Little-Known Backstage Details About *NSYNC

For many of us, *NSYNC were the definitive soundtrack to the late ’90s. We swooned over Justin and JC. We learned all the dance moves. And, rather unfortunately, many of us even copied their fashions. But while the boyband spent years in the spotlight and on the road together, how much did the five really get along? We’ve got all the juicy backstage gossip with these little-known details about Lance, JC, Joey, Chris, and Justin.

Justin didn’t send his bandmates wedding invites

It seemed rather shocking when, in 2012, Justin didn’t invite his old bandmates to witness him tie the knot with Jessica Biel. But the boys have nevertheless claimed that they didn’t feel snubbed at all. Rather, they understood a reunion of the band would have caused a complete and total media frenzy that would distract from the blushing bride. "[Justin] wanted that wedding to be about Jessica," Lance later explained.

"He didn't want it to be an *NSYNC reunion." But it's not as if the band was shunned altogether. As an alternative, they all attended the engagement party instead.

Chris Kirkpatrick was the true stud of the group

While Justin may have had the golden curls and JC the bedroom eyes, it was Chris Kirkpatrick who was the real stud of the group. In an appearance on Watch What Happens Live, Lance Bass revealed that Kirkpatrick was a bit of a player – although things have changed for the ladies' man since his boyband days.

"He's a Casanova!" Lance revealed. "You know, before [his marriage]," he clarified. "He's married to a lovely wife now, but he was single before." Yep, Chris has been married to Karlyn Skladany since 2013.

Timberlake regrets the awful fashions *NSYNC inspired

Perhaps even more memorable than their music were *NSYNC’s, questionable fashion choices. From music videos to red carpets to concert stages, the boys weren't afraid to experiment when it came to fashion. Patterned suits, snakeskin pants, and rainbow-hued trench coats, anyone? The band’s fashion was so bad, in fact, that in a 2017 interview with The Hollywood Reporter, Timberlake made a humorous apology for inspiring some truly hideous ’90s trends.

"There was maybe a period in the '90s where I could skip over some of the outfits that were public," Timberlake admitted. "But... the internet will never let me."

The band were accused of plagiarism

The song “Up Against the Wall” appeared on the hit record Celebrity, but the band members really found themselves up against a wall when they were slapped with a lawsuit by musician Troy Alexander. Alexander claimed that he played *NSYNC's record label a demo of a song with a similar melody and the same name back in 1990.

Back in 2007, the record company Jive claimed that they weren't even aware of the copyright claim. Yikes. It's unclear how the lawsuit played out, but it's safe to say that the band escaped from the incident pretty much unscathed.

Timberlake hurt his bandmate’s feelings

Fans weren’t the only ones upset when Timberlake broke up the band. In his memoir Out of Sync, Lance Bass admitted that he had been really hurt when Justin walked away from the group. “I felt completely betrayed,” he wrote. “Why couldn’t Justin keep the franchise intact while he also did his own thing?” It was a question lots of people were asking at the time, and years later, Justin gave an answer.

"I felt like I cared more about the music than some of the other people in the group," Timberlake told The Hollywood Reporter. "And I felt like I had other music I wanted to make and that I needed to follow my heart." At least now we know why he really said “bye bye bye” to the boys.

Some of the band almost appeared in a movie

One of the producers of Star Wars: Episode II – Attack of the Clones had daughters who were huge *NSYNC fans. And so Chasez, Kirkpatrick, Joey Fatone, and Fatone's brother Steven got to don Jedi robes and swing sabers. Alas, the scene was eventually axed from the film – allegedly due to protests from hardcore franchise fans.

"They cut it out because we were [SAG-AFTRA members]," Fatone later said at Fandemic Tour Atlanta. "Usually, they have to pay the SAG rights to it." And apparently, the producers weren't willing to pay them solely for a cameo!

Fatone’s brother had a pretty embarrassing Jedi experience

While the *NSYNC footage was ultimately cut from Attack of the Clones, the story of Fatone’s brother Steven lives on in infamy. Steven was so incredibly excited to be swinging a lightsaber that when he went to do a scissor kick, he actually lost control of his bowels. "It was pretty embarrassing," Steven later admitted. But he ended up being able to turn a negative into a positive.

When he found out that his scene wouldn't be in the film, Steven made a photoshopped shirt showing the band as Jedi warriors, plus Britney Spears as Padmé Amidala.

Lance Bass stayed in the closet for the sake of the band

Lance Bass is now out and proud, and his wedding to Michael Turchin even got its own E! special back in 2014. But back in his boyband days, the singer kept his sexual preference under wraps for fear that it would destroy the group if he came out. At the Hollywood Walk Of Fame ceremony, Bass said, "I'm gay! And at the time, I thought that I would never be able to tell anyone."

"Not only was I terrified of the lasting rejection... but more than that I didn't want to jeopardize the careers of [Fatone, Timberlake, Kirkpatrick, and Chasez), much less the hundreds of amazing people who worked tirelessly to bring *NSYNC to the world."

The boys took legal action against their manager

Lou Pearlman was the brains behind both The Backstreet Boys and *NSYNC, but his relationship with the latter soured in 1998. That was the year in which *NSYNC sued Pearlman for fraud, claiming he had stolen half of their earnings. In the end, the case was settled out of court; Pearlman, however, was eventually convicted of money laundering and passed away in prison in 2016.

This must have been a confusing and painful time for the boys, but it all worked out in the end: by 2000, the group came out with a brand new album via Jive Records, and the record — "No Strings Attached" — turned them into superstars.

Bass claimed their former manager behaved inappropriately

Pearlman's bad behavior seemingly knew no bounds, as Lance Bass let it be known that in their younger years, he and other bandmates had received some unwanted attention from their manager. He told The Hollywood Reporter that while Pearlman never fully “crossed that line” with him, he had heard stories of his lack of boundaries with other young boys.

"He was creepy," Bass said later said of Pearlman during an appearance on Access Hollywood. "He was a very touchy-feely guy... he was always giving you shoulder rubs and stuff like that. He was definitely creepy."

The band bonded over Halo

What else would you expect from a bunch of teenage boys trapped on a tour bus? Bass once revealed that when the band toured, they would hang out in their bunks and play games from the Halo franchise against one another, sometimes for hours at a time. "We had a different console in every bunk, so we'd play Halo against each other in our bunks," Bass told Travel + Leisure.

"It was the scariest thing in the world because everyone is in their own little world on this bus just sniping each other. We'd play for hours."

Being in a boyband isn’t the key to a good night’s sleep

Apparently, dancing and singing in front of millions of screaming fans isn’t the best way to catch some peaceful Zs. Bass revealed that after shows the band would be left completely hyped up. Plus, he said that so many nights on the road have now permanently conditioned him to need background noise in order to sleep. "If anything is moving, I'll fall asleep immediately," he told Travel + Leisure.

"If I'm sitting there and it's quiet, I can't sleep. I have to have a sound machine on at all times. On a plane I'm out — that's my favorite."

Timberlake believed he didn’t have the best voice

Both Timberlake and Chasez went on to pursue solo careers, but while the latter’s fizzled out, Timberlake, of course, went on to become one of the biggest pop stars in the world. That said, it may surprise fans to know that even Timberlake himself believes Chasez to have the better voice. He said so outright in a 2016 interview with MTV.

"He has the best voice out of all of us," Timberlake claimed. "Out of all the boy bands, call 'em what you will, he was the one that could out-sing all of us... and I've known him since I was 10."

They made it in Europe before they made it anywhere else

*NSYNC first broke Europe before they made it big at home. And when the band arrived on foreign shores, they’d be greeted by thousands of screaming fans. It took a bit longer for them to break the U.S., however. In fact, Kirkpatrick admitted that in the early days the band would only have a few people waiting for them when they landed back in America: their parents.

The group knew they had a tough job ahead, which was to be real competition to the Backstreet Boys. And *NSYNC made their American debut right back where their band began: In Florida, specifically in Disney World's Pleasure Island.

The band’s diet wasn’t the healthiest

You wouldn’t have known it to look at them, but back in the day, the boys ate a considerable amount of junk. Indeed, Fatone has said that their tour bus diet was fit for a four-year-old, containing lots of chicken nuggets, grilled cheese, and mac n’ cheese. No word on whether the nuggets were shaped like dinos, though. Nowadays, Fatone's tastes haven't evolved all that much, either!

"Don't ask me why, but I just had a craving for Fruity Pebbles," he told Mashed in 2022. "If I had a guilty pleasure, something like a staple or something that I would order all the time, definitely a chicken parm."

Fatone was the biggest flirt

While Kirkpatrick might have been the biggest player in the group, Fatone has named himself as the biggest flirt. In an interview with US Weekly, he said he was a pretty flirtatious guy back then. He maintained Chasez was as well, though, but that he was just more “stealth” in his tactics.

"[JC] was very stealthy about when he would hang out and be flirtatious with somebody," Fatone said. He said that Chris, meanwhile, "was a troublemaker."

One of the band members lost his temper with a fan

Life in a boyband may not be all it's cracked up to be. Sure, you have millions of adoring fans, but sometimes those devotees forget that you're still just a human being — and vice versa. Justin Timberlake and a — we can only assume, former — fan of his learned this the hard way. The normally-cool Timberlake was accused of losing it when a jokey comment didn't land right.

Back in 2001, an eagerly-awaiting 15-year-old felt snubbed by the singer, so she decided to shout after him, “J.C. is cuter anyway!” And according to her, Timberlake then pushed her against a wall and berated her. Definitely not the right move, J.T. Consequently, she sued for assault.

The band may finally reunite

In 2023 the boy band that "temporarily" went on hiatus back in 2002 dropped some seriously exciting news: they're finally reuniting! Well, for one song, anyway. Yep, the group reunited to record a brand new track for Timberlake's film Trolls Band Together. The song, "Better Place," is the band's first tune in over two decades.

And it may not be their only new release, either. The entire Trolls Band Together soundtrack could feature even more new tunes from everyone’s favorite ’90s boy band!

One of *NSYNC’s hit singles was intended for the King of Pop…

“Gone” was one of *NSYNC’s most memorable hits, but what many don’t know is that Timberlake actually wrote it for his idol Michael Jackson instead. With his showmanship and impressive high notes, we can see how MJ influenced Timberlake's musical style! Timberlake was undoubtedly crushed when MJ’s management team ultimately passed on the tune. But Timberlake still got to make his Michael Jackson dreams a reality, albeit in a strange way.

You see, Justin Timberlake did get to collaborate with Michael Jackson on a song... in 2014, five years after Jackson's death. The duo's vocals were spliced together to form the dance tune "Love Never Felt So Good," which was warmly received by critics.

. …and Timberlake wrote it while pining for Britney

Timberlake made it very clear just how crazy he was about his then-girlfriend Britney Spears. But in case you weren’t convinced, he apparently wrote the almost-MJ-tune “Gone” while she was away and he was missing her terribly. Now that's love! She must have been on tour halfway around the world, right? Nope! Apparently, she was taking a little too long… at the hair salon.

Clearly, the couple were very much in love at that time. But after three years, the love apparently fizzled away, and Justin and Britney broke things off in 2002.

It hit us at just the right time

Timberlake and Spears started dating in 1998. According to several sources, their romance began when Spears was on tour with *NSYNC. Their stars were on the rise at the same time; she was just about to make it big herself with her hit single “… Baby One More Time,” which hit the airwaves that year. It was like nothing else around.

At the time, Aerosmith, The Goo Goo Dolls, the Spice Girls, and *NSYNC were the ones to beat. So there arguably wasn’t much music out there that appealed to the typical tween and teenage girl. You know, the kind of music made by teens, for teens. But Spears was different, and she was about to change the game.

She changed MTV for good

Then, of course, there was that video. You know, the one with 16-year-old Spears dancing about in a school corridor? It genuinely took the world by storm! However, not everybody was happy about it.

Music expert John Seabrook told Entertainment Weekly in 2018, “MTV had, up to that point, tried to resist mainstream pop, because they wanted to be perceived as cool… But I think with Britney, and the video in particular… it really changed MTV.”

It was an instant phenomenon

No matter what MTV’s idea of “cool” may have been before, Spears and “… Baby One More Time” redefined it. The song reached number one in multiple countries across the globe, fueled by rabid fandom and not a little controversy.

The single sold 500,000 copies on its very first day of release in the U.S. And, of course, that’s the kind of success that can change a life in many different ways.

The famous cover of Rolling Stone

For its retrospective on “… Baby One More Time,” Entertainment Weekly spoke to John Ivey, president of CHR programming for iHeartMedia. He remembered, “Britney had the second level. People saw this video and thought, what is this girl? Because everybody latched onto this immediately,” he continued.

“It wasn’t very long after that, she was on Rolling Stone.” See? Game. Changed. And if the single was seen as racy before, Spears’ Rolling Stone cover tipped it over the edge.

Crowning the princess of pop

Spears had suddenly gone from being a complete unknown to one of music's biggest stars. The media swiftly dubbed her “the Princess of Pop,” and it was a title that seemed to suit her.

This ushered in an era where other female singers tried to emulate her success — think Mandy Moore, Christina Aguilera, and the like. But Spears remained the ruler of that particular music scene for quite some time.

Free Britney

Times have, of course, changed a lot since 1998. “... Baby One More Time” is still a popular song — one of the classics of its genre — but the passing of the years has not been kind to Spears or her most famous track.

It’s the sort of tune you might find yourself humming without really paying attention to the lyrics. But public perception of the song has evolved — as has the perception of the young woman who sang it.

More than the sum of her parts

Much has been made about how much agency Spears ever had over her career, too. Some people wondered, was “… Baby One More Time” a hit because of her talent and media savvy, or because of external forces? Other commenters couldn't help but wonder if Spears was actually a carefully constructed product made to appeal to teenage girls by the music overlords.

Well, the answer to the first question is complicated. But the answer to the second question would appear to be “no.”

A star is born

In Entertainment Weekly’s 2018 piece about the creation of “… Baby One More Time,” the publication spoke to all of the people who’d had a hand in the song and video. The resulting oral history holds the key to understanding its appeal. Joe Levy, a Rolling Stone editor, said, “Britney Spears is someone who, from the time she was a child, wanted to be a star."

Barry Weiss — the president of Jive Records — remembered meeting the young Spears for the first time when she came to do an audition, too.

She was the right person at the right time

Weiss said, “[Spears] was wearing a black cocktail dress and high heels. She sang live for us: Whitney Houston ballads, Mariah Carey, Toni Braxton. She really was a good singer. She looked amazing.”

He continued, “She was like, 15 years old. And we kind of thought, ‘Wow, this is really left of center. There’s no female pop artist out there right now.’” He realized he had basically just struck gold.

She was destined to be the new Whitney

John Seabrook remembered to Entertainment Weekly, “Clive Calder — who was the head of Jive — signed her to a provisional contract. This was a very significant moment in pop history: the signing of Britney Spears as a sort of girl-next-door teenager – rather than as a Whitney Houston-esque diva.”

“One of the calculations there was, Clive Calder was notoriously cheap, and Whitney Houston was notoriously expensive,” Seabrook said. “So Britney Spears seemed like she would be cheap too, because she was just a teenager from Louisiana, and wasn't demanding in any way.”

"Very quiet and very shy"

Jive hired Swedish producer Max Martin to create a song for their potential new star. He remembered meeting Spears for the first time in the Entertainment Weekly piece, saying, “She was 16. She thought I was a 50-year-old producer from the old school.”

“I had really long hair at the time — I looked like Ozzy Osbourne,” he continued. “It was pretty obvious that she had something, even though she was very quiet and very shy.”

A meeting of minds

Spears liked Martin upon meeting him as well. In 2018 she told The Guardian newspaper, "I was pretty young at the time, so I was nervous, but he was so nice and put me right at ease." She went on, "I think Max [Martin] is a genius. It all just came together and felt right."

"In my opinion, [he] is the greatest songwriter of all time." He is the man behind "… Baby One More Time," after all.

The man behind the myth

But how exactly did the endlessly-catchy teenage tune come to be? Martin told Entertainment Weekly, “I came up with the melody first. I wrote the chorus; you just hum it in. Thanks to [my co-producer, Rami Yacoub], that song sounds the way it does.”

“He is much more urban and R&B than me. I’m more of a melody man,” he explained. “So, he’s a big reason that the song turned out the way that it did.”

It wasn't supposed to be for Britney

But did you know that the song wasn’t even intended for Spears at first? Weiss remembered, “[Executive] Martin Dodd had this demo, which was then called ‘Hit Me Baby One More Time,’ and he sent it into us.”

Weiss recalled that Dodd said, “This is a song Max had written for TLC, but they didn’t really want to cut the record.” He went on, “When the song came into us, we thought, let’s cut this with [Spears].”

A grown-up song for a new generation

A backup vocalist named NaNa Hedin also spoke to Entertainment Weekly. She said, “I remember that I thought the song was for teenagers but the production was filled with a grown-up attitude and with sounds that I really liked.”

She continued, “I was so impressed by how a guy like [Martin] and the other writers could write lyrics that got into the hearts and spoke to teenage thinking.” But what did those lyrics actually mean?

TLC didn't want to sing it

Of course, despite the title change, the bit of the song everyone remembers goes, “Hit me baby one more time.” TLC — the group the song was originally supposed to go to – was reportedly dubious about that lyric, too.

Tionne “T-Boz” Watkins was asked about it back in 2013. Asked by MTV News what she thought of the song she passed on, T-Boz answered, “I was like, I like the song but do I think it’s a hit?”

"I’m not saying ‘hit me baby’"

T-Boz continued, “Do I think it’s TLC? I’m not saying ‘hit me baby.’ No disrespect to [Spears], it’s good for her. But was I going to say ‘hit me baby one more time’? Hell no!”

“Every song isn't good for each artist, and when you're a real artist you know what you believe in and what you really want to sing,” T-Boz explained. “So, I'm clear that it was a hit, but I'm also clear that it wasn't for TLC.”

Simon Cowell almost poached the song

“… Baby One More Time” very nearly got sold to Cowell before it ended up with Spears. The mega-producer was managing the band Five at the time, and he thought it would be the perfect track to break them in the U.S. He told the Howie Mandel Does Stuff podcast how he begged for the song.

“And I said, 'Max, let me give you some advice, no one is going to have a hit with the name Britney Spears.' She wasn't even known.” But we know how that turned out, don't we?

Nobody got it

The “hit me” part of the song also apparently caused trouble, because it was constantly misinterpreted — and we can see why. Seabrook remembered to Entertainment Weekly, “Before the song came out, nobody in America liked the hook, ‘Hit me baby one more time.’”

The creatives behind the song claim there was one simple reason for that: the language barrier between Sweden and America. “Everybody thought it was some sort of weird allusion to domestic violence or something,” Seabrook said.

Something was lost in translation

Seabrook explained, “What it really was was the Swedes using English not exactly correctly. What they really wanted to say was, ‘Hit me up on the phone one more time’ or something. But at that point, [Martin’s] English wasn’t that great,” Seabrook claimed.

“So it came out sounding a little bit weird in English. But when they tried to get him to change it, he said, ‘No, it can’t be changed. That’s it.’”

The "hit me" was dropped

Barry Weiss told Entertainment Weekly, “I actually changed the lyric. I was concerned about going to U.S. radio with a song called ‘Hit Me Baby One More Time.’” He probably wasn’t alone in this concern, either. That's how the production team came up with the brand new title.

“I don’t know if I’m proud of this or not: I came up with the ‘… Baby One More Time,’” Weiss explained. But even today not everyone knows for sure what the lyric means.

Does it make sense?

The song turned 20 years old in October 2018, and Cosmopolitan magazine ran a headline asking, “Just checking: do you know what ‘... Baby One More Time’ is really about?” As it turns out, most people are still in the dark when it comes to the song's true meaning.

The article itself said, “The song — which turns 20 this week — is a beautiful hodgepodge of three piano notes, bubblegum pop goodness, and lyrics that still don’t make sense to this day.” But Spears has gone on the record to set people straight.

Britney speaks

When Spears appeared in Rolling Stone in 1999, the meaning of the lyrics to "Baby" came up. "It doesn't mean physically hit me," she said. "It means just give me a sign, basically. I think it's kind of funny that people would actually think that's what it meant," Spears claimed at the time.

But then Spears also revealed that she did ask Martin to change the lyrics to another song, "Born to Make You Happy." She apparently thought the original version was too "sexual."

The video made it worse

Even if people don’t understand the “hit me” part of the song, they probably remember the music video. The making of it — and Spears’ role in that — also came up in the Entertainment Weekly piece.

It was originally supposed to be something very different from how it ended up. In fact, the first pitch for the video made it sound suspiciously like the eventual video for "Oops!... I Did It Again."

It could have been very different

Barry Weiss told Entertainment Weekly, “Nigel [Dick, the director] came up with an idea, like, [Spears] is in outer space. She comes and lands on Mars on a spaceship, and then she breaks into this dance routine.”

But Spears herself hated the idea and said, “This is horrible. No way am I doing this. This is really cheesy.” Although she obviously didn't hate it enough to dismiss it for a future single.

The video took on a life of its own

According to Dick, the whole school theme of the video was Spears’ idea. He told Entertainment Weekly, "Your initial reaction to this is, I’m being told by a 16-year-old girl what I should do...[But] this girl is 16 and I’m a grown man; perhaps she has a better perspective on her audience than I do."

"So, I swallowed my pride," Dick said. Given the song and music video's instant popularity, it was the right call. The resulting video would create waves for its own reasons.

"Wouldn’t I wear a schoolgirl outfit?"

Speaking to MTV back in 2009, Dick said, “My idea originally was just jeans and T-shirts, and we were at the wardrobe fitting and Britney holds up the jeans and T-shirts and says, ‘Wouldn’t I wear a schoolgirl outfit?’” Good point! “Every piece of wardrobe in the video came from Kmart, and I was told at the time [that] not one piece of clothing in the video cost more than $17,” Dick explained.

“On that level, it’s real. That probably, in retrospect, is a part of its charm.”

It caused a bit of a scandal

That 1999 Rolling Stone cover story described the video for "Baby" as showing a "17-year-old singer cavorting around like the naughtiest of schoolgirls." But Spears was quick to note that there was nothing revealing in the actual video. "All I did was tie up my shirt!" she said.

"I'm wearing a sports bra under it. Sure, I'm wearing thigh-highs, but kids wear those — it's the style. Have you seen MTV — all those girls in thongs?" She definitely had a point.

Music history was made

The rest, of course, is music history. As soon as the song was released, good reviews came flooding in. Billboard wrote “‘...Baby One More Time’ chugs with an insinuating faux-funk beat and super-shiny synths. Spears has a charming kewpie-doll voice that has a soulful quality.”

The song quickly went platinum, and Spears picked up several awards off the back of its success. At the 1999 MTV Europe Awards she won not only Best Song, but also Best Female, Best Pop, and Best Breakthrough Artist. She also performed the song at the 2000 Grammys.

The greatest debut single in music history

Such is the legacy of “… Baby One More Time” that in 2020 Rolling Stone named it the greatest debut single in music history. The famous publication said that it was “one of those pop manifestos that announces a new sound, a new era, a new century. But most of all, a new star.”

The article went on to say that the tune “is an apocalyptic thunderclap of a song, with Max Martin’s mega-boom production. The only detail he screwed up was the incredibly annoying ellipsis in the title.”

Britney is definitely a fan

Spears told Rolling Stone in 2000 that her inspiration for the vocals was Softcell's “Tainted Love,” which she described as “a sexy song.” She said, “I wanted my voice to be kind of rusty. I wanted my voice to just be able to groove with the track.”

“So much attitude in that song,” Spears beamed. “I was so happy because there’s a lot of good songs out there, but it’s rare when you can take a song and really put your name all over it and put your personality into it.”

A drain on her mental health

Spears was poised to become the biggest star in the world. Her first two albums, ...Baby One More Time (1999) and Oops!... I Did It Again (2000), are still two of the best-selling albums in music history.

But Spears was still only a teenager when those albums dropped. Many people must have wondered what kind of career Spears had ahead of her. And as it turned out, Spears began to experience the same drain on her mental health faced by many young superstars.

The music speaks for itself

Even though Spears didn’t write all of her most popular songs, many of them still seem to reference the troubles she was having in her life. When you look back on them, some lyrics could be foreshadowing what was to come.

For instance, 2000’s “Lucky” is all about a superstar wondering, “If there’s nothing missing in my life, then why do these tears come at night?” It’s hard to hear this now and not think of later years in Spears’ life.

Singing about breakdowns

And 2004’s “Mona Lisa” — which Spears co-wrote with lyricists David Kochanski and Teddy Campbell — hints at an unhappy state of mind as well. She was starting to shed her bubblegum-pop image at that point and aim for a more grownup market.

This song was included on an EP to complement the release of her short-lived reality show, Britney & Kevin: Chaotic. In “Mona Lisa,” Spears sings, “Everyone’s watching as she starts to fall, they want her to break down.”

Britney and Justin: the original power couple

This was something Spears likely knew something about. The media spotlight she was under in the early 2000s was intense. Her relationship and subsequent breakup with Justin Timberlake made headlines — and not always good ones.

After the split, Timberlake released the famous video for his song “Cry Me a River.” Everyone knew it was really about Spears — and the field even featured a Spears lookalike. Spears reportedly wrote “Everytime” in retaliation.

A "chaotic" lifestyle

After leaving Timberlake, Spears married her childhood friend Jason Allen Alexander... for 55 hours. That's how long the annulment took to come through! The media had a field day with that one, of course, but Spears quickly found a new love in Kevin Federline.

They also got married quickly, but they remained together for three years. The couple had two children, but Spears filed for divorce after the birth of their second kid. Unfortunately, around that point, the media began to hone in on her seemingly erratic behavior.

Framing Britney

It’s very well documented what happened next. In 2007 Spears had a very public breakdown, and she ended up being sent to psychiatric hospitals twice the following year. There was the infamous incident when she shaved her head.

Sadly, the media reaction was far from sympathetic. Jumping back to the lyrics of “Lucky,” members in the press seemed to suggest that Spears really wasn’t supposed to have anything missing from her life.

Losing everything

Spears lost custody of her children to Federline in October 2007. And at the end of 2008, Spears’ father, Jamie, was granted a conservatorship over her. That meant she could no longer make legal decisions about her own money. Instead, the singer’s father and attorney Andrew Wallet would do so.

Eyebrows were raised at the time since conservatorships are usually used for those with severe disabilities. Los Angeles Superior Court Commissioner Riva Goetz said, "The conservatorship is necessary and appropriate for the complexity of financial and business entities and her being susceptible to undue influence."

The conservatorship finally came to an end

Interestingly, the conservatorship only came to an end in 2021 — 13 years after it was first put in place. But ever since the era of “… Baby One More Time,” Spears has had a vast army of fans on her side.

Concern about the conservatorship would eventually grow into a whole movement called #FreeBritney. There were documentaries about the issue, and other celebrity fans and peers including Miley Cyrus and Cher expressed support.