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All the Controversy Surrounding Justin Timberlake, From His Recent Arrest to Rumoured Scandals

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Pop idol, *NSync alumnus, 10-time Grammy award winner, sports bar owner, movie star, and celebrated musician — By all accounts, the career of Justin Timberlake is worthy of admiration, if you ignore all the red flags and controversy that has haunted his footsteps over the years. In light of his recent arrest for driving under the influence, we look back at the controversial events that have cemented his place in pop culture as a dramatic king who is most certainly crying himself a river right now. 

Jessica Biel is a saint. 

Call it loyalty, pride, or simply love — having suffered the indignities of cheating scandals from her husband, Biel has reacted with incredible grace, trusting her silence to speak for itself. The internet, however, holds no such affection for Timberlake, whose recent run-in with the law has sparked many a Twitter thread (now X). From hilarious comments to now iconic memes, the internet has reacted as it often does: With derision, disgust, and much humour, sans all the delicacy that Biel has shown. 

Having erupted on social media for his recent arrest on June 18 for driving under the iNFLuence, Justin Timberlake has once again put himself in the spotlight with fresh controversy. In a startling reminder that what goes around truly does come around, JT’s recent arrest comes on the heels of Britney Spears’ tell all biography, The Woman In Me, which provided a damning glimpse into the then-teenage couple’s tumultuous relationship. 

Back in the day, it had been easy for onlookers and bystanders to dismiss Spears as the reason it all came crashing down. However, recent revelations from her book have shown us that Timberlake may not have been as blameless as he would have liked the world to believe. 

In honour of Spears’ courage in speaking out, Let’s Take A Ride back into memory lane and recount all the controversial moments in Justin Timberlake’s career. And no, we will not be getting into a car with him. 

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A timeline of every controversy that Justin Timberlake has been involved in 

His relationship with Britney Spears 

Ask any millennial who was deeply entrenched in pop culture in the 1990s, and they’ll tell you that The royal couple of the time was Britney Spears and Justin Timberlake. Both Mouseketeers who kicked off their now-iconic careers with Disney, the couple first met in 1992 when they were cast in The All-New Mickey Mouse Club alongside Ryan Gosling, Christina Aguilera, Keri Russell, and JC Chasez (also of *NSync).

Speaking to GQ in 2006, Timberlake shared that he was head over heels for Spears from the get-go, saying, “I was in love with her from the start.” 

justin timberlake controversy arrest
Controversy king Justin Timberlake picture with Britney Spears at the 2001 American Music Awards, a year before he reportedly broke up with her over a text message. (Image: @allurequinn/X (formerly Twitter)

The couple went public with their relationship seven years later in 1999, when Timberlake was 18 and Spears was just 17 years old. Riding high on the media attention and the intoxicating blooms of first love, they proceeded to make a myriad of public appearances together, including at the Super Bowl XXXV in 2001, where they performed at the half time show alongside *NSync, Aerosmith, Nelly, and Mary J. Blige. By all accounts, the couples’ relationship was the royal wedding equivalent of the ’90s, with fans hungrily following their every move in anticipation of the fairytale ‘happily ever after’. 

Reality, however, was much less happy, and much more fraught with controversy, Scandal, and tragedy. 

By the time the couple split in early 2002, reports had begun to emerge of Spears’ infidelity during the relationship. The public and media were quick to condemn Spears for her actions, with many taking the side of America’s Golden Boy, who allegedly ended the relationship via text message (we’re looking at you, Joe Jonas). For his part, Timberlake appeared to affirm the notion that he was the wronged party in the relationship, appealing to the public for understanding and in the same breath performing a song called Horrible Woman which appeared to take shots at Spears. That same year, he released Cry Me A River along with a controversial music video that featured a Spears lookalike performing unfaithful acts while in the confines of a relationship. 

Appearing to clap back, Spears released Everytime in 2003, a song widely regarded to have been about her relationship with Timberlake. While the song became a hit, it did little to gain forgiveness in the public eye, with Diane Sawyer asking her in an interview that same year, “You did something that caused him so much pain… so much suffering. What did you do?”

Diane Sawyer, we hope you’re having the day you deserve.

Battling her personal demons from mental Health issues to her highly criminal conservatorship, Spears remained mum on the truth until the release of her tell-all memoir The Woman In Me in 2023. In the biography, Spears provided deeper insight into her relationship with Timberlake. Admitting that she had cheated once by kissing a backup dancer, she went on to add that “there were a couple of times during our relationship when I knew Justin had cheated on me.” 

However, the biggest bombshell to emerge from the book was the revelation that Spears had become pregnant with Timberlake’s baby — a pregnancy he was markedly unhappy about. According to Spears, she underwent an abortion at Timberlake’s urging, sharing that he had said they were not ready for a baby, and that they were too young. Spears has since shared that while she agreed to abort the baby, she also does not know if that was the right decision. 

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A post shared by PS (@ps.feelgood)

Following the furore and fallout of her memoir, Spears publicly apologised to Timberlake. While the appropriate and classy response for burying the decades-old hatchet would have been for Timberlake to do the same, Mr. SexyBack said ‘it’s not gonna be me’ and declared during a one-night show in New York City that he wanted to apologise to “absolutely f–cking nobody.” 

Alexa, play It Takes Two by Justin Timberlake. 

Nipplegate 

In 2004, while performing a duet at the halftime show of the Super Bowl XXXVIII alongside Timberlake, popstar Janet Jackson suffered the discomfort of a very public wardrobe malfunction. And while we know there were other forces at play, we are Petty and want it on record that yes — it was all JT’s fault. The mishap occurred while Timberlake and Jackson were performing Rock Your Body, which featured the oddly prophetic lyrics, “Bet I’ll have you naked by the end of this song.” 

To the surprise of 140 million viewers, Timberlake delivered on his promise, reaching forward to pull off a part of Jackson’s outfit to reveal her right breast. The event rightly went viral, after which Timberlake spoke up to address the wardrobe malfunction, adding that it was unintentional and regrettable. 

It bears noting that while Justin ‘Can’t Stop The Feeling’ Timberlake escaped the incident with his career and reputation largely intact, Jackson was met with much public outcry. Speaking out during her 2022 television documentary Janet, Jackson shared that she had encouraged Timberlake to remain silent in the hopes that the drama would elude him, adding that “They’re aiming all of this at me.” She went on to say that the entire incident had been blown out of proportion, adding, “Of course, it was an accident that should not have happened, but everyone is looking for someone to blame and that’s got to stop,” 

Timberlake eventually apologised to both Jackson and Spears in 2021. In a now-deleted Instagram post, he expressed contrition for ‘contributing to the problem and benefitting from a system that condones misogyny and racism’. By Jackson’s own admission, the two remain friends to this day. 

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Cheating allegations 

Timberlake first met his future wife actress Jessica Biel in 2007. However, a rift would emerge between the couple in 2010, when he was reported to have had a ‘three-day fling’ with actress Olivia Munn, whom he met in a MySpace Live Chat event as part of promotions for The Social Network.  

According to US Weekly, Timberlake had told Munn that things were over between him and Biel, and the duo suMMArily engaged in their now-infamous tryst. According to sources, Munn eventually figured out that she was being taken for a ride and called the whole thing off. Timberlake’s representatives vehemently denied the allegations; however, he and Biel then ‘took a few months off’ from one another before eventually rekindling their romance. A year later, they tied the knot. 

Cheating allegations, part two 

In 2019, Justin Timberlake once again came under media fire when he was photographed in New Orleans, holding hands with his Palmer co-star Alisha Wainwright. According to reports, the inebriated Timberlake “appeared to have been drinking heavily” and was “unsteady on his feet”. He also did not appear to be wearing his wedding ring. 

A public apology followed soon after, with Timberlake expressing his sincerest regret for the incident. “I stay away from gossip as much as I can, but for my family I feel it is important to address recent rumours that are hurting the people I love. A few weeks ago I displayed a strong lapse in judgment – but let me be clear – nothing happened between me and my co-star,” he shared on a social media post. 

Pointing to a careless overindulgence in drink, Timberlake conveyed that he should have known better, citing a desire to set a good example for his son and adding, “I apologise to my amazing wife and family for putting them through such an embarrassing situation, and I am focused on being the best husband and father I can be. This was not that.” 

Recent DUI arrest of Justin Timberlake marks a fresh controversy

Last week on the morning of June 17, Justin Timberlake was arrested on DWI (Driving While Intoxicated) charges. The incident occurred in the Hamptons, where the star had been partying with friends at the American Hotel. According to reports, Timberlake was pulled over by the authorities after he ran a stop sign and began swerving unsteadily on the road around 12:15 AM. He was driving a 2025 Grey BMW. 

Allegedly glassy-eyed and smelling of alcohol, Timberlake told officers that he had only had ‘one martini’; however, it was also reported that he failed a field sobriety test and refused a breathalyser, saying, “This is going to ruin the tour.” The singer has been on the road since April for his Forget Tomorrow World Tour. 

In an almost karmic turn of events, the cop, who appeared too young to recognise Timberlake simply responded, “What tour?” 

Timberlake appeared in court on June 18 and was released without bail. Because he has no prior criminal record, it is expected that he will receive a USD 500 fine and a 90-day suspension of his driver’s license in New York. 

Online reactions to Timberlake’s arrest have ranged from amusement to delight. Across the board, denizens of the internet have taken to heckling the star for his misfortunes and scandals. One Instagram commenter known as @blameleestewart said, “What goes around (goes around goes around goes around) comes around.”

Another commenter on the same post @omr.mendoza said, “Justin: When am I getting out? Judge: It’s gonna be mayyy.” 

Timberlake is due back in court on July 26; however, he is not required to attend in person. 

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(Main and featured image: Amy Sussman/ Getty Images North America/ Getty Images via AFP)

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