Thought Britney was the only famous Spears sister? Think again! There was a time when many thought that Brit’s younger sister, Jamie Lyn, was following in the same footsteps as her older sister. Just like Britney had starred on Disney’s Mickey Mouse Club, Jamie earned a starring role on Zoey 101 at the age of 14. However, it wasn’t long before Jamie’s life took a much different turn.
The celebrity surprised the world in 2007 when she announced her pregnancy with her then-boyfriend Casey Aldridge at the age of 17. She publicized the news in an interview with Ok! Magazine, where she also revealed she’d be taking a hiatus from her work and moving from L.A. to Mississippi to raise her daughter. Shortly after, it was revealed Zoey 101 had been cancelled after only three years on the air.
Although Jamie Lyn received a lot of backlash from stunned fans (and their parents!), the teen handled herself with grace. She gave birth to her daughter Maddie in 2008, and she and Casey were briefly engaged before calling it quits in 2010 for good. Since then, Jamie has returned to the spotlight to pursue a path in country music. She married businessman Jamie Watson in 2013 after two years of dating, and the couple welcomed their daughter, Ivey Joan, in 2018. So much has changed for Jamie in the past decade since welcoming her first child. But take a look at these throwback pictures to see what life was life for the young star before becoming a mom!
20 Smiling Through The Controversy
This photo was taken right around the time Jamie Lynn announced her pregnancy with Maddie. The celebrity looked like she was beaming, but we can only imagine how stressed she must’ve felt dealing with something so personal in the spotlight. Not to mention all the negativity she received from naysayers!
“I think that for me, my biggest concern was, ‘Oh my goodness, I need to tell my mother and my father and my family.’ And that was extremely important to me,” Jamie revealed to People last year about her biggest concern when she discovered she was expecting. We wonder how her parents took it!
19 Her Mom Was On Her Side
In this photo, Jamie Lynn looked different after her surprise pregnancy news hit the stands. And we don’t blame her given the number of photographers she had following her on the daily. Luckily for the teen, her mother was supportive from day one.
Jamie wasn’t the only one who spoke during her OK! Magazine interview. Her mother, Lynne Spears, also gave her perspective. The famous mama said she was going to be there as much as her daughter needed her. Everyone needs a mom like that!
“I want her to ask me to help as much as she wants me to because I will be there for her. I want to be a big part, if she wants me to be,” mama Spears told the publication.
18 She Had To Grow Up Quickly
In this photo, Jamie Lynn was just a newbie to the red carpet. The celebrity looked almost unrecognizable as a young teenager, even though she was only a few years away from welcoming her own baby.
“Overall, I was a very good ... girl who thought she knew everything about love, and clearly, I didn’t,” Jamie Lynn told People about reflecting on her teenage years. “And I think it’s important for young [fans] to know that honesty and that realness that I went through, ’cause it was [frightening]. It wasn’t all rainbows and daisies.”
If one thing is for sure, motherhood made Jamie grow up quickly!
17 Dating The High School Quarterback
Here’s a rare photo of a young Jamie Lynn and her then-boyfriend (and now-baby daddy) Casey Aldridge shortly before the young couple announced her pregnancy. Back in high school, which he attended in Mississippi, Casey sounded like a big shot. So it’s no surprise the young actress was drawn to him.
According to Your Tango, Casey was a talented athlete and played both football and baseball. He was also the leader of the student body during his senior year. “Casey is one of those boys who really has a lot going for him. He’s handsome, smart and very, very charming,” a source told the publication.
16 Facing The Media Head On
Here’s another candid photo the paparazzi were able to catch of Jamie Lynn and her baby bump. The celebrity looked tired and annoyed while doing some errands. And who wouldn’t be if you were heavily pregnant and the paparazzi wouldn’t leave you alone!
“I can’t say it was something I was planning to do right now,” the then-16-year old said in her infamous interview with Ok! Magazine. “But now that it’s in my lap and that it’s something I have to deal with, I’m looking forward to being the best mom I can be.”
And we’d say she’s done a pretty stellar job of being a mom ever since!
15 Partying The Night Away
Before she became a mom, Jamie Lynn was just like any regular teenager (well, a famous teenager, that is). She was often photographed enjoying herself at Hollywood parties and stumbling home late at night, just like in this photo.
“I would say that being a mum is being a mum: It doesn’t matter if you’re in your teens or not, there should be no excuse to not be a great mother,” Jamie has said about being a young mom, Metro reports. “It doesn’t matter what your age is.” She continued, ‘I’m much more sure of myself as a young mother [now]. As a new mother with your first child, you are questioning and guessing everything.”
14 She Considered Britney A "Second Mom"
This photo proves the Spears sisters were always close! Back in the day, the girls would not only make red carpet appearances together but they’d even present awards together. Too bad they’ve never performed together… yet!
When Jamie Lynn announced she was pregnant with a daughter for the second time in 2018, the singer said she hoped her girls would have a bond like she and her sister did. “Me and my sister are 10 years apart, and Maddie and Ivey are 10 years apart, so I’m hoping they have the same kind of relationship where it was like a second mom, almost,” Jamie told People.
She added, “It’s gonna be a special relationship. Sisters are something special — especially when there’s that age gap there.”
13 Kissing Her Co-Stars Goodbye
In this photo, Jamie Lynn posed with her Zoey 101 co-star Creagen Down. Unfortunately, the old castmates have said they don’t keep up with each other much anymore.
We guess becoming a mom made it difficult for the teen to keep up her friendships, especially since she and her baby daddy moved from California to Mississippi shortly after their announcement to get away from the spotlight.
“I was on a Nickelodeon show, so I felt responsible for what these young [viewers] were going to think looking up to me,” she has since shared with People. “And, although Zoey was completely wrapped, they still hadn’t aired the final episodes. So for me, I felt very responsible.”
12 Girls Just Wanna Have Fun
Even though Britney and Jamie Lynn were never really normal teenagers, this photo is proof the sisters still love doing regular girl things! Back in the day, the sisters were spotted renting movies during a casual day out (remember when that was a thing!).
And some things never change. The sisters are still spotted out together regularly, only now they have their kiddos in tow. Last June, for instance, the girls made headlines when their brood got together to celebrate Maddie’s 10th birthday. Jamie posted a photo featuring Britney, Britney’s kid, and their brother and his children, alongside the caption “FAMILY.”
11 An Involved Dad From The Start
The paparazzi couldn’t leave Jamie Lynn nor her baby daddy alone during her teen pregnancy. They often caught candid photos just like this one showing how annoyed the young couple was with the swarm of media attention. Although Jamie and Casey didn’t work out in the end, sources have maintained that he’s always been an involved father.
“When he decides that something is the right thing to do, he is very effective,” a former teacher of Casey’s told Your Tango. “If he decides he’s going to be a great father, he will do whatever it takes to do a good job, whether that means working construction to support the baby, or reading books about how to change diapers.”
10 The Decision Was Easy For Her
Jamie Lynn looked like a total youngster in this photo, especially with the so-mid-2000s pink streak in her hair. However, in just a few short years, the teenager’s life would change forever. Sometimes fans still can’t believe how quickly everything changed.
“I think my whole life I would have to live with knowing what I did or what I didn’t do,” Jamie Lynn told OK! Magazine about her decision to go through with her pregnancy. “I’m the one who has to live with it for the rest of my life,” she continued. “I put myself in this position, an adult position, so I have to act like an adult and take responsibility for what I did.”
9 Not A Girl, But Not Yet A Woman
Jamie Lynn has spoken about how she didn’t feel ready to handle such an adult situation like an unexpected pregnancy, especially in the public eye. The celebrity has since said she knew she had to clean up her act. And we think she did an excellent job handling her new role as a mom!
“I had to make a decision, obviously, that I could go to sleep with every night, but I definitely felt the weight and responsibility of what my actions were,” she told People. “And I had to hold myself accountable, didn’t matter how old I was. I put myself in an adult situation so I needed to handle it like an adult.”
8 And The Custody Battle Begins
Given that her sister Britney was going through a high-profile custody battle when baby Maddie was born, many fans wondered if Jamie Lynn would go through something similar when she and Casey finally broke up.
However, the young parents have stayed relatively quiet about their custody arrangement. Casey has often posted pics of his daughter throughout the years, making it clear he plays a part in his life.
However, Casey did go through a very public custody battle with his now-ex-wife, April Watson, over their daughter Skylar, who was born in 2014. The pair divorced over Casey’s supposed problems. “Casey has a tremendous battle to [tackle],” April later said in defense of her ex, Radar Online reports. “But that does not make him a bad person or a bad dad.”
7 Meet The Spears Sisters
Britney Spears was already an icon when her younger sister began following in her footsteps, first by snagging the lead in Zoey 101 and then dipping her toes in the music industry.
When this photo was taken, no fans could imagine that Jamie Lyn would be the first Spears sister to have children. But then the actress surprised the world a few years later when she announced her baby news.
Nowadays, Britney and Jamie seem closer than ever, often posting photos of them hanging out with their kids. "My sister is in a [great] place right now. I think we need to focus on what an amazing place everyone is in, especially her,” Jamie said in 2016 of her famous sister, Refinery29 reports. “She's kicking [butt] right now!"
6 But It Wasn't Happily Ever After
As we’ve already mentioned, things between Jamie Lynn and Casey didn’t work out in the end. The couple called off their engagement after about a year. But that, unfortunately, wasn’t the end of the drama between the pair.
Casey made headlines again just this past February after he was arrested. The 29-year-old was found passed out in his car while it was still in drive and had a variety of things on him, Us Weekly reported. He was also picked up in 2016 for a similar offense.
“I’m going to do everything in my power to better myself and not have to go through situations like this and make sure it never happens again,” he told the publication shortly after his 2019 arrest. “Whatever I need to do to do that — to not let it happen again.”
5 Pregnant In The Public Eye
Jamie-Lynn officially announced her pregnancy during a 2007 interview with OK! Magazine. As soon as she did, the teenager became a public spectacle and the paparazzi was all over her. The media documented as her bump continued to grow, often shooting candid pictures like this one where the celebrity looked less than pleased to be at the forefront of the news.
"It's about embracing your story. You're not apologizing, or being ashamed of it, because it makes you who you are," Jamie Lynn told Entertainment Tonight in 2016 about her experience being a famous teen mom. "As long as you grow from it, you don't have to apologize."
4 Our Hats Off To Her
While many criticized Jamie Lynn for getting pregnant at a young age, we don’t think she got enough credit for how she handled the situation. From all of the media attention to the dissolution of her relationship, the celebrity handled it extremely well for someone who wasn’t even 20 yet.
For instance, during her interview with OK! Magazine, Jamie Lynn was very adamant that she didn’t want any of her fans following in her footsteps. “I definitely don’t think it’s something you should do; it’s better to wait. But I can’t be judgmental because it’s a position I put myself in,” she told the publication.
3 No More Work Engagements For Her
Jamie Lynn was a pro at giving interviews and reading lines for the camera by the time she announced her baby news. Still, that didn’t stop the teen from taking a step back from the spotlight to focus on her young family. It wasn’t until 2013 that the star announced her comeback as she tried to break into the country music industry.
“I just wanted to get away from it as much as I could, to just go away and be a mom and figure out what I wanted, and to earn a sense of respect back for myself,” Jamie later told Glamour of her need to get away from the public eye. “Move to a town in the middle of nowhere and just raise my child.” She added, “All I could be was a good mother. If anybody had anything to say after that, there was nothing I could do.”
2 The Calm Before The Storm
Jamie looked completely carefree when this photo was taken, not long before the teenager’s world took a 360-degree turn. She says that she had to grow up quickly- and unfortunately, it took its toll on her and Casey’s relationship.
“I was very OCD about Maddie at first. I didn't want anybody to watch her or touch her. I wanted to do it all myself,” Jamie has shared, Refinery29 reports. “I breastfed for almost a year; I couldn't leave her at all. It's sad because my and Casey's love had to turn into an adult relationship so quickly.”
She continued, “There's a slim chance of two young people making it through high school and all that drama, but making it as parents? We tried. We really wanted to do it right. We loved each other. I will love him as Maddie's father until the day I [pass].”
1 Making Waves On TV
Jamie Lynn became a household name overnight when her Nickelodeon show Zoey 101 burst in popularity. The show only ran from 2005 to 2008, but it had a loyal fanbase, which made Jamie’s baby news all the more surprising.
When Jamie first announced her pregnancy, her character Zoey was abruptly put on hiatus from the show and would only make brief appearances from the waist up (incorporating her pregnancy into the show wasn’t an option).
While there was hope Zoey would resume her role after giving birth, the network soon announced the show had been canceled. Many fans believe it was because they were worried about how having a teen mom as the lead actress may affect perceptions.