a couple of times” when they were together.

Closeup of Britney and Justin

She also reveals that she had an abortion because Justin “didn’t want to be a father.” Per People, Britney says that the abortion remains “one of the most agonizing things” that she has ever experienced, and that if it’d been left up to her alone, she never would have gone through with it.

Closeup of Justin and Britney

Justin is said to have played guitar while Britney was left “crying and sobbing” on the bathroom floor after the procedure.

Closeup of Britney and Justin

While Justin has not publicly responded to any of these reports, a source told Entertainment Tonight last week that he is “focusing on his own family and trying not to concern himself with Britney’s memoir.”

Closeup of Justin Timberlake

They added: “In recent years, Justin has tried to be supportive of Britney from a distance. They dated so long ago, but he still has respect for her. Justin and Jessica [Biel, Justin’s wife] just want everyone to grow and evolve instead of continuing to bring up the past."

Closeup of Jessica Biel and Justin Timberlake

But this remark has rubbed some people the wrong way, with many taking to social media to point out that Justin would regularly bring up the past after his and Britney’s split.

Closeup of Justin Timberlake

And a compilation of just some of these moments has recently gained traction on TikTok, with the video’s creator saying in the caption: “He's been bringing up the past for the last 20 years nonstop, exploiting a young woman whom he forced to get an abortion, mocking her in every chance he got.”

Closeup of Justin Timberlake

But the examples shown in the video are just the tip of the iceberg, with Justin’s apparent digs at Britney spanning from 2002 until 2018.

Closeup of Justin

Justin first began to make crude comments about his and Britney’s sex life in November 2002, just months after their split.

Closeup of Justin

This was of particular interest to people at the time because Britney had said as a teenager that she didn’t plan to have sex before marriage.

Closeup of Britney

During a sit-down interview with Barbara Walters, Justin was asked if Britney had lived up to this past promise. He smirked and made no secret of his sarcasm as he said: “Sure,” making it clear that this wasn’t the case.

Justin being interviewed

Elsewhere in this interview, Justin fueled the belief that his famous ex had wronged him, and even played Barbara his previously unheard song “Don't Go (Horrible Woman),” which was heavily implied to be about Britney.

Justin playing piano for Barbara Walters

The lyrics once again paint Justin as a victim and include the line: “At least you gave me another song about a horrible woman.”

Lyrics to Justin's song

That same month, Justin was bluntly asked: “Did you fuck Britney Spears?” during an appearance on Hot 97. The star was all-too-keen to play up the discourse as he gleefully shouted: “OK, I did it!”

Closeup of Justin Timberlake

The hosts went on to question whether he and Britney had had “oral intercourse,” and Justin laughed as he replied: “I did it, I’m dirty!”

Closeup of Justin

The following year, Justin appeared on stage with Christina Aguilera as she hosted the MTV EMAs. This was already pretty pointed, as Britney and Christina had been portrayed as music rivals in the media ever since their respective careers took off.

Closeup of Justin and Christina

But Justin went one step further with a gag that appeared to once again sexualize and degrade his famous ex. In the skit, Christina tells Justin that he “left a couple things on the tour bus” before a blonde sex doll was brought onto the stage.

Justin and Christina onstage

Justin plays along as he says he’d been “looking for that everywhere,” and laughs as Christina makes an obvious jibe at Britney by stating that people thought “it looked kind of familiar to somebody.”

Justin and Christina onstage

By 2007, it was evident to all that Britney was struggling with her mental health as she was pictured shaving her head shortly after leaving a rehab facility. Justin won a Brit Award during the height of her breakdown, and was accused of making reference to her partying during his acceptance speech.

Closeup of Britney

Speaking directly into the camera, Justin said at the time: “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.”

Closeup of Justin holding an award

When confronted by GQ magazine over whether this had been a coded message to Britney, Justin denied it. However, the accompanying photoshoot for this interview included a picture of Justin shaving his head, which was not lost on readers.

Closeup of Justin

The singer was also accused of taking jabs at Britney during his 2007 tour, where he would perform mashups of his song “Cry Me a River.” The songs “Rehab” by Amy Winehouse and “Crazy” by Gnarls Barkley were two of these mashups, with Justin also choosing to change some of the lyrics.

Justin onstage

While videos of these performances have since been scrubbed from the internet, it has been reported that Justin changed the “me” and “I” pronouns to “she” and “her.” For example, instead of singing: “They tried to make me go to rehab,” Justin is said to have sung: “They tried to make her go to rehab.”

Lyrics to "Rehab" by Amy Winehouse

And instead of “I remember when I lost my mind” and “I think you’re crazy” in “Crazy,” Justin apparently sang: “I remember when she lost her mind” and “I think she’s crazy.”

Lyrics to "Crazy" by Gnarls Barkley

In addition, amid the breakdown of Britney’s marriage to Kevin Federline, Justin released his song “What Goes Around… Comes Around.” The song is about infidelity in a relationship and karma, and the public quickly began to speculate that it was about his ex.

Closeup of Kevin Federline and Britney Spears

Meanwhile, the recent TikTok starts with a troubling moment from 2008, six years after Justin and Britney’s split. In the first clip, Justin is introducing Madonna as she gets inducted into the Rock and Roll Hall of Fame, and he couldn’t resist making an obvious dig at Britney during his speech.

Justin onstage

“The world has long been full of Madonna wannabes, and I might have even dated a couple,” he smirks, to the cheers and whoops of the audience.

@calabasaswings

he's been bringing up the past for the last 20 years non-stop, exploiting a young woman whom he forced to get an abortion, mocking her in every chance he got. Talentless Jessica Biel shade to brit's lingerie line in 2014 for no reason. now they're talking about growing? Hilarious #justintimberlake #shade #britneyspears #justiceforbritney #thewomaninme

? original sound - Stefano
TikTok @calabasaswings / NBC / Via tiktok.com

The following year, Justin once again rehashes his anecdote about Britney’s vow to not have sex before marriage during an appearance on Saturday Night Live.

Justin on "SNL"

In a skit, Justin quips: “I'd like to think that at first, popular female singers publicly will claim to be virgins, but privately he hit it."

Closeup of Justin

During another skit on the same episode, Justin sings Britney’s hit 2001 song “I’m a Slave 4 U” while dressed in a banana costume, and seemingly pokes fun at her sexy dance moves from the music video.

Justin on "SNL"

Fast-forward to 2013, now over a decade since his and Britney’s split, and Justin alluded to her at a Super Bowl afterparty. Before playing “Cry Me a River” during his set, Justin told the crowd: “Sometimes in life you think you found the one, but then one day you find out that she is just some bitch.”

Closeup of Justin

And in 2018, just five years ago, Justin was accused of taking yet another swipe at Britney when he was asked if he would ever consider a residency in Las Vegas. At this point, Britney had been performing a hugely successful and in-demand Vegas show for five years — but Justin scoffed at the suggestion.

Britney onstage

Implying that Vegas residencies were something singers resorted to only after their careers had faded, Justin said that having one would feel like "planning your retirement."

Closeup of Justin

And fans had a lot of thoughts about Justin’s repeated digs at Britney in the TikTok’s comment section, with many pointing out the double standards amid the source quotes released in response to Britney's memoir.

Closeup of Justin

One person wrote: “He’s talking about her letting the past go, but he’s been the one bringing it back up over the years just to humiliate her.”

“He’s talking about her letting the past go, but he’s been the one bringing it back up over the years just to humiliate her.”

“In the end he is asking that he not be judged for his past with her when he spent years making money at the expense of what he lived with her,” another said.

“In the end he is asking that he not be judged for his past with her when he spent years making money at the expense of what he lived with her."

One more commented: “Honestly, Britney Spears was probably the most interesting thing about his life… so that’s really a flex on her. ? ?”

“Honestly, Britney Spears was probably the most interesting thing about his life… so that’s really a flex on her. ? ?”

Another user echoed: “I never followed him because I never liked him. Had no idea he was so obsessed with Britney Spears. ?”

“I never followed him because I never liked him. Had no idea he was so obsessed with Britney Spears. ?”

“This is so wrong, I can't believe how he humiliated Britney,” someone else wrote. Another simply added: “I am so disappointed… ?”

“This is so wrong, I can't believe how he humiliated Brittney"
"I am so disappointed..."

Britney has barely acknowledged any of Justin’s swipes over the years, but in March of last year, she did accuse him of using her name for “fame and attention” in an Instagram post that she later deleted.

Closeup of Justin Timberlake

Meanwhile, Justin issued a public apology for his past behavior after it was called out in the New York Times’ 2021 documentary Framing Britney Spears.

Closeup of Justin

Responding to increasing scrutiny in an Instagram statement at the time, Justin admitted that he had “benefited from a system that condones misogyny.”

Britney’s memoir will be officially released on Tuesday, so it’s safe to assume that there are plenty more revelations ahead.

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