Maybe Justin Timberlake Just Isn't A Good Person

“I’d like to take this opportunity to apologize to absolutely fucking nobody.”

On January 31, 2024, while in the middle of a free concert to promote his then-upcoming sixth studio album, singer Justin Timberlake paused between songs to throw shade.

The “Cry Me A River” crooner, 43, didn’t name the person who stoked his ire to the crowd at NYC’s Irving Plaza, but it wasn’t difficult to connect the dots. Just two days before, Timberlake’s infamous former flame, Britney Spears, took to Instagram to offer an actual mea culpa for being the cause of a three-month-long backlash that Timberlake was dealing with.

In October 2023, Spears shocked readers and most of the internet with revelations about her torrid and tragic life via her New York Times best-selling memoir, The Woman In Me. Naturally, among the many tales in the book were memories of her time with Timberlake. The two began dating sometime before the release of her Oops!... I Did It Again LP, in 2000, and split in 2002. While most of Spears’ recollection mirrored what most remembered of their made-for-paparazzi pairing, there were moments between the two that those outside of their inner circles were completely shielded from.

One of the biggest bombshells in the book centered on a secret pregnancy with Timberlake’s child that Spears; at the time, one of the biggest draws in pop music, was forced to abort. According to Spears, despite being ready to become a young mother, Timberlake, on the cusp of solo stardom, didn’t feel similarly about being a young father. Because of her massive celebrity status, it was decided by Spears’ team that she would ingest pills to cause a miscarriage, as opposed to seeking proper medical care and getting an abortion.

“When I tell you it was painful, I can’t begin to describe it,” Spears shared. “The pain was unbelievable. I went down to the ground on my knees, holding the toilet. For a long time, I couldn’t move. To this day, it’s one of the most agonizing things I have ever experienced in my life.”

As she lay on the bathroom floor, writhing in physical and emotional agony, Timberlake attempted to soothe her by, of all things, sitting by her pained body and strumming his guitar. Spears claims she doesn’t remember how it all ended, but the memory and fear of the incident have stuck with her for more than 20 years.

Just months later, Timberlake ended their relationship via text message as she filmed the “Overprotected (Darkchild Remix)” music video.

When Spears’ fans learned of the terminated pregnancy from a book excerpt shared with the press weeks before its release, they, unsurprisingly, swarmed Timberlake’s social media accounts with hate comments and threats. To this day, they are ongoing.

Spears, in an attempt to quell her faithful followers, took to Instagram on January 29 to offer a public apology and overly praise the first single from his new album, “Selfish,” which had just been released.

“If I offended any of the people I genuinely care about,” Spears wrote, “I am deeply sorry.”

Two days later, Timberlake took the stage at his NYC show and gave his fiery response. Fan videos of his non-apology went viral, and once Spears caught wind of it, she angrily rescinded her apology and threatened to make him cry to his mom ("B-Girl ain't lost the beat...")

Spears’ fans, meanwhile, continued to take matters into their own hands by raising a deep cut from her 2011 Femme Fatale album, also titled “Selfish,” up the US iTunes charts. Within hours, Spears’ “Selfish” hit no. 1. Timberlake’s “Selfish” would peak at no. 3.

It is safe to say that the past few months have not been kind to Timberlake. Once able to brush off most dirt that came his way with his blue-eye soulful falsetto and country-boy good looks, the Grammy-winning entertainer now weathers the physical features of someone who has seen better days – and no, that’s not a nod to the song Timberlake and his *NSYNC bandmates cut for the 2023 Trolls Band Together soundtrack.

His sixth album, Everything I Thought It Was, was released in March. It was considered a dud by most, despite an impressive top-five ranking on the Billboard 200 and another assist from current-day *NSYNC with the album track, “Paradise.”

“Selfish,” the first offering from the set, barely cracked the top 20 on the Billboard Hot 100. A follow-up, “No Angels,” peaked at no. 19 on the Bubbling Under 100 Hot Singles list – not exactly what one hopes for from a return to music after a six-year break.

Timberlake’s Forget Tomorrow World Tour, meant to promote Everything, appeared to be the bright spot in a mass of mess. Unfortunately, future outings are now up in the air following Timberlake’s surprising DUI arrest on June 19 (he did, however, make the first of two Chicago appearances on June 21).

To add insult to injury, media reports from his recent arrest claim that Justin, in a moment of frustration and alleged inebriation, complained that being taken into custody could put a dent in his tour plans. According to those same reports, the arresting officer, who was too young to even know who Justin Timberlake was, asked in response, “What tour?”

If you’ve ventured into certain online spaces recently, you’ve most likely come across meme after meme featuring Timberlake’s actual mugshot from the arrest making the rounds (I’ve admittedly shared a few on Twitter). While those opposed to the entertainer have been riding a schadenfreude high since March, they’ve since been boosted to even higher heights of vengeful glee following Justin’s latest misfortune.

As some laugh at his pain, Timberlake’s strongest supporters have gone on the offense, criticizing those joking about the arrest and his other recent adversities. They also widely question how anyone could “hate on” Timberlake, who, in their eyes, has done nothing worth the ongoing vitriol.

With this question in mind, I’d like to take this moment to respond to those who feel that the onslaught against Timberlake is far too much.

People, maybe it’s possible that Justin Timberlake just isn’t a good person.

Believe it or not, I didn’t always feel this way about Justin. Like so many of you, I, too, was a huge fan of his talent and curly-haired cuteness during the Total Request Live era. That appreciation extended to the solo career he embarked on that the actual best singer of *NSYNC deserved way more than him (we’ll get back to this a little later). I’ll even go on record and say that his icon-making 2006 FutureSex/LoveSounds album still stands as his most stellar work. I do not deny that for all of his faults, Justin Randall Timberlake did the work and then some, and reaped the benefits of that work.

Inversely, the main offense that has irked me about Timberlake for some time connects to all of the people he nearly ruined on his way to the top; none more so the women who helped lead him there, and how he continues to jab at the sores he caused. Timberlake does far too much to keep his grip on a status that has long faded. Time and tastes have moved on as they naturally do. It’s Timberlake who hasn’t or rather can’t, and he has yet to fully acknowledge the wrongs that permanently altered the lives of three amazing entertainers, including one who sang at Justin’s side for years.

Case No. 1: Britney Spears

Naturally, many of Justin’s supporters feel that Britney Spears and her fans are still deep in their feelings over their 2002 breakup, the actions that led to the dissolution, and Timberlake’s response to it all – a.k.a. his biggest hit, “Cry Me A River.”

For the record, they’re not completely wrong, but the story goes a lot deeper than “boy meets girl, girl (allegedly) breaks boy’s heart, boy records scathing ode that twists the narrative and makes girl the target of misogyny that she still takes on to this very day.”

Back in my time, a music video could easily make or break an artist. Timberlake, a veteran of the industry by the time of 2002’s Justified, his first solo project, was well aware of this. His first offering, the dance-heavy “Like I Love You,” was a decent reintroduction, but chances are you barely remember the clip, which mostly centers on Timberlake hitting on a girl outside of a 7-Eleven.

Justin knew that his next move had to be huge, or it could be his final move as a solo star. Using his private life with Spears and the shit storm he partially caused by sharing intimate bits of their relationship with whichever radio personality would give him the most spins, Justin teamed up with director Francis Lawrence to dig the knife even deeper with the dark visual for “Cry Me A River.”

The video, as we all know, sees Justin in full stalker mode, walking into the home of a woman who looks eerily similar to Spears. He then follows her around the house without being noticed, getting close enough to sniff her hair at one point. The clip ends with Britney’s double stepping out of the shower to find a looped video playing of Timberlake kissing a woman with dark hair, rumored to be a likeness of Charmed star Alyssa Milano. The two had a short fling sometime after his breakup with Spears (Spears alludes to the pairing without naming Milano in The Woman In Me).

Before its release, insiders at Jive Records – Timberlake and Spears’ then record label – believed the “Cry Me A River” visual would cause Spears, then the bigger artist of the two, more than a bit of grief. They rightfully reached out to inform Britney of Justin’s big move, but were shocked to learn that Timberlake beat them to the punch.

“[Justin] called me up, and [said], 'And by the way, you’re in a video [of mine] that’s coming out,” Spears shared with Rolling Stone in 2011.

“’Don’t worry about it,’” Justin assured her. “’It’s not a big deal.’”

Britney says that Jive staff then gave her a choice.

“If you want to change [the video],” she relayed, “you can.’”

Out of kindness and probably warm feelings for Timberlake, Britney chose to let the “Cry Me A River” video air without interference. She would soon realize her mistake of not viewing the video before giving Jive the okay to ship it out.

“[The video] came out,” she remembers, “and I said, 'I should’ve freakin’ said no to this shit!' I was so like, 'Woah. What is going on right now?'”

To the shock of absolutely no one, the “Cry Me A River” video did exactly what it was meant to, boosting Timberlake from former teenybopper to superstar overnight. Timberlake has never directly stated who the inspiration behind the song is, but his close friend Tim "Timbaland" Mosely - who produced and appears on the track - did so for him in 2015.

Truth be told, Spears is also one of the biggest influences behind Timberlake's entire career.

Before a note was ever recorded for what would become Justified, Spears’ involvement in Justin’s life granted him access to an entertainment scope well beyond the rivers and the lakes he was used to via the TRL crowd. Spears, admittedly, also used the relationship to pivot into more mature waters, but other than the occasional response to Timberlake’s digs, she was never as crude or disrespectful as he remains toward her to this very day.

In 2007, as he accepted an award at the Brits, Timberlake called out an unnamed party (clearly Spears, who was dealing with more than a few troubles) about their supposed issues with alcohol.

“Stop drinking,” he chastised while pointing his finger at the camera, “you know who you are. I’m speaking to you. You’re gonna get sloppy.”

Not even 24 hours after his DUI arrest, sources from Timberlake’s camp specified that Spears’ memoir and the public reaction to the section about Timberlake had a hand in the decline of his album sales, and his alleged uptick in drinking. At his June 15 show, the last before his arrest, Justin sang “Cry Me A River” - just as he always has - as part of his set.

Case No. 2: Janet Jackson

In February 2004, at the apex of her massively successful career, legendary music superstar Janet Jackson had everything she had built throughout her 30-plus years in entertainment, snatched away from her.

We all know where it occurred. We all know what occurred. We also know that Justin is not at complete fault for what occurred during the performance. That’s not what this is about. We’re not speaking of the incident itself. What we will speak on, however, is everything that occurred immediately after the performance.

As Jackson and Timberlake both hurried off stage at the Reliant Stadium in Houston, TX, Access Hollywood managed to catch the latter act on his way to points unknown. When asked if that moment during the performance was purposeful, a sly Timberlake looked to the camera and said, “Hey man, we love giving y’all something to talk about.”

From that moment on, an avalanche began that would end with Janet Jackson; then one of the biggest stars in the world, only comparable to her older brother Michael, being blacklisted on radio, television, and red carpets for years to come. There is proof of this. Google is your friend. We will not be arguing about this.

Timberlake, meanwhile, became music’s it boy, starting with his first Grammy win just one week after Super Bowl XXXVIII. Janet was also meant to appear at the ceremony to honor longtime friend and collaborator Luther Vandross. After Jackson’s refused to honor requests from the ceremony's producers to apologize during the telecast – because she had already done so - her invite was allegedly revoked. Timberlake, being offered the same terms, took the opportunity and apologized while accepting his Grammy.

Janet would speak on the Super Bowl incident for the very first time with Oprah Winfrey in 2006. During the conversation, Jackson shared, among other things, how she was “left hanging” by Justin after the performance.

“I considered him a friend,” she said with visible sadness, “and you just don’t do that to a friend.”

Those would be the only comments we heard publicly from Jackson until 2023 when she addressed the matter once again in her four-part Lifetime docuseries, Janet Jackson.

In the final episode, we learn of Timberlake reaching out to Janet in late 2017 to invite her to join him on stage for his own 2018 Super Bowl Halftime performance (Jackson was rumored to be banned from all NFL events after 2004, but the NFL waited until 2017 to insist she never was). She gracefully declined Timberlake's invitation, believing there was nothing good about revisiting that time in her life.

Jackson then recalls when Timberlake first reached out to some time after the 2004 NFL Halftime Show.

“[Justin] said, ‘I don’t know if I should make a statement [to the media],’” Jackson claimed to her older brother, Randy. “I said, ‘Listen, I don’t want any drama for you. They’re aiming all of this at me. If I were you, I wouldn’t say anything.’”

The segment ended with Jackson referring to Justin as a “good friend,” despite us now knowing that Timberlake ultimately refused her advice.

Justin, in actuality, said a lot of things about the performance in the days following. The first and most notable was with Entertainment Tonight, where he seemed all too ready to throw Jackson under the bus.

“I don’t feel like I need publicity like this,” he stated with all the Blackitude his white body could muster. “And I wouldn’t be involved with a stunt, especially something of this magnitude.”

Throughout the ET interview, Timberlake exuded various levels shock and disgust over the performance (“My entire family was there,” he even opines at one point). After playing up to the camera a bit longer, ET ends the interview… but Justin, having more to say, comes back to the camera and continues to unload about his “friend.”

And then, there was the song. Oh, sweet Damita Jo, that damn song.

In 2011, Timberlake collaborated with FreeSol; a neo-soul artist he discovered and signed to his now-defunct Tennman Records, on the track, “Role Model.” In one of the song’s verses, Justin makes light of the Super Bowl incident as only an asshole would – and I’m using his direct vernacular, by the way.

“Maybe you're right, maybe I'm an asshole/Oops, did I take it too far? Super Bowl,” he raps in the song.

As Justin performs the verse in the music video for “Role Model,” a woman wearing a football jersey lifts her shirt to expose her (censored) breasts.

Oh, and did I fail to mention that like Britney before her, Janet had a direct hand in guiding Justin to the fame that ultimately screwed her over?

“*NSYNC opened for me,” Janet mentions right before she talks about their phone conversation in the Janet Jackson docuseries.

She’s right, by the way – they opened for her on select dates of Janet’s 1998 The Velvet Rope Tour. At the time, it was *NSYNC’s - and Timberlake’s - largest audience to date.

As he not-so-secretly started work on Everything I Thought It Was in 2021, Timberlake released a public apology to both Spears and Jackson on social media. The note came two months after Hulu documentaries based around Spears’ conservatorship and the actions that led to it (Framing Britney Spears), and Jackson’s Super Bowl fiasco (Malfunction: The Dressing Down of Janet Jackson), made their debut.

“I understand that I fell short in these moments and many others, and benefit from a system that condones misogyny and racism,” he wrote in part. “I specifically want to apologize to Janet Jackson and Britney Spears both individually, because I care for and respect these women, and I failed.”

At some point after Britney’s memoir dropped, Timberlake deleted the apology from his Instagram profile.

Case No. 3: JC Chasez

Following Timberlake and Jackson's 2004 Super Bowl performance, second-frontman and better vocalist of *NSYNC, JC Chasez, was in rehearsals for his own potential career-changing performance.

After taking a backseat to Timberlake for years, Chasez went on his own solo path, starting with the hip-hop/college marching band-influenced “Blowin’ Me Up (With Her Love)” from the 2002 Drumline soundtrack.

The odd mash-up of genres was intentional. The tune, which would become JC’s first (and only) top 40 Billboard hit, was a tease of the eclecticism to be heard on Chasez’s future full-length debut - 2004’s Schizophrenic.

Yes, we’re aware the title is in poor taste, but the early 2000s were a different time.

Boosted by the popularity of “Blowin’ Me Up” and eventually with an actual first single from Schizophrenic to push - the fetishizing but catchy “Some Girls (Dance with Women),” featuring the late Dirt McGirt (a.k.a. Ol’ Dirty Bastard – again, the 2000s were a different time), it was only fair that Chasez, like Timberlake, have the opportunity to strut his stuff on a national stage.

He would get that chance through an invite to perform at the 2004 NFL Pro Bowl, taking place in Hawaii at the start of February.

By this time, the NFL was taking no chances following the incident with Timberlake and Jackson, which occurred three days before the Pro Bowl. Noting the somewhat raunchy theme of “Some Girls,” which JC was planning to perform, the game’s organizers asked him to alter some of its lyrics.

Chasez obliged, but then was asked to nix the song altogether and instead perform “Blowin’ Me Up.” Once again, Chasez did as asked, but was approached again by the organizers to change or omit his lyrics – specifically, the line, “Look at shorty, she was leaning on me/ Getting horny, maybe we'll get naughty.”

It’s uncertain if Chasez was able to find a workaround, but it was all for naught anyway. Taking the overly cautious route, the Pro Bowl ultimately canceled Chasez’s performance altogether.

Schizophrenic was released at the end of February. Despite high marks from critics, it performed poorly, peaking at no. 17 on the Billboard 200. A follow-up single, “All Day Long I Dream About Sex” – yes, there were a lot of songs about sex – was only released in overseas markets. Stateside, the album was soon forgotten about.

Not taking the loss sitting down, Chasez immediately went to work on its follow-up, a less-sensual, more sonically linear concept album titled The Story of Kate. To assure himself a bit more success, Chasez worked with a who’s who of producers and writers of the time, including Timbaland, Dallas Austin, and, of course, Justin Timberlake.

Speaking in an interview in 2006 as sessions for Kate continued, Timberlake praised Chasez and confirmed what most *NSYNC fans have been saying for decades.

“In my opinion, [JC] had the best voice out of all of us,” he told MTV. “Out of all the boy bands, call 'em what you will, he was the one that could out-sing all of us. In my opinion, he had the best voice out of all of us. It was fun to sit behind the board and push him [vocally].”

Like Schizophrenic before it, which was pushed back numerous times before its final release date, Kate was repeatedly held off from its planned 2006 due date. No official word was given as to why, but it seems plausible that another release from Chasez’s label, Jive Records, that same year may have taken precedence – that would be Timberlake’s FutureSex/LoveSounds, which arrived that September.

Frustrated by the lack of support from Jive and the alleged leaking of several songs from the album, Chasez asked to be released from his contract with Jive. He has not put out an official solo project since and The Story of Kate was shelved indefinitely (it has since leaked in its entirety). There’s a lot more to Chasez’s sad situation, including how Timberlake and his monster career tie into it, but I believe enough has been said in this section. For more info, feel free to check out the two-part YouTube fan documentary, “Dirty Poplitics and the Solo Career of JC Chasez.”

Conclusion:

It isn’t lost on me that of all the days for his arrest to occur, Justin Timberlake was booked one day before Juneteenth, a national holiday that commemorates the emancipation of enslaved people in America.

In recent years, Timberlake has been noted in many Black circles as being a “culture vulture,” someone - usually white - who steals bits and pieces of a marginalized community's style, traits, language, and overall sense of being, and uses them to great effect without properly acknowledging or giving respect to the community they grievously took from.

In my humble opinion, it is one thing to gain entry to our spaces either by invitation or privilege and use parts of our essence to mold yourself into a whitewashed knockoff that, on more than one occasion, comes across as parody.

It is another thing altogether to use our culture to not only boost your career and the white hype surrounding it but also continue to disrespect multiple people who assisted in making you the artist you are, including but not limited to:

1. the Black woman who put you on your first national stage.

2. someone directly inspired by that Black woman who is now attempting to heal from years of horrible trauma – some of which you directly caused - and,

3. the talented friend you only seem to call on when you need some good press.

And let’s not even get started on that whole Man of the Woods era… because that in and of itself can be another lengthy dragging that Timberlake rightfully deserves.

Similar to what Jennifer Lopez is currently going through, no one is truly “hating” on Justin Timberlake. The negative feelings many have regarding him are both justified and valid.

Janet Jackson’s fans are still on his ass because he has yet to display true growth to Janet or her fans since that moment in 2003 – one he could’ve made easier for Janet by simply shutting the hell up.

Fans of Britney Spears are still raging in his comments due to the song he wrote about their relationship in 2001 that he occasionally continues to preface with nods to her alleged infidelity. This is the same woman who was forced to give up their child, and still feels every ounce of hurt and pain from the experience more than 20 years later.

Some (but not all) *NSYNC fans are still giving him the side-eye for doing the absolute least for someone far more talented than him, even though he had more than enough pull in the industry over the years to do so. And let’s not forget how Timberlake constantly teases a full-blown *NSYNC reunion, only to never follow through (to add to this, the way the group was credited as “*NSYNC feat. Justin Timberlake” on the Trolls Band Together soundtrack – anyone else getting “Jai Ho” vibes?)

Folks have been waiting for decades for just an ounce of true accountability and growth that Timberlake doesn’t renege on whenever shit gets real. At what point does the maturity show up and stick around? Has the maturity ever even been in the room with us? Justin is now 43 years old, married, and a father of two children. If for no one else, two people in his direct life should invoke a deep need for him to be the best person he can be.

Instead, he now has alleged sources blaming his alleged alcohol troubles on someone he hasn’t been in the same room with for almost 20 years. Make that make sense.

Not to mention, these past mentions aren’t even the tip of the iceberg when it comes to this dude. Perhaps you may have forgotten about:

• The time Prince jokingly reminded fans at one of his concerts that “sexy never left.” This led Justin to then make fun of Prince’s height at an awards show, record a diss track against him, allegedly serve alcohol at a listening party held at Paisley Park following Prince’s death (Prince was known to be staunchly against alcohol consumption), before following everything up with a “Purple Rain” tribute to Prince during his 2018 Super Bowl Halftime performance.
• The infamous Jesse Williams’ 2016 BET Awards speech debacle, where the Grey’s Anatomy star addressed cultural appropriation and systemic racism. Timberlake, feeling “inspired” by Williams' speech, took it upon himself to immediately jump on Twitter after and share his feelings – despite being the exact type of person who benefits from the things Williams mentioned in his speech.
• Timberlake’s response to Black writer Ernest Owens regarding Williams’ speech, who pointedly reminded the singer of his “culture vulture” status. Owens was then grossly patronized by Timberlake (“oh, you sweet soul”), then played the victim once other Black Twitter users attempted to put him in his place (“I feel misunderstood. I shouldn’t have responded anyway”).
• The cornrows era and the whole “fo shizz, fo shizz” thing. Why did y'all let him act like that?

In the past, I have been guilty of allowing the sweet haze of nostalgia to block out some harsh truths. Just last week, I broke down how my affection for Paris Hilton and her 2006 debut album is now forever marred by the multiple overly racist acts she has yet to apologize for. At some point, we have to face the reality of the celebrities we idolize and how our emotional ties to them; whether nostalgic or otherwise, cannot be the sole trait we judge them through.

Many of you have given Justin Timberlake multiple passes on his bad behavior because he sings and dances well (well, most of the time), and maybe because “SexyBack” was your anthem that one summer. While I do have empathy for whatever demons he allegedly may be battling, that does not give him the right to continue to act out in Black spaces or any other space - period.

Until he acts right, the memes will continue, the laughs will grow louder, and his karma will persist in making his remaining time in the spotlight a living hell. When all is said and done, maybe Justin Timberlake just isn’t a good person. And maybe, just maybe, it’s time for everyone to finally wake up and realize this.