Pop singer Britney Spears has become an icon in the music industry, thanks to her hits like “Oops! I Did It Again” and “Toxic.” But aside from her wild success, the star has also become a public figure because of her tumultuous personal life.
Britney was constantly a fixture in the headlines for one thing after another during the mid-2000s. From her quick marriage to Kevin Federline and the birth of their sons to her public breakdown that resulted in big news surrounding a paparazzo’s car, let’s just say there was a lot to report on. If one thing is for sure, Britney has come a long way since those chaotic years, which gives fans just another reason to love her. Nowadays, when she’s not performing in Vegas, she’s focusing on her sons: 13-year-old Sean and 12-year-old Jayden.
What many fans might not remember is that Britney’s younger sister Jamie Lynn Spears had a similarly public spectacle that was blasted in the media in the mid-2000s. In 2007, she announced she was pregnant at the young age of 16 years old, despite being the lead star on Zooey 101. She gave birth to her daughter Maddie the following year, which meant all eyes were on her. Since all of that public drama, Jamie has settled down and welcomed a second daughter, Ivey, in 2018
Both of these sisters have lived through some difficult times while their names were plastered all over the headlines. Check out these 15 times Britney was unexpectedly caught by the paparazzi and 5 times Jamie Lynn was faced with the same thing.
Let's start with the 15 times the paparazzi surprised Britney...
20 Hollywood's Original Trio
Britney Spears, Paris Hilton, and Lindsay Lohan were all at the height of their fame during the mid-2000s. These ‘it’ girls were routinely spotted partying it up in Hollywood together. In this photo, Britney is seen stumbling out of an event with her famous pals looking a bit worse for wear.
Many have speculated that Britney falling in with Paris and Lilo contributed to her downward spiral, which climaxed in 2007 (more on that in a second). Both Paris and Lindsay definitely went through their own rough patches and run-ins with the law, which is possibly why Britney hasn’t associated with these former friends in years.
19 The Day Britney Shaved Her Head
Britney’s bizarre antics eventually climaxed on February 16, 2007, when she infamously shaved her head in front of a swarm of paparazzi. The celeb seemed to be troubled long before the incident and had just completed a stint in a recovery center days before the shaving incident. The stress of her then-ongoing custody battle with her ex-husband Kevin Federline was said to have contributed to her breakdown.
"When she shaved her head, it was quite literally a way for her to try to rid herself of her past," an insider explained to E! News in 2017. "She felt like everything in her life was dictated by someone else. In her mind, people were always trying to tell her what to do, how to act.”
The source continued, “Shaving her hair off was the ultimate rebellion. It was almost a cleansing experience. It was her way of sending a clear message that she was no longer willing to be controlled."
18 Britney Vs. The Paparazzi
Only weeks after her infamous head-shaving incident, Britney made headlines again when she went after a paparazzi car with an umbrella. Seriously.
This photo shows the pop star charging at a paparazzo’s SVU. She had evidently been swarmed by paparazzi while filling her car up at a gas station. Britney’s newly shaven head was on full display as she angrily attacked the vehicle. The following year, Britney was put on two psychiatric holds.
On another note, Daniel Ramos, the owner of the SUV in question, declared that he was selling the umbrella on the 10th anniversary of the incident in 2017, Us Weekly reports. He promised to donate the funds to a charity of Britney’s choice.
17 Can't Stop The Waterworks
Britney was clearly going through an extremely difficult time from roughly 2005-2008, and it certainly didn’t help that it was all being reported on by the media. The celeb couldn’t help but let a few tears show while grabbing a bite to eat with her family.
Paparazzi snapped photos of the singer crying while holding one of her sons in her lap. She made eye contact with the camera and looked absolutely defeated and tired from having the cameras constantly on her. And who can blame her?
"From an early age, I always felt that everyone was testing me,” Britney revealed to Israeli newspaper Yediot Ahronot about what that time in her life was like. “If [something] was not in place, it would have been enough to get me to this point of anxiety. ... a lot of very small, disproportionate things."
16 Not So Great In The Driver's Seat
Another questionable thing Britney made headlines for during her rough years was for not taking proper safety measures while driving with her son. Specifically, fans were outages when photographs were published showing Brit driving with her then-5-month-old son Sean in her lap in 2006.
In response to the incident, the singer insisted she was only doing so to get away from a swarm of paparazzi. "I had a horrifying... encounter with the paparazzi while I was with my baby," Britney said, Daily Mail reports. "I was terrified they would put us in danger. I instinctively took measures to get my baby and me out of harm's way."
But her reasoning did little to reassure upset fans.
15 When It Was K-Fed And Brit Brit
It was an interesting road that led Britney to marry backup dancer Kevin Federline in 2004. Many fans don’t remember that the singer was actually married twice that year. In January, she’d eloped with her childhood friend Jason Alexander while in Las Vegas, though it was annulled less than three days later.
In March of that year, Britney met K-Fed when she embarked on The Onyx Hotel Tour and the two were engaged seconds later in July. At the time, Kevin had just separated from Shar Jackson, who was also pregnant with their second child. Still, the negative backlash didn’t stop Brit and Kevin from getting hitched that fall and getting started on expanding their family.
14 Something Stuck In Your Teeth?
During Britney’s troubled years, there were always paparazzi around every corner waiting to catch her every moment — including embarrassing ones like this where the singer was caught picking at her teeth.
But the point that many failed to see during this time was how all the media attention definitely wasn’t helping Britney get better. Truthfully, it probably just made things worse for her.
"I think I had to give myself more breaks through my [work] and take responsibility for my mental health,” Britney explained to Yediot Ahronotin 2017, explaining how she should’ve taken more time away from the spotlight when she was younger. “There were many decisions that were made for me and that I didn't make myself."
13 Britney Needs To Fire Her Hairstylist ASAP
Not only was Britney making headlines for her bizarre antics during this period in her life, but she was also receiving attention for her unkempt looks. Fans were used to seeing the celeb all dolled up and put-together on the red carpet. But she began to look more and more disheveled in front of the camera.
This photo shows how the singer would often show up to events with her extensions only half finished and her makeup already smudged. Many speculated that Britney was giving her makeup and hairstyling team trouble and refusing to sit down to get fully glam, which only caused her fans to wonder further about what was going on in her personal life.
12 What Co-Parenting Really Looks Like
For a better part of her meltdown, Britney was engaged in a custody battle with her ex Kevin Federline. After the singer’s father took control of her assets, K-Fed was temporarily given custody of their boys while Britney sought help.
Luckily nowadays, it seems like the exes are doing a much better job at co-parenting (they share 50/50 custody, too). This photo shows that Britney and Kevin have no trouble being around each other for the sake of their sons, as they even attend soccer games alongside one another.
"You fall into your routine, and it's really easy now," Kevin told Personal Space in 2017 about co-parenting with his famous ex-wife. "It wasn't always easy, but it's a lot easier now."
11 This Isn't Britney's Usual Ride
It didn’t look like Britney was expecting to have an audience when this photo was snapped. The singer was trying out one of her kids or nieces’ electric cars, which clearly, water bottle in hand. Now that’s a mood. Photos like this prove that Britney still likes to let loose and have fun, just in a different way nowadays.
"Crisis is a strong word. Each and every one of us that starts at a young age need to take into account that you’ve gotta be balanced in order to stay in this industry and to manage your personal life,” the singer told Yediot Ahronotof what getting older has taught her. “Sometimes that’s very challenging. I think I was very different back then, younger, not always knowing what’s good or bad, very instinctive."
10 2007 Was A Bad Year For Britney
Britney looked absolutely miserable when this paparazzi photo was snapped. It was in the prime of 2007 and the singer was trying to escape the swarm of paparazzi following her every move. But her wild antics only made them more obsessed with her.
During her wild years, the singer had several incidents where she was photographed getting in and out of her car wearing no underwear. This only worked to make the paparazzi more enthralled with knowing her every move. At least Brit seemed more distracted by her phone call than with the unwanted attention from all the photographers.
We can’t imagine being photographed literally every time we step in or out of a car, but that was Britney’s reality at this point. On another note- Britney should know better than to be driving while talking on her phone!
9 On The Road To Trouble
Here’s another photo of the infamous ‘Holy Trinity’— that’s literally what the media was calling Britney, Paris, and Lindsay’s friendship in the mid-2000s. All of the girls looked dishevelled leaving an event, showing just how hard Britney used to go back in the day.
Interestingly, Paris has since conveyed that Lindsay simply crashed their evening and she and Brit originally didn’t want her there."[Lohan] totally party-crashed. We were all at the Beverly Hills Hotel at the bungalows during an after-party and then Britney and I wanted to leave to go home. Then [Lindsay] started, like, chasing us and then squeezed in the car,” the socialite said during a radio interview last year, W Magazine reports.
Paris continued, “And it was literally a two-seater SLR — you know, the sports car. She just, like, squeezed in and I didn’t want to [embarrass] her in front of all the paparazzi and be like ‘Get out of my car,’ so I was like, ‘Whatever.’”
8 Not All That, Just A Mess
Yikes! This photo shows exactly how much the stress of Britney’s life in the mid-2000s was taking a toll on her. During a Hollywood event, the starlet showed up with half-finished extensions, an interesting outfit, amateur makeup, and seemingly intoxicated. The evening ended in a series of photos like this one, which shows just how out of character Brit seemed.
Despite her wild years, Britney is said to be more stable than ever. Fans will know the singer has been enjoying a residency in Las Vegas, though it was put on hiatus when it was announced her father was ill. Still, the singer seems to be in a good place when it comes to parenting and performing, which shows just how far she’s come.
7 Britney Gets Her Day In Court
Britney looked distressed in this photo as she pushed past the crowd of paparazzi to get inside an LA courthouse. This was one of many times the singer had to show up to court to battle things out with her ex, Kevin Federline, over custody of their boys.
When their divorce was finalized in July 2007, the couple initially agreed to joint custody of their kids. But a few months later, in October, a court granted sole physical custody to Kevin without publicly disclosing the reason.
The couple got into legal trouble once again in January 2008 when Britney refused to hand over her boys to Kevin’s representatives. The singer was hospitalized as a result and also lost her visitation rights. Kevin was given sole physical and legal custody of the children for the time being.
6 She's Not The Picture Of Safety
Britney became more and more belligerent towards the paparazzi as her struggle continued during the mid-2000s. She was often videotaped telling the photographers off, giving them the finger, or even attempting to film them to show them what it felt like.
In this photo, it seems like the singer was trying to give the media something to look at as she stuck her body out of the sunroof of a moving vehicle. Britney smiled and waved to the cameras, despite this being an obvious safety hazard. Considering the star was also photographed driving with her infant son on her lap at the time, we probably shouldn’t be surprised by this photo.
Luckily Britney has come a long way since 2007!
And here are 5 times when Jamie Lynn wasn't camera ready...
5 When Jamie Lynn Pulled A Britney
To be fair, Jamie Lynn has never made headlines for pulling the same sorts of stunt Britney has. But there have been a few moments the paparazzi have caught her in compromising situations. This photo was taken of the teen after a long night out and she definitely looked a bit worse for wear.
Still, despite how young she had her first child, it would be unrealistic to assume Jamie Lynn never went out in her early 20s. Nevertheless, the celeb maintains that motherhood is and always has been her first priority.
“I put myself in an adult situation, so I needed to handle it like an adult. My age was never an excuse for me — because, you know what, my daughter didn’t ask for that,” Jamie Lynn once told People magazine about being a teen mom.
4 This Sure Isn't Red Carpet Attire
Although Jamie-Lynn is trying to launch a new country music path, the celeb isn’t in the spotlight nearly as much as she used to be.
While she was previously most seen in paparazzi close-ups, now fans get a more regular glimpse of the star through her social media accounts. She often posts cute photos of her and her kids, like this one of her and Maddie in matching onesies.
“I like to say that having my daughter gave me a different kind of voice,” Jamie Lynn told People of how motherhood changed her. “When you have to be strong not only for yourself but for someone else, you grow a whole other layer of skin that you can’t even imagine
3 These Sisters Are All Grown
A decade ago, both Britney and Jamie Lyn were making headlines for seemingly all of the wrong reasons. But nowadays the sisters have an entirely different reputation in the media. When they’re photographed, it’s either at a performance or event for work. Either that or they’re out doing something with their kids, like in this photo where Jamie Lynn went grocery shopping with Brit and her son.
“When my daughter was three months old, I started going to Nashville and writing, and that’s when I really started figuring out who I was and what kind of future I wanted,” Jamie said to People magazine about how she’s changed since having her first child. “And I grew a lot, not only through writing but also through being a bit more private.”
2 The Proof Is In The Pics
While Jamie Lynn Spears never went through as public of a path as her older sister Britney did, she did have her own time in the spotlight. The teen was following in the footsteps of her sister by pursuing singing all while starring on a successful Nickelodeon show, Zooey 101.
But in 2007 her rise came to a halt when rumours began swirling that she was pregnant. The teen eventually announced in an exclusive interview with OK! Magazine that she was, in fact, pregnant with her then-boyfriend, Casey Aldridge. She was 16 at the time, while he was 18.
It was considered quite the news for a young teen actress to be expecting. When she began showing, Zooey 101 writers temporarily wrote her out of the script and continued the season. But Nickelodeon eventually decided to cancel the entire show, and sources say it was because they felt a teen mom wouldn’t look good for the network.
1 Not An Ordinary Relationship
Britney’s sister Jamie Lynn has also had a lot of ups and downs when it comes to her romantic life. Many fans were curious to know who the teen’s baby daddy was when the underage pregnancy rumors began circulating.
In her infamous OK! Magazine interview, Jamie revealed it was her boyfriend Casey Aldridge. After that moment, the paparazzi became obsessed with getting photos of the young couple together, just like this one.
It seems like Jamie Lynn and Casey really tried to make things work for the sake of their daughter Maddie. The actress confirmed their engagement in 2008 and they even bought a house together the same year. However, things got rocky in 2009 when Jamie called off their engagement. She subsequently moved out in 2010. The couple tried to briefly reconcile afterwards but ended things after only a few months in.