16 Most Iconic Pics Of Britney Spears Ever Captured

Britney Spears has had one of the most iconic and enduring careers in recent music history. For nearly twenty years, Britney had entertained, fascinated, and confused not just her fans, but the entire world.

When "… Baby One More Time" was released in 1998, Britney was only 16 years old. Yes, 16 YEARS OLD. And yet, she immediately became one of the most recognizable faces and bodies in the world. At this point, Britney's image mixed sweet and sultry together. She was a daydreaming schoolgirl, then an alien princess wearing a red latex jumpsuit. However, Britney grew up in front of the world and indulged in more sultry looks with her music videos for “I'm A Slave 4 U” and “Toxic.” And then 2007 happened.

2007 was the year of the first iPhone, Grey's Anatomy mania, and Britney Spears' now iconic breakdown. In retrospect, Britney's breakdown was just a natural response to the pressure, stress, and attention put on such a young woman, who had no real agency for herself. It's now 2018 and most celebrities will turn to their social media accounts in order to engage their fans. Does that celebrity want to correct a press story or promote their newest film? They post to Instagram. However, Britney was without Instagram, so many of the most scandalous photos of her time were taken by the paparazzi catching her at her worst moment, with Britney unable to tell fans the real story.

And so, below we have the 16 most scandalous Britney Spears photos of all time. Surprisingly, they aren't all from 2007. Britney has been scandalous in some way, shape, or form since 1998. If Britney does it, people are talking about it. But that's just the charm or Britney.

16 This Spread Of Britney In Rolling Stone Was So Hot It Led To A Literal Boycott

Let's travel back to a simpler time: 1999. It was a time in which Britney was the single most adorable and single hottest woman on the planet. And yes, she was also only 17 years old. But hey, this was all Britney's brand. It mixed her innocent, energetic youthfulness with her in-your-face sensuality. There is no better example of this dichotomy than Rolling Stone's 1999 photoshoot of Britney Spears.

The 1999 Rolling Stone cover featured Britney talking on a telephone, holding a Teletubby, and with her shirt completely open to expose her black bra. The spread also featured photos of Britney in her hometown, including the above. It was 100% the Britney Spears of the time, as she was the innocent seductress. The American Family Association was so disturbed by the mixture of childhood innocence and adult sensuality that they literally called for a Britney Spears boycott. Yes, Britney was so hot that the AFA wanted to boycott her, as she would taint the youth of America.

Of course, no one boycotted Britney, and she went on to release hit single after hit single, but this was certainly one of the first big scandals in Britney's career.

15 The World Was Simply Not Ready For This Friendship

Many of us forget about this glorious friendship, but Britney Spears and Paris Hilton were BFF for a short, perfect moment in time.

After filing for divorce, Britney wanted to explore her new freedom, as she had missed out on a normal life since becoming world-famous at the age of 16. At this point, Britney started going to Los Angeles clubs with Paris Hilton. During her nights out with Paris, Britney was photographed sans underwear on several occasions. Ever the good friend, there are several photos of Paris standing in front of Britney as she got herself out of a car, with Paris was acting as a literal human shield and keeping Britney from yet another up-the-skirt shot. That is friendship, y'all.

Also, rumor has it that Paris nicknamed Britney “The Animal,” as Britney would act first and think later. If I had one wish in life, it would be to go out with Paris Hilton and Britney Spears in 2006.

14 This Original Holy Trinity Of Partying

You know how I said my one wish would be to party with Paris Hilton and Britney Spears in 2006? Scratch that. I want to party with Paris Hilton, Britney Spears, and Lindsay Lohan, which may be the most iconic trio of all time.

Of course, the photos of Britney, Paris, and Lindsay out clubbing aren't necessarily scandalous in and of themselves, but they created a narrative for the media. These three women were dubbed part of that young, partying crowd in Hollywood. It helped play into the narrative that Britney Spears had spun out of control as if she didn't deserve a few nights out with her girlfriend after literal years of working every single day.

Paris Hilton's specific account of the night is kind of spectacular. As Paris said, “Actually, it was just Brit and I [going] out. And then [Lindsay] chased us to the car and got in. She wasn't invited." Poor Lindsay.

13 Britney's 55-Hour Marriage Was Announced In The Most Epic Fashion

Only months after that iconic Madonna kiss, Britney Spears got married for a whole 55 hours. While partying Las Vegas, Britney flew in Jason Alexander, her childhood friend from Louisiana. The pair reportedly watched Texas Chainsaw Massacre in her hotel suite, then decided they would get married. And yes, they certainly may be the only people to have ever decided on marriage while watching Texas Chainsaw Massacre. Though, Alexander has said that they had been drinking and indulging in “party favors,” which may explain their mindset.

After paying $70, the pair had a 7-minute ceremony and Britney was off the market for a whole 55 hours. Upon finding out about the marriage, Britney's manager arranged a record-time annulment, to which both Britney and Alexander happily agreed. By the time the media found out about the situation, the pair were annulled and all that remained was this iconic photo, in which Britney wears a garter belt around her ripped jeans.

There is reportedly a video of the wedding that Alexander was offered $1 million for, but he turned down the offer. So honestly, Britney married a pretty standup guy her first time around.

12 The Tackiest Wedding Of All Time: Britney Spears And Kevin Federline

The 55-hour marriage wasn't Britney's only relationship news in 2004. Britney started dating backup dancer Kevin Federline, all while his ex was pregnant with his son. There were accusations of Britney being a home wrecker and Federline being a gold digger. Despite the tense media scrutiny, Britney and Federline were engaged after just three months of dating. The pair married in September 2004. And yes, this is totally a real picture from their reception.

Why did Britney marry THIS GUY when she was at the height of her stardom? Well, Britney had broken up with Justin Timberlake in 2002, which was followed by her 55-hour marriage and then… Kevin Federline. One could reason that Britney was looking for someone she could depend on. Or maybe Britney wanted to rebel and Kevin Federline was the ultimate rebellion. Whatever the case, the pair filed for divorce in 2006, which many believe led to Britney's breakdown.

11 That Time Britney Kissed Madonna And The World Stopped Spinning On Its Axis

In the rise and fall of Britney, was this the moment that she switched gears? It certainly seems like that could have been the case.

At this point, Britney had long been an MTV VMAs staple. In 2000, Britney appeared on stage wearing a pantsuit, only to rip it off and dance in a nude, sequins bikini top and low-cut pants. It was the moment in which Britney told the world she was a woman and she could own her sensuality. In 2001, Britney danced with an actual python on stage and it was perhaps the hottest Britney Spears ever was. Actually, it was maybe the hottest anyone had ever been in the history of people.

At the 2003 award show, Britney outdid herself once again. This time, she sang alongside Christina Aguilera and Madonna, which culminated in a Britney and Madonna kiss that pretty much stopped the world from spinning on its axis. The camera panned to Britney's ex Justin Timberlake, who looked so very uncomfortable. This was also the moment in which Britney has shed any last "innocence." Now, Britney was a bad influence and out of control. It wouldn't be for another four years that Britney would shave her head and combat the paparazzi with an umbrella, but the cracks in Britney's perfect façade were certainly visible in media stunts such as this kiss with Madonna.

10 Even When Pregnant, Britney Refuses To Shop In The Maternity Section

Britney Spears is known for wearing half tops that show off her toned stomach and belly ring. In fact, one could make a good case for Britney Spears being the reason for belly rings' popularity in the early 2000s. So, if we're so used to seeing Britney flaunt her body normally, why were we so surprised to see Britney wearing this while pregnant? Sure, it's not your normal maternity clothing, but Britney Spears is far from normal. She's Britney freakin' Spears! Of course, this is how she's going to do maternity wear.

This was around the same time that Britney was doing things to push the envelope. She would often dress in clothing which revealed her bra and/or underwear. In one situation, paparazzi caught a barefoot Britney using a gas station restroom. Like, her bare feet were touching the floor of a public restroom. I know, it's pretty gross. Though, many see this time in which Britney was trying to prove to the world that she was not, in fact, their pop princess. Britney Spears was a swamp monster from Louisiana and she was going to prove it to us by putting her bare feet down in a public restroom.

9 Because Who Needs A Car Seat?

When the paparazzi captured this photo of Britney Spears, the world mommy shamed the hell out of her. The fact that Britney was driving with her infant son in her lap, instead of in a car seat, horrified people, as they feared for her son's safety and her inability to properly parent. In a statement, Britney explained: “I was terrified that this time the physically aggressive paparazzi would put both me and my baby in danger. I instinctively took measures to get my baby and me out of harm's way, but the paparazzi continued to stalk us. I love my child and would do anything to protect him.”

Many outraged people spoke out and asked for Britney to be held accountable by authorities, though one sheriff explained, “Unless a deputy saw the violation, there's nothing we can do. We don't even know if this took place in our jurisdiction.”

Yes, Britney driving in such a way put both her and her son at risk. Though one also has to wonder how much danger Britney and her family had been put in solely because of the paparazzi so closely following her.

8 Let Us Not Forget The Falling Baby Scandal

Yet again, the paparazzi caught Britney Spears at her worst parenting moment and the world completely misinterpreted the situation.

While leaving the Ritz-Carlton Hotel in New York, Britney was carrying Sean Preston in one hand and a drink in another hand. When a paparazzi reportedly pushed Britney, she tripped and this photo was snapped. Sean's tiny orange hat flew off and Britney's bodyguard had to step in to help. The media was quick to write stories about how Britney didn't spill her cocktail but nearly dropped her infant son. Never mind the fact that Britney reported burst into tears after securing her son. Never mind the fact that paparazzi snapped photos of the scene without stepping in to help Britney and her son. Unfortunately, the poor press and Britney's documented mental instability led to Kevin Federline retaining sole legal and physical custody of their children, while Britney received visitation rights.

Also, this is not to say Britney Spears was Mother of the Year. She was flawed, just as the rest of us are. Unfortunately for Britney, all of her flaws and worst moments were broadcast to the entire world.

7 But Britney Said She Doesn't Know Taylor Swift?

This photo feels like the most wholesome photo ever taken, but there's a bit of scandal tucked in here.

In an interview, Britney was asked if she'd rather sit next to Katy Perry or Taylor Swift on a flight. Britney answered, “I don't know! I don't know, that's hard. They're both so cool, I don't know. I've briefly met Katy Perry at the Smurfs movie premiere. Maybe because I've met Katy Perry, I would say Taylor Swift, because I've never met her before.”

Fans found this photo of Britney's crimped hair and Taylor's country curls together from the 2008 VMAs, which is proof that Britney actually did meet Taylor. So, did Britney forget about meeting the curly-haired country princess or was this a subtle slam? Just kidding, Britney literally never slams anyone. It's likely Britney simply forgot meeting Taylor, because Britney's mega famous and meets a lot of people.

6 It's Not Photoshopped, Britney Is Just THAT Hot

What could possibly be scandalous about this photo of Britney's super toned body? Well, many assumed it was photoshopped. Critics of the photo point to the area underneath the arch of Britney's stomach, arguing that we should see tiles or cement there rather than water. Plus, Britney's body looked too good. I mean, we've seen the pop princess go from her ripped “I'm A Slave 4 U” body to, well, less than perfect. Since 2007, we hadn't seen Britney looking this good, so critics assumed it was photoshopped.

While the photo caused some major questions, it seems this photo actually wasn't photoshopped at all and Britney is honestly just that good looking. Britney didn't respond to the speculation. Instead, she simply posted a video of herself in a bikini, y'know since you can't photoshop a video. The video footage of Britney put the haters to rest, as they could no longer argue that Britney wasn't in the best shape of her life.

With a career spanning over two decades, photos of Britney have been scandalous for multiple reasons, from her breakdown to her not knowing Taylor Swift to her sex appeal. What remained at the center is that we cannot stop talking about Britney, whether she's bald and swinging an umbrella or rocking a head full of hair and lounging by the pool.

5 Once Upon A Time, The Biggest Britney Scandal Was This Python

It's been 20 years since Britney Spears entered the public eye. We've all been through a lot with Britney - all her ups and all her downs… and downs, and even further downs. At this point, when most of us think “Britney Spears scandal,” we think of one of the events from 2007. However, Britney's 2001 VMA scandal was much more PG, as long as you weren't PETA.

At the 2001 MTV VMAs, Britney performed with a live python and other exotic animals. In a statement, PETA slammed Britney by saying, “We asked her not to do it because the animals - under the bright lights, and with all the noise and just the training that goes into making these cats behave - is stressful for them, but also very cruel, so we asked her to not have the animals onstage.”

In retrospective, Britney is even critical of the performance, saying, “Oh my goodness! It's insane! Why did I do that?”

While there was scandal surrounding this photo, this performance remains one of the most iconic VMA performances to date. It's also a reminder of a simpler time before we saw Bald Britney and the true effects of this level of fame.

4 No Collection Of Britney Photos Would Be Complete With This Denim Disaster

Maybe this photo isn't "scandalous" in the traditional sense, but this list also wouldn't be complete without this photo. Britney Spears and Justin Timberlake, who were America's Sweethearts at the time, showed up to the 2001 American Music Awards like this. And it wasn't even a joke. Like, they genuinely thought they were crushing the fashion game. Though it was 2001 and this may have actually been what crushing the fashion game looked like at the time.

For anyone growing up at this time, Britney and Justin were the ultimate #couplegoals. They met on The Mickey Mouse Club when they were just children, then began dating as the hottest teen pop stars of the time. The pair performed together at the 2001 Super Bowl Halftime Show. Britney even told Oprah, “I would love to be with him forever.”

The couple broke up in 2002, as rumors circulated that Britney cheated on Justin with one of her backup dancers. This rumored infidelity was pretty much confirmed through Justin's “Cry Me A River” music video, in which he cast a Britney look-alike. Britney followed that up with her apology song “Everytime.”

And so, this photo of these matching denim outfits may not seem all that scandalous in and of itself, but it represents a couple with whom our culture was obsessed.

3 Um, That Time Britney Let It All Out

There are quite a few photos of Britney exposing a body part that society had largely decided should stay tucked away. However, many of these photos are more due to the paparazzi's determination rather than Britney's wardrobe. For example, there are countless photos of Britney Spears getting out of cars, in which you can see what color underwear she's wearing or that she's, um, not wearing underwear at all. It's a bit unfair to judge Britney so harshly for such photos. I mean, shouldn't we all be entitled to get in and out of cars?

On top of that, Britney has faced several wardrobe malfunctions on stage. Recently, Britney's breast came out of her costume during a show at her Las Vegas residency. Again, who can shame Britney for this? I mean, you've seen the kind of things Britney performs in and the kind of moves she does. Britney Spears will do a damn backflip on stage if she so pleases, and if her nipple pops out so be it.

However, this nip slip picture kind of feels like Britney's fault, right? I mean, what's in that cup, Britney?

2 Obviously, There's The Time Britney Shaved Her Own Head

In 2007, Britney Spears didn't just shave her beautiful head. She shaved her beautiful head as paparazzi captured every moment of the public spectacle. And so, there will forever be this totally insane looking photo, which cemented Bald Britney into pop culture history for all time. The iconic story is that Britney walked into a hair salon in Tarzana, California and asked the stylist to shave her head. When the stylist refused, Britney grabbed the electric razor and did it herself.

At the time of Bald Britney, many believed she had shaved her head because she feared being drug tested via hair sample. However, it's now more widely believed that this dramatic move was simply a red flag for Britney's mental health, the mental health we all ignored as we devoured tabloid stories about Britney's meltdown. Britney shaving her own head was a cry for help that we either couldn't hear or didn't want to hear.

1 The Time Britney Attacked Paparazzi With An Umbrella

These photos of Britney attacking paparazzi with an umbrella are, again, some of the most iconic and famous photos of Britney's meltdown to date. Of course, these photos helped the press paint Britney as unstable and violent. Though, there is much more to the story than just Bald Britney grabbing an umbrella and threatening members of the paparazzi.

Instead, it's important to remember that Britney was going through an intense and publicized custody battle for her sons with Kevin Federline. On top of that, paparazzi reportedly followed Britney around everywhere she went. This was a woman who was essentially being harassed and stalked by the paparazzi until she finally lashed out. Instead of this story, the media painted Britney as a villain instead of a victim.

By the way, on 2017's 10 year anniversary of the umbrella incident, the paparazzi who hung onto Britney's umbrella auctioned it off for $100,000. I don't know who I'm more interested in - the paparazzi who kept that umbrella for a decade or the fan who paid $100,000 to own an iconic part of Britney's stardom. I honestly want to have lunch with them both.