Spears compared her time at school to Clueless in a 1999 interview with Rolling Stone: “I was so bored. I was the point guard on the basketball team. I had my boyfriend, and I went to homecoming and Christmas formal. But I wanted more.”
This photo is certainly one of her oldest photos. Was she even old enough to drive that truck? Maybe but she doesn't look it.
Spears and Timberlake’s 3-year relationship had the world head over heels until their heartbreaking split in 2002. Not to mention the “he said, she said” that sent paparazzi on an anti-Britney rampage.
Apparently, Timberlake was also in his denim cowboy phase at the time this photo was taken. It's good he dropped the look in favor of something chicer.
It’s easy to forget that Spears was a small town girl who was equally as fascinated with “big city” life as the rest of us.
This harkens back to a time when Britney was very much innocent and before the "big city" changed her life, and in some ways, ruined it.
During free time between MMC and before ...Baby One More Time, Spears was studious and active in basketball at her Mississippi school Parklane Academy.
Had her music career taken off, would she have become a famous basketball player? Who is to say? But we are glad the music thing worked out nonetheless.
Before each singer’s lucrative careers, Spears and Christina Aguilera starred on MMC as Mickey’s famous Mouseketeers.
Awww, to be young and not competing with each other on the music charts. Disney really does bring people together and is certainly good at picking out talent.
Britney’s role as an MMC Mouseketeer might not have lasted for long, but it was a step in the right direction for the young star.
Besides Christina Aguilera, other famous Mouseketeers included Justin Timberlake, Ryan Gosling, and JC Chasez. Oh, what a club to have been in as a kid!
Felicia Culotta, a long-time friend of the Spears family, spoke about her time as Spears’s assistant in New York Times' “Framing Britney Spears.” “For a long time they called me her chaperone, and then at one point they wanted to call me her partner, and we didn’t think that sounded right. I definitely was not her mother, and I wasn’t her big sister, so we settled on assistant.”
Felicia Culotta, who was also an assistant for the Jonas Brothers, is now an artist and producer for & Juliet, a musical take on the story of Romeo and Juliet which takes place in an alternate universe in which Juliet doesn't die at the end of the story. It features the music of Swedish pop writer Max Marin.
Hype surrounding her debut album ...Baby One More Time began with a shopping mall promotional tour, which led her to eventually star as the opening act for NSYNC.
Her debut single, written by Max Marin, ended up topping the charts in a whopping 22 countries, including the United Kingdom where it is triple-platinum certified.
With the release of her second single “Lucky" about a suffering Hollywood starlet, it’s a surprise that no one saw her imminent fight for freedom from paparazzi and conservatorships coming!
She definitely wasn't feeling lucky when the courts got involved in her life but we are sure her family probably did. As for the song, it was the second single from her second studio album that topped the charts in Austria, Germany, Sweden, and Switzerland.
Spears’s second studio album Oops!... I Did It Again skyrocketed the 2000s charts and has sold over 20 million albums since its release.
The album received mostly positive reviews from critics and it debuted at number one on the Billboard 200 charts. It had a first-week sales record of 1.39 million copies sold.
What about this shot in front of the Eiffel Tower? Here, Spears looks like the young and independent woman she always strives to be.
Ah, being famous always means you get to go to new and interesting places at a very young age but it's also never a private affair...so there's that disadvantage.
In 2001, Spears performed as the opening act to Aerosmith and NSYNC for Super Bowl XXXV’s halftime show. An $8 million promotional deal with Pepsi came swiftly after.
If there were two things you could guarantee would draw in audiences at the time, you can be sure that it was football and Britney!
Spears wasn’t a one-dimensional puppet of Hollywood management but made her own decisions on what she wore, sang, starred in, and promoted. Take Crossroads, a 2002 acting stint that might not have impressed critics yet highlighted her multitalented qualities for fans.
Crossroads was released in 2002 and also starred Zoe Saldaña and Anson Mount, who would become stars themselves. Both of them have roles in the Marvel Cinematic Universe), as well as Dan Akroyd and Kim Cattrall. The movie had a budget of $12 million and earned over $60 million at the box office.
The 11-year-old Britney Spears’s first acting stint was for Disney’s The All-New Mickey Mouse Club (MMC). Alongside Justin Timberlake and Ryan Gosling, Spears blew away the studio audience with her impressive vocals.
Indeed, the House of Mouse was the ideal place for young stars to find their footing in the world of celebrity. Not all of them were lucky, but we certainly got some of the best.
Besties for the restie, Justin Timberlake, Ryan Gosling, and Britney Spears were a Mickey-approved trio since their days on MMC that revved fans up for the infamous coupling of Spears and Timberlake.
Of course, while they have all tried their hand at acting, it's Gosling who took off in that arena, while Britney stayed in the music scene. Timberlake, however, has done a good job balancing the two.
Spears melded personas of innocence and liberation, with many fans pointing to her iconic 2003 MTV Video Music Awards performance where she and Christina Aguilera had a moment during Madonna's song.
For Generation Xers, Madonna was the pop icon of their time. But for millennials, it would have to be Britney. The bringing of her onstage with Madonna was just to be expected.
Spears’s 2004 engagement to Kevin Federline switched gears into a fast-track L.A. wedding that sent the media raging. At least Britney had one day to be completely happy before more tabloid lies about her life.
The media definitely had their issues with Kevin Federline since he wasn't quite a man of talent himself. The mix of them together left people really scratching their heads, but it's important to remember that sometimes opposites just attract.
Sibling Jamie Lynn Spears might be Britney’s little sister, but she doesn’t pout about living in the shadow of the “Princess of Pop.” Instead, she went on to star as the main character for Zoey 101 and get into her own tabloid scandals.
Admittedly, we sometimes forget Jaime Lynn even exists. Where is she now, and what is she doing? We don't mean to pick on her though, because even with all the bad press following Britney, she still ended up living in her sister's shadow, and that's gotta be rough.
Because Spears isn't on the top of the Billboard charts doesn’t mean she isn’t the focus of tabloid slander. It’s natural to keep up with what’s being said about you, but taking it in moderation is important for mental health.
There's really no saying how large of a role the media ended up playing in ruining her life, ultimately leading to her conservatorship. As they aimed to paint her as insane, it undoubtedly had some impact. But that being said, at least they did their part in giving her her life back because, hey, everybody loves a redemption arc!
Britney definitely tried to bring it during the 2007 MTV Video Music Awards when she performed "Gimme More" on stage that year. It was a performance that caused the talk of the town, to say the least.
Critics of the performance felt it was quite lackluster and that Britney was not at the top of her game. Some might even say she looked downright confused.
