justin timberlake arrest
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How Justin Timberlake Went From Hollywood Idol to Cringeworthy Has-Been

The singer's DWI arrest is only his latest misstep.

Justin Timberlake has been a boy band heartthrob, one half of an iconic celebrity coupling, film scene-stealer and now… maybe a has-been? On June 18, it was revealed that the singer had been arrested in the Hamptons for driving while impaired (DWI). Soon after the news was released, Timberlake’s mugshot started making the rounds. The internet reacted to the Justin Timberlake arrest as you would expect strangers on social media to in 2024: swiftly and with no punches pulled.


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In the wake of his arrest, the general sentiment about JT has remained pretty consistent online: Timberlake is no longer a heartthrob, but a certified knob. It’s safe to say that the former NSYNC singer’s status as an idol has officially ended — and there’s a pretty specific reason why.

Justin Timberlake’s arrest sent the internet into a tizzy

There aren’t many things, aside from rumours of cannibalism that could officially cancel a seasoned Hollywood career, and although a Timberlake DWI, while obviously very serious, might have not phased fans even a decade ago, at 43-years-old, the arrest felt different.

Almost immediately after the news broke, the internet went wild, with social media users sharing memes of Timberlake in handcuffs and tweeting gleeful photos of Janet Jackson above the news (IYKYK). While some people did show some sympathy for the singer’s situation, most feelings of goodwill were directed towards his wife Jessica Biel. (The same day Timberlake was arrested, Biel was photographed on set of her new TV series The Better Sister).


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This is far from the first time Timberlake hasn’t been a fan fave

The reaction towards Timberlake makes sense given the fact that this is far from the first time the singer’s reputation has been in major hot water, starting all the way back in the early 2000s with the now-infamous Super Bowl XXXVIII halftime show controversy, otherwise known as “Nipplegate.” Ugh.

In February 2004, Janet Jackson and a newly solo Timberlake performed together at the Super Bowl halftime show. During the performance, while the duo were crooning to Timberlake’s “Rock Your Body,” a wardrobe malfunction caused Timberlake to rip off part of Jackson’s top, revealing not the red bustier underneath, but the singer’s bare breast. In the aftermath, Janet was unfairly blamed for the mishap, with the incident causing her to lose out on business opportunities, including being cut from the Grammys that year.

Meanwhile, Timberlake emerged from the incident relatively unscathed, receiving critiques for seemingly abandoning Jackson in the aftermath but ultimately not suffering major career or business opportunities. His unwillingness to publicly speak out and support Jackson was especially notable given the fact that Timberlake has consistently built his career on appropriating Black culture when it suited him (see: his ill-gotten Man of the Woods era).

Over a decade later, Timberlake was once again back in the press in December 2019 when he was photographed at a bar in New Orleans getting *extremely* cozy with his Palmer co-star Alisha Wainwright. In photos at the time, the pair were pictured holding hands, with Wainwright’s hand on the singer’s knee. A few weeks after the incident, Timberlake took to Instagram to issue a since deleted apology, writing: “A few weeks ago, I displayed a strong lapse of judgment — but let me be clear — nothing happened between me and my costar. I drank way too much that night and I regret my behavior. I should have known better. This is not the example I want to set for my son [Silas].”

And then came the Britney Spears memoir. In her 2023 book, The Woman in Me, Spears — who dated Timberlake from 1999 to 2002 — made several allegations about the singer that cast him in an unfavourable light. Spears’ allegations included that Timberlake encouraged her to have an abortion during their relationship, and cheated on her a “couple” of times. In addition to this, in the wake of their 2002 breakup, Timberlake seemingly used the media to pit the public against his ex, releasing the 2003 music video for “Cry Me a River” starring a Spears lookalike, heavily implying that she had cheated on him. This led to vitriol and sex-shaming aimed at the “Lucky” singer.

All around, it wasn’t a good look. And it seems like Timberlake finally realized that. In 2021, the singer responded to convos around his treatment of women in his life during Spears’ highly-publicized conservatorship battle. In another since-deleted statement posted to his Instagram, Timberlake apologized for “missteps” he says contributed to a “system that condones misogyny and racism,” writing: “I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn, or did not speak up for what was right.”

Speaking to Spears and Jackson directly, Timberlake continued: “I specifically want to apologize to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed. I also feel compelled to respond, in part, because everyone involved deserves better and most importantly, because this is a larger conversation that I wholeheartedly want to be a part of and grow from.”

But Timberlake’s career may not make it out of this scandal — for a very important reason

Which brings us to Timberlake’s June 2024 DWI. Unlike his former indiscretions, fans weren’t so quick to forgive, instead using the opportunity to share how much they dislike the performer. This shift in perception can be chalked up to something specific: A change in his fan base. As Friday Things founder and culture critic Stacy Lee Kong noted in an interview with CBC’s The National after Timberlake’s arrest, while the singer himself might not have changed in recent years, still engaging in the same antics as he always has — co-opting Black culture, disrespecting his wife and just being kind of cringe — his fans have. And they’re now willing and able to see through his BS. “There was a time where I think he would have been able to brush this off as no big deal, it’s a youthful indiscretion, and now I don’t think that’s the case anymore,” Lee Kong said.

We’ve seen this shift in his popularity monetarily, too. In 2018, he released Man of the Woods, his fifth studio album that brought the Tennessee native back to his roots, discarding the R&B influence he’d so heavily leaned on for most of his career for something more folksy (a.k.a. white). The album wasn’t well-received; called a “misstep large enough to merit re-litigating Justin Timberlake’s status as a pop superstar,” by Pitchfork. Ouch. In 2023, the singer — who was in the middle of a world tour for his album Everything I Thought It Was — was ridiculed on social media for his outdated dance moves.

@hannahkosh Immediately no. #justintimberlake #britneyspears ♬ original sound – Hannah

It’s important to note that, of course, we can’t just rag on the star. At the heart of this situation is a man who — as out-of-touch and cringe as he may appear to be — is clearly going through something, and that needs to be taken into consideration and handled with sensitivity and care. (After all, why is a multimillionaire celebrity and father of two driving himself home after a night out in the Hamptons?)

The truth is, those tweens who ogled his crunchy ramen curls when he was leading NSYNC are now full grown adults who have lived through the #MeToo movement and a call for more accountability for those in positions of power across industries. The behaviour, ethics and politics of our former idols have to grow up with us. And if they don’t, they run the risk of being left behind — or publicly meme’d from here to high heaven.

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