Let’s all collectively agree that we loved Justin Timberlake at one point in our youth. Anyone alive during the ‘90s has belted out NSYNC’s “Bye, Bye, Bye,” but now we are starting to see the light. First, there was NSYNC, then Britney, then Janet, and through it all, Timberlake remained untouchable.
However, Timberlake’s image is falling apart as people realize he was never the innocent ex-boy bander recovering from a heartbreak that he portrayed to the public. No one could have imagined that the sweet mama’s boy from Tennessee would do so many awful things just to be famous.
Where Is Justin Timberlake From?
Born and raised in Memphis, Tennessee, Timberlake grew up in a church family. His father was a Baptist church choir director, and he was always surrounded by music. His grandfather introduced him to country artists like Willie Nelson and Johnny Cash at an early age, and from there, his love for singing developed.
Performing as a kid, Timberlake sang country and gospel music. By age 11, Timberlake appeared on Star Search using the stage name “Justin Randall.” However, he started to switch his focus to R&B music. He was inspired by artists like Marvin Gaye, Stevie Wonder, and Al Green.
Their First Interactions
Timberlake’s big break came in 1993 when he became a Mouseketeer on The Mickey Mouse Club. His costars included Ryan Gosling, Christina Aguilera, future bandmate JC Chasez, and future girlfriend and singer Britney Spears. He stayed on the show for two years before leaving to form a boy band.
When Timberlake was 14, he left The Mickey Mouse Club to be in an all-male singing group. He recruited his fellow Mouseketeer JC Chasez to join him in the boy band managed by Lou Pearlman, which eventually became NSYNC. While he seemed like an innocent teenager, something bad was brewing inside him.
Young Love
By the end of the ‘90s, Timberlake and his former costar Britney Spears went public with their relationship. Their young love was highly celebrated in the media because they were both innocent pop star teenagers. Every time they walked a red carpet, everyone wanted to take their picture.
Timberlake and Spears performed at the 2001 Superbowl halftime show with Aerosmith, Mary J Blige, Nelly, and NSYNC. But behind the scenes, things weren’t perfect in the young couple’s relationship. They had both just turned 20 and were thrust into the spotlight at such a pivotal time in their lives.
The Breakup That Shocked the World
After three years of dating, Timberlake and Spears called it quits. Everyone was shocked to hear that they ended things because they were America’s sweethearts. Unfortunately, following the breakup, the only narrative the media heard was Timberlake’s, and he played the victim card. Spears wasn’t allowed to comment on the split.
Timberlake claimed that Spears broke his heart, and he wasn’t shy about playing it up in his interview with Barbara Walters. He also took the opportunity to drag Spears through the mud in the process. The media was already demonizing her because there were rumors that she had cheated on him.
Adding Fuel to the Fire
We later found out that Spears’ PR team wouldn’t let her tell her side of the story. With all the rumors swirling in the media, Timberlake only made things worse when he told Barbara Walters that he wouldn’t reveal why they broke up but said that Spears had done something terrible.
During his interview, Timberlake added more fuel to the fire when Walters asked if Spears “kept her promise to remain a virgin until marriage.” He sarcastically replied, “Sure,” and laughed hysterically. He might claim he hates drama, but that was hard to believe.
Cry Me a River
Although it was never confirmed whether the cheating occurred or not, Timberlake’s breakup song about Spears didn’t quiet the rumors. His hit single, “Cry Me a River,” didn’t bash her, but the music video was unkind and made Spears seem like she had done something wrong.
He hired a cheap Spears lookalike to portray a scene where he walks in on her cheating with another man. He never tried to hide the fact that the woman in the video represented Spears. Timberlake might have been young and dumb, but his actions didn’t match his words.
What Did Justin Timberlake Say to Britney Spears?
Spears was already being scrutinized for her body and sexuality, and she probably confided in Timberlake while they were dating. We can only assume that he was sympathetic until it wasn’t beneficial to his story. Instead of keeping quiet, he committed the ultimate betrayal.
While appearing on a radio show shortly after his breakup, the hosts asked Timberlake if he took Spears’ virginity. Instead of saying it wasn’t his business to discuss her sex life, he said, “Ok, I did.” It seemed like he relished in her pain, and his career skyrocketed.
Gaining From Her Pain
Timberlake used Spears to further his career because he only got more famous from joking about sleeping with her. Timberlake’s solo career flourished from that point, but many believe that wouldn’t have been the case if he had not dated Spears and made a mockery of her after the split.
He played the victim in the situation and was celebrated. Meanwhile, Spears was silenced from telling her side of the story for almost two decades. Unfortunately, Spears wasn’t the only one Timberlake hurt on his path to fame and fortune.
What Did Justin Timberlake Do to Janet Jackson?
The 2004 Superbowl halftime show lives on in infamy after Janet Jackson and Timberlake’s performance ended in scandal. The planned costume reveal went amiss when Timberlake accidentally removed a section of Jackson’s costume and revealed her right breast to 100 million viewers on live TV.
What later became known as “Nipplegate” changed Jackson’s career for the worse, while Timberlake once again gained more fame at someone else’s expense. Jackson left the stadium in tears as soon as the performance ended, but Timberlake stuck around for interviews. He called the evening “fun.”
He Said, She Said
In a post-performance interview with MTV News, Timberlake said, “I am sorry if anyone was offended by the wardrobe malfunction during the halftime performance… It was not intentional and is regrettable.” Jackson’s reps told MTV that she apologized for the incident and would make a statement.
Like Timberlake, Jackson also apologized for the incident. However, her statement clarified that there was an intended costume reveal that MTV had not been made aware of before the show. Therefore, the blame was shifted from Timberlake to Jackson, and an investigation was launched.
The Aftermath
After receiving half a million complaints, the Federal Communications Commission launched an investigation into the halftime performance. Then an MTV executive said Jackson planned the incident and blamed her. Timberlake was seen as the innocent party who was only informed of the stunt before going on stage.
However, Jackson’s team corrected MTV, saying Timberlake knew he was only supposed to pull the top layer of her costume, but it collapsed, and the nip slip was an accident. He played the victim card in typical Timberlake fashion, stating he was shocked and appalled.
Disregarding Jackson’s Feelings
Instead of thinking about Jackson’s feelings while the world scrutinized her, Timberlake said he was frustrated that his character was being questioned. Luckily for him, Timberlake didn’t get the same backlash as Jackson, especially when it was time for the Grammys.
Jackson was scheduled to perform at the Grammys that year, but they asked her to step down following Nipplegate. Timberlake was also set to perform, but he didn’t have the same pressure to bow out of the event. He won two awards that evening and apologized in his acceptance speech.
Fading Golden Boy Status
As the years passed, Timberlake continued to release catchy hits. He eventually understood that Jackson was mistreated after the Superbowl. However, towards the end of the 2010s, Timberlake’s untouchable reputation started to crack. He went from being a pop star to a folk singer.
He lost his mainstream acclaim, and the media coverage shifted from praise to negative opinions of his self-indulgent records. By 2018, the cultural world had evolved from Timberlake, but he hadn’t changed. Many of his actions didn’t match up with the changing times.
Tone-Deaf
In a time when Woody Allen’s inappropriate past was coming to light, Timberlake took a role in his 2018 film Wonder Wheel. He told a news outlet that he wouldn’t get into the allegations in the headlines. The same year, conversations were dominated by the #MeToo movement.
Despite working with Allen, Timberlake wore a Time’s Up pin to the 2018 Golden Globes. He shared a selfie wearing the pin with the caption, “Damn, my wife is hot! #TimesUp.” The post was utterly tone-deaf, and he didn’t even seem to realize why it was inappropriate.
Who Is Justin Timberlake Married To?
Timberlake and his wife, Jessica Biel, have been together since 2007 and were married in 2012. While they have kept their relationship and family private, Timberlake came under fire for cheating allegations in 2019. While working on the movie Palmer, he was photographed holding hands with costar Alisha Wainwright.
The pictures made it seem like there was an intimate moment between Timberlake and Wainwright during a night off. The cheating rumors continued to swirl, so he addressed a statement to his wife and family. However, people saw it as damage control and insincere.
How Many Kids Does Justin Timberlake Have?
After the cheating scandal rocked Timberlake and Biel’s relationship, fans realized that his wife had been pregnant when the incident occurred. The couple has two children together, Silas Randal and Phineas. His son Silas was born in 2015, and Biel gave birth to Phineas in 2020.
The hand-holding pictures came out in December 2019, and their son was born in July 2020. After doing some math, it seems that Biel was a few weeks pregnant when the incident occurred. That must’ve been stressful for the actress, which is dangerous early in pregnancy.
The First of Many Note Apologies
It seems like Timberlake is a huge fan of posting his screenshotted notes on Instagram. After the pictures of him holding hands with his costar came out, Timberlake issued his first Instagram apology. He said he drank too much and had a lapse of judgment.
Timberlake clarified that nothing happened between him and Wainwright. He addressed his wife and family and apologized for putting them through an embarrassing situation, but he didn’t take full accountability because he blamed it on alcohol. Biel never made a public statement about it, but they reportedly started therapy.
Everything Came to a Head
He might have thought the worst of his problems were behind him, but as the #FreeBritney movement grew, and 2021 rolled around, Timberlake’s reputation began to crumble. His reputation was already shaky, and the Framing Britney Spears documentary brought his problematic behavior to light.
The film suggested that Timberlake pushed the narrative that Spears cheated on him with his comments and “Cry Me a River” music video. It also highlighted Spears’ interview with Diane Sawyer, where she took the brunt of the blame for her breakup with Timberlake because she couldn’t talk.
More Backlash Than One Can Handle
After Framing Britney Spears came out, new online fervor against Timberlake was at an all-time high. People took to Twitter to express their distaste for him. They said he had made his career by shaming Spears. It also brought back the Jackson scandal.
Many people on social media labeled Timberlake a “villain” and called him out for answers and an apology. People were rightfully angry because his actions made it look like he stepped on everyone to get to the top without any remorse for his actions.
Another Apology
Due to all the backlash, Timberlake released another apology like his previous apology. However, this time it was a blanket statement directed to all the women he knowingly and unknowingly hurt. He said, “I have not been perfect in navigating all of this throughout my career.”
Timberlake also specifically mentioned Spears and Jackson, stating, “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.” But Jackson, Spears, and Biel weren’t the only ones he offended along the way.
Messy Breakup with Cameron Diaz
After his breakup with Spears, Timberlake started dating Cameron Diaz in 2003. They dated for four years but never made a serious commitment. Their relationship began to crumble in 2006 when Timberlake went behind Diaz’s back and hired Scarlett Johansson for his music video.
The couple announced their split at the beginning of 2007, and the breakup was public and intense. Diaz and Timberlake got into a fight at a Golden Globes after-party after they ended things, and the tabloids ran with it. They went on to work with each other a few years later.
A Possible Affair
Timberlake isn’t a stranger to cheating rumors. While his 2019 cheating scandal has been on everyone’s minds, he was once entangled in reports that he had an affair with Olivia Munn. According to reports, Timberlake allegedly cheated on Biel in 2010.
After meeting at a Myspace event, Timberlake started chasing Munn. She didn’t want to get involved because he was in a relationship. However, he told Munn things were over between him and Biel. They both denied the affair, but insiders said he kept contacting Munn after the fling.
The “Take Back the Night” Controversy
When Timberlake released his 2013 single “Take Back the Night,” many people noticed the title shared its name with an organization working to end violence against women. The organization had already been around for decades, so was it just a coincidence?
Take Back the Night’s lawyers called Timberlake regarding the song’s title and theme because the words were sexual and not anti-violence. Timberlake released a statement saying his song and the lyrics were not affiliated with the organization. He added, “I hope that this coincidence will bring more awareness to this cause.”
Accused of Cultural Appropriation
At the 2016 BET Awards, Grey’s Anatomy star Jesse Williams made a speech about race relations and inequality in America. After the speech, Timberlake Tweeted praise for Williams, saying he was inspired. His Tweet was met with backlash because he clearly didn’t understand Williams’ point.
Everyone on the internet accused Timberlake of cultural appropriation and benefiting from Black culture throughout his career – one of the issues Williams mentioned in his speech. Instead of apologizing, he condescendingly told one of his haters, “we are the same.”
Time for Another Apology
When Timberlake replied to another Twitter user, saying, “The more you realize that we are the same, the more we can have a conversation,” he was then accused of being ignorant. He tried to say that he was “misunderstood” and released a short apology.
He said he was sorry to “anyone that felt I was out of turn” and added that he has nothing but love for everyone. Timberlake walked into that trap, but many of the things mentioned in Williams’ speech were things he had done throughout his career.
Don’t Mess with Rihanna’s Mom
Timberlake might be sensitive when people take jabs at him, but he is not afraid to mock others. At the 2013 American Music Awards, Timberlake raised eyebrows when he did a cringe-worthy impression of Rihanna’s mom. The singer attempted a Bajan accent when collecting his award.
At first, he began his speech with, “Can we talk about how cute Rihanna’s mom is?” He then adopted his version of Monica Fenty’s accent, which caused a stir on social media. Many didn’t think it was polite because she was just there to celebrate her daughter.
He Had Beef with Prince
We hope Timberlake has learned to respect others by now, but he thought he was better than everyone else at the height of his career. After releasing his 2006 hit single “SexyBack,” Prince said, “For whoever is claiming they are bringing sexy ‘back,’ sexy never left.”
Prince’s comments weren’t explicitly directed at Timberlake, and it was a playful statement. However, Timberlake was offended enough to call out Prince in his song “Give It to Me.” The lyrics said, “We missed you on the charts last week, damn, that’s right you weren’t there.”
Taking Cheap Shots
Timberlake was clearly very offended by Prince’s remark about “SexyBack,” so he continued to take jabs at Prince. When Timberlake accepted the Golden Globe for Best Original Song in a Motion Picture on Prince’s behalf (because he was stuck in LA traffic), he took a cheap shot.
As he walked up to the microphone to say a few words on Prince’s behalf, Timberlake stooped lower to imitate Prince’s 5’2” stature. It was unnecessary and childish because he should respect an artist like Prince, who changed the world of music.
No Respect for the Dead
Before Prince passed away in 2016, he said performing with holograms is “the most demonic thing imaginable.” When rumors swirled that Timberlake would incorporate Prince into his 2018 Superbowl halftime show, people assumed he would use a holograph of the late artist.
Although he technically didn’t use a holograph, Timberlake performed with a video projection of Prince as he sang “I Would Die for U.” Many Prince fans were upset because they knew the late artist would have disapproved of the display. After all, he specifically didn’t want that.
Adding Salt to the Wound
During the week Timberlake was set to perform at the Superbowl, he held a listening session for his album Man of the Woods at Prince’s Paisley Park. The late artist’s former residence was an active recording studio and rehearsal space for many iconic performers.
When Timberlake’s listening party was announced, Prince fans were outraged. They thought it was insensitive because Timberlake had dissed Prince multiple times. Others felt Timberlake was disrespectful because Prince didn’t drink or allow alcohol on the building’s grounds, but liquor would be served at the party.
Betting on Jessica Simpson
Back in Timberlake’s Mickey Mouse Club days, he became close pals with Ryan Gosling. The show was a launchpad for many future stars like Spears and Aguilera. Although Jessica Simpson didn’t make the cut, she hung out in the same circle as the Mouseketeers.
After Simpson’s divorce from Nick Lachey, Timberlake was at her house, and they shared a nostalgic kiss. Immediately, Timberlake took out his phone, and Simpson asked what he was doing. He said he made a bet with Gosling when they were 12 on who would kiss Simpson first. She laughs about it now.
Cutting Off SZA
Sometimes, Timberlake doesn’t know when to be quiet and listen to others. During a 2020 appearance on The Ellen Show, he was joined by musicians SZA and Anderson .Paak to talk about the Trolls’ soundtrack. Ellen DeGeneres then started asking SZA about her Rolling Stone magazine cover.
As SZA tried to explain the outfit she wore on the cover, Timberlake kept talking over her. Even worse, he pretended to be SZA by putting on a sassy voice and using the term “sis.” People on Twitter dragged him for his “blaccent” and unnecessarily interrupting the conversation.
Feuding With Kanye
It might not have been Timberlake’s fault, but he and Kanye didn’t get along for a while. After Timberlake released his “Suit & Tie” collaboration with Jay Z, Kanye said, “I got love for Hov (Jay Z), but I ain’t f**king with that Suit & Tie.”
Timberlake didn’t think much about it. He told a radio show, “At the end of the day, it’s just music. I respect his opinion because I think he’s a genius, but I don’t share that opinion.” The two resolved things after speaking at the VMAs.
Shading Las Vegas Residencies
Don’t expect Timberlake to have a residency in Las Vegas anytime soon because he is above that. Many artists have done residencies (similar to a concert tour, but in one location), including Jennifer Lopez, Mariah Carey, Celine Dion, and Timberlake’s ex, Britney Spears.
While many singers have been quite successful with their Las Vegas shows, Timberlake looks at it like a “retirement plan.” During a 2018 radio interview, he said, “You’re planning your retirement. So, for some reason, that feels scary to me.” Maybe he forgot how successful Spears’ shows were.
He Doesn’t Know When to Stop
Maybe Timberlake thinks he is a comedian, but the “jokes” he makes are usually offensive. While introducing Madonna at the 2008 Rock n’ Roll Hall of Fame ceremony, Timberlake made a joke about one of his past girlfriends. Everyone knew he was talking about Spears.
He said, “The world is full of Madonna wannabes; I might have even dated a couple.” Timberlake couldn’t have been more obvious because Spears kissed Madonna at the 2003 VMAs. In a speech celebrating Madonna, he had to tear down other women for some reason.
Everyone Knew What He Meant
It might have been a fun play on words, but everyone knew what Timberlake was implying in a 2014 tweet. He wrote, “A happiest of Bdays to my mother chucking ninja, Madonna! Hope you have a great one, M!” The post sparked immediate backlash for many reasons.
People were outraged because “mother chucking ninja” was another way for Timberlake to say “mother f**king n***a.” He deleted the tweet, but it was too late. Instead of apologizing, he retweeted a post about the Black Lives Matter movement. Who let him have a Twitter account?
That Time He Wore Cornrows
Timberlake has gone through many hairstyles during his career, from his natural curls to the ramen noodle phase to a buzz cut. However, one style caused controversy, and it wasn’t his bleached hair. He once sported a full head of cornrows early on in his career.
While it didn’t cause backlash at the time, the questionable hairstyle choice came back to haunt him in the 2010s. People dug up the old photo to show his history of cultural appropriation. He never apologized but admitted it was a bad choice.
He Was Manipulated
Timberlake’s behavior is inexcusable, but there might be a reason why he has been so problematic. He entered the entertainment industry as a child and was exploited from the beginning. His former manager, Lou Pearlman, had NYSNC sign the worst contract in music history.
Reportedly, NYSNC earned pennies for their grueling hours of work. Pearlman took financial advantage of the boy band, and it was revealed that he sexually assaulted multiple boys whose careers he made. However, Timberlake has rarely spoken about Pearlman since the band broke up.
Trained to Be Neutral
It is also crucial to remember that Timberlake was a product of the child-star system. He grew up with media training, meaning he was taught to stay quiet and listen to professionals. This also meant that his public persona would come across as totally neutral.
Although it doesn’t seem like he was trained to speak to the media, most of the things he said were Timberlake’s way of staying neutral. When NYSNC broke up, his first solo single had mediocre reception, so his publicists recognized that the breakup would be incredible publicity.
He Hated Paparazzi
Timberlake seemed to be in every tabloid in the early 2000s, but it often goes unmentioned that he wasn’t very cooperative with magazines that supported him. He despised paparazzi and once hit a camera out of a photographer’s hands. Now he just keeps his life private.
There was a clear double standard for men and women with paparazzi because Timberlake’s outburst towards photographers was downplayed compared to female celebrities doing the same thing. However, the breakup was a rare time when Timberlake’s team played with the media, snowballing out of control.
Silence No Longer Works
In the past, Timberlake might have been told to stay silent to protect his image, but that no longer works today. Unfortunately, many former fans see his apologies as belated, hollow attempts to take a stance after years of neutrality.
Timberlake is no longer the kind of male pop star people want because he doesn’t have the qualities people celebrate now. However, the personas of today wouldn’t have been accepted in the early 2000s. It seems Timberlake is a product of his time, and he never evolved.
What Is He Doing Now?
After the Spears documentary, Timberlake apologized and laid low for a few weeks before returning to regular posts on social media. Besides teasing new music, Timberlake and Biel recently sold their Hollywood Hills home that Timberlake owned since 2002 when he was in NSYNC.
Timberlake, Biel, and their sons spend most of their time in Montana, where they own a massive home. He also shared a photo of him and Timbaland in a recording studio because they are working on a new album together. Timberlake has worked with the producer many times in the past.
He Got Off Easy
Despite being surrounded by controversy; he has not had a professional demise. Timberlake was able to ease out of the spotlight quietly, an opportunity Spears and Jackson never got. He stepped into the background and barely suffered, unlike the people he hurt along the way.
Timberlake never faced the same harassment from the media as the women around him, and his career didn’t stall. The 2021 Spears documentary might have been damaging, but he apologized and went on with his life and has been promoting new music.