Very few pop stars are as iconic as Britney Spears. She’s a woman who started out looking very innocent, but as we got to know her, discovered that she was anything but. She’s made some epic blunders on the world stage, but more often than not, Britney Spears has done some amazing things. She grew up in the public eye, coming to prominence as a teenager and working out the person she was going to become with the whole world watching. That’s enough to make anyone crack under the pressure. While she ended up cracking under the pressure of fame several years ago, she staged a major comeback and is still one of the most famous and best-selling pop acts on the planet.
We decided to take a bit of a walk through her career, focusing in on twenty moments that were memorable in her career and her life. Some of these moments are milestones in her career that we still sing along to nearly twenty years later. Others are darker moments in her personal life that dominated the news and made us wonder if she was going to be another casualty of fame. Still, others are funny moments that haven’t had an impact on her life today, but still, make us wonder what on earth she was thinking. All in all, she’s become a really interesting person, and no matter what you think of her music, you have to admit that she’s a person who deserves respect. Here are twenty photos that represent twenty milestones in Britney Spears’ life and career.
20. Baby One More Time
Before this song and music video, the world had never heard of Britney Spears. However, the day this video dropped, advertising Britney’s sound and aesthetic, the world kind of exploded. She basically took the schoolgirl look and sexualized it, putting forth this idea that she was innocent, but not really innocent. This made her kid friendly and the subject of fascination for adults. This video was the source of a bit of controversy when it came out in the nineties, but if you look at what people are doing in music videos in 2017, this video is pretty tame. This video is actually pretty tame in comparison to what Britney Spears is doing now, nearly twenty years after this song came out.
19. The Matching Outfits With Justin Timberlake
We’ve all done some cringeworthy things with a significant other. Some of us take ridiculous amounts of selfies with our significant others. Others post every aspect of their relationships, no matter how ill-advised doing that is. However, some celebrities take it to a place that makes it really awkward to look at the photos 20 years later: matching outfits. Britney Spears did this a few times with then-boyfriend Justin Timberlake, but the outfits they chose did not age well. One time they did this that showed just how tacky these two superstars could be together was the jean ensemble they wore. Even as a kid, I knew that this was not one of their better decisions. This was also something that happened not long before the end of that relationship, so this jean ensemble could even be seen as a cry for help. The lesson to take away from this, kids? Don’t get matching outfits with your significant other, because you might never get to live those photos down.
18. Oops I Did It Again
Britney Spears has had a lot of iconic looks. She actually had a lot of iconic looks in the video in question, Oops I Did It Again. However, the most iconic look of this video would have to be the red latex suit with the high ponytail. This look wasn’t overtly sexual, like a lot of her looks were after this, but it did show that she was willing to shed the All American “Baby One More Time” image that she’d come in on. This was also an interesting video because while the lyrics were all about making a guy believe she was into them when she wasn’t, the video was basically about space. There was also a reference to Titanic in there. It has been speculated that this song was about Justin Timberlake and their breakup, which makes sense considering that “Cry Me A River” is basically all about his relationship with Britney Spears. They’ve had relationships since then, but for many of us, this was the first celebrity power couple that really meant something to us.
17. That Time She Tried To Be Marilyn Monroe
Images like this one show us the beginning of Britney Spears’ journey from innocent looking All American pop star to the pop princess she eventually became. The comparison to Marilyn Monroe is especially apt when you consider their voices. Marilyn Monroe was famous for her breathy, high pitched voice, to the point where she used to spend hours perfecting that voice. Britney Spears does something similar with her voice when she sings. Her speaking voice also has this effect, but not nearly as much as her singing voice. The amount that she actually does it seems to vary with every album, too. Her earlier songs had this quality in spades, but as she got older and her music got more mature, this effect would largely drop away. One good example of a song where the breathiness of her voice is practically non-existent is “Everytime,” a very slow ballad. While her voice still remained high, it seemed a lot more natural and not like an effect she was putting on.
16. The Iconic Sparkly Nude Outfit
This outfit was so iconic, it was recreated for the Britney Spears episode of Glee. She wore this during her music video for “Toxic,” and she really was naked under the outfit. According to an MTV report, she had big plans for this video and went to the director of the music video with a fully formed idea in her head. “She said she wanted to join the mile-high club and be a stewardess that makes out with someone in the bathroom,” said the video’s director, Joseph Kahn. “My contribution was to make him a fat guy, because you know at some point in her videos she’ll make out with hot guys. Picking out the every-guy is a fantasy on one level for her, but you put a chubby guy in there and the common man gets something too.” He believes that her involvement in the “Toxic” video highlights her sense of humor, which is one of her more unsung qualities. “That’s just her naked with diamonds on,” he told MTV. “I’m not sure what I was thinking about when she told me about that scene, maybe those intros to James Bond movies, but every video needs an iconic image to remember, and that’s it.”
Crossroads was Britney’s first real foray into acting, and while the movie wasn’t especially well received by critics, it is a milestone in her career and kind of a cult classic. Also, this movie has a ton of people involved in it that are A-listers now. For example, the screenplay was written by Shonda Rhimes of Scandal and Grey’s Anatomy fame. Britney’s two friends were played by Taryn Manning and Zoe Saldana, names that we all know now. Basically, this is a movie where the woman behind Olivia Pope and Meredith Grey wrote a story about Britney Spears, Pennsatucky from Orange Is The New Black, and Gamora from Guardians of the Galaxy going on a road trip and harnessing the power of friendship and sisterhood. Dan Ackroyd, Kim Cattrall and Justin Long are also in this movie, too. It’s a great movie that’s highly underrated if you’re a person who goes for this type of movie.
14. We Will Rock You With Beyonce And Pink
This collaboration on a cover of Queen was amazing. Basically, it showed three princesses of pop doing what they do best. To make matters even cooler, the music video made them gladiators, showing that these are women who aren’t just beautiful, but strong as well. Not only that, but they regularly top the charts, showing others how to make a hit song. They have totally different sounds, but that actually worked well here. The song was an advertisement for Pepsi, as was the video, but this video was awesome enough that I’d actually be okay with Pepsi doing things like this more often. While I’m pretty sure Britney, Beyonce, and Pink are a bit beyond stunts like this, I would love to see more female pop stars collaborating on things like this just to show that they’re supporting each other. If Pepsi can hear me right now, I’d suggest Taylor Swift, Ariana Grande, and Halsey for a modernized version of this. It would be strange at first, but I think it could really work out.
13. The Leather Military Cap Disaster
Britney Spears has made some fashion faux-pas over the years, and this leather ensemble was definitely one of them. I still don’t understand how a person can get an outfit made of entirely leather on their bodies, to be quite honest. Leather is one of those things that either works or it doesn’t. Personally, I think the issue with this outfit is that it’s too much of one thing. The reason why leather works in combination with other fabrics like lace is that the leather serves to give it that extra edge. When you end up wearing all leather, it just looks like you’re trying too hard, which normally isn’t something I’d ever say about Britney Spears. The shoes she’s wearing also don’t really do her justice, either.
12. The Snake
This is one of Britney’s most iconic looks, just because it was so out of left field. Everything about it was different from what she’d done before that. Sure, she’d had some provocative looks before this, but this was the point where the world had to come to terms with the fact that Britney Spears was a woman now. As a kid watching this, I remember being struck by the fact that she was holding a snake, especially since I was terrified of snakes at the time. It might warm your heart to know that as of last year, that snake was still alive! A Vanity Fair article detailed the journey to tracking down the albino Burmese snake and they found her alive and well. She didn’t have a name when she came to fame on Britney’s shoulders, but the author named her Banana. According to the trainer, she weighs 100 pounds now and measures up to 14 feet long.
11. The Kiss With Madonna
The performance with Christina Aguilera and Madonna was a great one, but the performance itself gets overshadowed by the kiss that shocked the world at the time: the one with Madonna and Britney Spears. This kiss would be considered tame if it had happened now, but for 2003 this was a really big deal. It was actually called “the kiss hear around the world.” While Christina Aguilera also kissed Madonna and was also known for a more clean cut and innocent looking act, it was Britney Spears that made the news because she hadn’t made the complete transition from teen pop star to sex symbol the way Christina Aguilera did. Around the time this happened, Christina had come out with Stripped, a huge departure from her earlier sound. Either way, this was one of the big moments of Britney’s career.
10. Britney And Kevin: Chaotic
Britney and Kevin: Chaotic was one of the many reality shows that came out about pop stars just living their lives. However, this one was unique because it showed the beginning of Britney’s descent into a really dark place. She’s called it the worst career move she’s ever made, and she’s right. The camera work was terrible in every single episode, and they made her look crazy for no reason. It was like the producers of the show made it a point to consistently make Britney look worse than she actually was. On top of that, the show was way more personal than it needed to be with all of the times Britney was showing off to Kevin. To make matters worse, Kevin was clearly trying to capitalize on his newfound fame, and it showed in the worst possible way.
9. Kevin Federline’s Album
We need to take a moment to talk about Kevin Federline’s album because this was also a moment in Britney Spears’ life as well. She was plugging for this album as much as he was, going so far as to say that he had “flow.” I was a teenager when this album came out, and I was curious, so I found myself listening to this album at 2 AM, trying to figure out if Playing With Fire was really as terrible as everyone said. Not only was it as terrible as everyone said, people were actually under-reacting to it. I’m sure a lot of us forgot about this album, but that’s probably because your brain blocked it out. I spent the entire time listening to it laughing, and I remember that so clearly because that experience taught me that there is such a thing as terrible music. That realization was a formative one for me, and I’m sure others had the same experience.
8. The Walk Of Fame Star
Britney Spars was one of the youngest people to be awarded a walk of fame star. She earned it in 2003 at the age of 21, making her the youngest person to earn one because she was the same age that Melissa Gilbert of Little House on the Prairie fame was when she got hers in 1985. Britney getting her star was heavily covered in the media. “I’m seriously speechless right now,” Spears told the crowd according to CBS. “This is something that I’ve dreamt about since I was a little girl. I can’t believe I’m actually here with all of you amazing fans.” She spent the whole time signing posters and talking to fans, showing that she actually does care about her fans. That’s a quality that hasn’t changed about her.
7. The Flight Attendant
This is one of the looks that came from her “Toxic” video. Because Britney was so involved with this video, we can see that she not only has a good sense of humor but that she’s very well aware of why she’s so appealing to the general public. For example, there’s this one scene in the video where she spills water on a guy, provocatively cleans him up, and then goes to kiss the head of a child. “That’s part of her brilliance,” Kahn said. “She has this weird awareness of her appeal. She totally understands that she’s naughty and nice, that she’s the girl next door gone bad who is constantly titillating you. She’s not like most artists who flaunt their pure sexuality. She toys with you and leaves you conflicted.”
While this period in Britney’s life counts among the most turbulent years for her, this album was among her best and most underrated. While she’d long since shed her image as an innocent schoolgirl saving herself for marriage, this album kind of pushed the envelope a bit more. This album was also overshadowed by the turmoil in her personal life. Around the time this album came out, she was getting divorced from Kevin Federline and dealing with mental illness. While this album received mixed reviews from critics, it has the most consistent sound out of all of her albums up to that point. Unfortunately, people don’t remember the music from this time in Britney’s life. They remember the widely criticized VMA performance of “Gimme More” and several instances of behavior that was very out of character for her.
5. The Shaved Head
When we think about Britney Spears’ widely publicized mental health breakdown in 2007, the first thing we think of is probably her shaved head. We’re still talking about it ten years later, even though she’s long since recovered from this. Unfortunately for Britney, this instance wasn’t even the thing that illustrated her long, slow journey to rock bottom. This is just the instance that’s really stuck out in the public consciousness. Some people took inspiration from it to the point “If Britney Spears can make it through 2007, you can make it through today” has achieved memetic status.
Others tried to ascribe meaning to it, with varying levels of success. “She seemed to be trying, with befuddled brilliance, to tell the truth. She recoiled from celebrity culture by mortifying her own flesh. She stripped herself, publicly, of her sexuality. She presented herself as a grotesque,” Mark Stevens wrote in New York Magazine months after the incident. “Few gestures are as symbolically rich as the shaving of a head. That’s what monastics do when they reject the flesh to dedicate themselves to the spirit. In boot camp, soldiers lose their individuality with their hair. Delilah cut off Samson’s to make him defenseless.” While that might seem like he’s trying too hard to make a point, there’s something to be said for this.
If Blackout was Britney’s darkest album, Circus was an indicator that Britney Spears was coming back. While her brighter, poppier sound was definitely back in full force on this album, complete with singles like “Womanizer” that burrow themselves into a person’s head and never leave. “Womanizer” is also a great example of Britney’s sense of humor, which has been brought up a few times before. This was also an album that showed off songs that were dedicated to her children, to the paparazzi always tailing her, even to some of her psychological issues. This was also the first album in awhile where she had a real ballad, which is saying something since slower songs are a rare thing for Britney. This era in her career showed that even after several years, she has the ability to keep the world guessing.
3. That Time She Was On Glee
Britney Spears has had some strange acting work. However, the most interesting thing she’s probably done in awhile is her stint on Glee. In it, she was basically a fantasy figure of…herself, inspiring the kids to perform covers of her songs under the influence of laughing gas they got from the dentist. The episode ended with a “Toxic” cover in the style of Bob Fosse that ended in a “Britney Spears Sex Riot.” The show had major issues over the course of its six-year run, and their second Britney Spears-themed episode had major issues because of the way it handled her fall from grace and subsequent comeback, but the season 2 episode “Britney/Brittany” did a great job of conveying what makes Britney Spears awesome: her ability to straddle the line between sex symbol and more traditional role model. If anything, she’s spent her career playing jump rope with that line.
2. Sean And Jayden
While Britney Spears has made an incredible career for herself, her biggest source of pride has to be her two sons with ex-husband Kevin Federline: Sean Preston and Jayden James. Last year, she celebrated their birthdays with a dual birthday party with a Pokemon theme. She even spelled out “Happy Birthday” in balloons over the family pool. She’s made it a point to keep her kids out of the news cycle, but they’re on her social media accounts like Instagram, showing up every once in awhile. They’ve even stolen her phone to prank her before, with hilarious results. The kids were born within a year of each other, making them Irish twins. Sean’s birthday is on September 14th, 2005, while Jayden’s is on September 12th, 2006. While Britney’s mental health hasn’t always been the best and she even lost custody of her sons for awhile, she’s always seemed to love being a mother. “[Motherhood] has taught me how to put others’ needs ahead of my own. My sons are my most precious gift, and I always want to do right by them,” she told Vegas Player magazine in November.
1. Looking Better Than Us At 35
Like many celebrities, Britney Spears has many social media accounts where fans can follow her to get a glimpse into her day to day life. While many celebrities are great at social media, Britney Spears has been making the news recently for her Instagram photos, where she’s showing off her toned body. She’s very quickly becoming fitness goals for all of Instagram with some of her newest photos. On top of that, she’s actually fit: one Instagram post has her literally standing on her boyfriend’s shoulders, while another shows her actually working out at the gym to the song “Fergalicious” which is something every woman has done at the gym at least once. She might even be more toned now than she was at any point before this. She’s even casually shown up other stars who’ve tried coming for her, like Katy Perry. While there are other moments in Britney’s career that are important, these moments are a good example of the ups and downs of her life, and how she’s overcome a ton of adversity to get to a better place.