On Jan. 9, Jamie Lynn Spears remembered a very particular milestone in her life.
It had been exactly 14 years since Zoey 101 premiered on Nickelodeon, earning the network its biggest audience for a series premiere in eight years and becoming an instant hit.
Jamie Lynn was 13, playing a well-heeled kid sent to an ocean-view boarding school at the newly co-ed "Pacific Coast Academy." And with that, there were two Spears sisters lighting up Hollywood—albeit one of them not old enough to drive, let alone accompany her big sis to clubs with the likes of Paris Hilton and Lindsay Lohan.
"I love my little sister and I am overprotective with her, and I don't mind saying that," Britney Spears told Real Access after Jamie Lynn had made her big-screen debut playing a younger version of Britney's character in 2002's Crossroads and became a featured performer on All That.
"My sister is a handful," Britney added. "We are so different. It's so funny—actually, she would be a lot better in this business than I am. Like her personality, she is Miss Diva. She is so full of herself, it's so cute."
A little childhood precocity is, of course, not the same as being difficult or demanding, and Jamie Lynn just so happened to have a firm head on her shoulders at an early age.
"She had to be the center of attention," father Jamie Spears said in the 2016 TLC special Jamie Lynn Spears: When the Lights Go Out. "Britney was like her second mother. She agitated everybody to death...She was bad. But it was because she had a mind of her own!"
Recalling how Jamie Lynn's manager had called her about a small part in a movie, Britney said, "And she was like, 'you know, I don't know if I'm ready for this...I don't know if I'm ready for people always asking me for my autograph—I'm just not ready for all this fame thing.'"
So Jamie Lynn was observant, too, apparently already realizing how fame had affected Britney's life. "She's kinda grown up with it," the pop star acknowledged. "She's surrounded by the whole business since she's been a really young girl. If anything I'm going to be trying to get advice from her," Britney added, laughing.
Indeed, Jamie Lynn was only a baby, literally, when her big sister joined The All New Mickey Mouse Club at the age of 11.
"'Oh, Britney's little sister,'" Jamie Lynn said, referring to how people tended to think of her. "I'm trying to change it to Jamie Lynn Spears, you know. So that's why I try to be taken as a serious actress before I ever move on to doing singing."
And after just a couple of years, she landed her own sitcom.
Zoey 101, shot on location at scenic Pepperdine University in Malibu, was Nickelodeon's most expensive production to date and appeared to be well worth it. It was nominated for an Emmy for Outstanding Children's Program in 2005 and Jamie Lynn won Favorite Television Actress at the 2006 Kids' Choice Awards. The cast won a Young Artist Award two years' running for Best Young Ensemble Performance.
Now everyone wanted to see what Jamie Lynn was wearing, who her friends were and what sort of activities she was into in real life. She was also still technically attending school back home in Kentwood, La., so she had to juggle homework along with learning her lines and making appearances all over the world.
It was in Louisiana that Jamie Lynn started dating Casey Aldridge, the father of her now 10-year-old daughter Maddie Briann Aldridge.
When a fan chimed in about her waiting such a long time to share that detail, marveling "oh wow you didn't quit because you were pregnant," the all-grown-up mother of two replied, "Nope...I went home to finish high school and was going to pursue movies."
As she put it in her TLC special, "I needed to go grow up, outside of the world's view." It also was going to be easier to raise a baby as far away from Hollywood, physically and mentally, as she could get.
With so much Britney-related Spears news already swirling in 2007, it was indeed a major shock when then 16-year-old Jamie Lynn revealed she was pregnant that December.
"I was riding around in my mom's little convertible and I had not been feeling well," she recalled to E! News in a 2013 interview. "I thought it was just stress with work and all kinds of different things. My friend was like, 'Why don't you just take a test?' I was like, 'Okay, I will.' We were filling up with gas, so I went in the gas station and took the test and it was positive.
"So that is the glamorous way that I found out I was going to have my little nugget!"
"It was a shock for both of us, so unexpected," the teen also told OK! in 2007, in her first interview about the surprising turn her life had taken. "I was in complete and total shock and so was he." She said she waited two weeks before she told anybody, except for one person.
"Only one of my friends knew because I needed to work out what I would do for myself before I let anyone's opinion affect my decision," Jamie Lynn said. "Then I told my parents and my friends. I was scared, but I had to do what was right for me."
As far as being pregnant at 16 went, "I definitely don't think it's something you should do; it's better to wait," she added. "But I can't be judgmental because it's a position I put myself in."
Zoey 101's fourth season was already shot and it unfolded starting Jan. 28, with the series finale airing May 2, 2008.
The actress earned her GED in February 2008 (so she actually ended up getting her diploma ahead of schedule) and Maddie was born on June 19, 2008, in McComb, Miss., just like her mom and Auntie Britney.
"That was special, but it was also strange because she's always been the baby, and now the baby was having a baby," Britney, by then under a conservatorship after being hospitalized for psychological evaluations twice in January, told OK! that August. "It was mind-boggling. I was shocked a little bit.
"But it was really cool, and she was happy. When she got to the hospital, we all thought it was going to be an all-day thing, and instead, the baby just sort of popped out. OK, we're happy now!"
If Jamie Lynn was really planning on staying in Louisiana for the foreseeable future to lead a so-called normal life after enjoying the pleasures and weathering the hassles of becoming a star at such a tender age... well, what's "normal," anyway? What she did have was a 24/7 job once her daughter was born, so it was family first before pursuing other career opportunities.
Jamie Lynn noted to Glamour in 2012 that, when Teen Mom first premiered, her first thought was, "Oh my God, I cannot wait to see this show because there's someone else out there. I mean, I feel for those girls. I've been that girl. It does show that motherhood is hard. There were so many times—especially when Maddie would get sick—when I would cry to myself and think, I really don't know what to do. It takes bravery to be a young mom, and it does take bravery to let the world watch."
And like most of the Teen Mom stars, she was no longer in a relationship with her child's father.
"Casey was my first love. Since the day I saw him, I just wanted to marry him and be with him forever and ever," Jamie Lynn also told Glamour in what was her first time speaking in detail about her post-Nickelodeon life since becoming a mom. "I believe in safety and birth control as prevention. But like many young girls...I was really scared to go to the doctor. And I was on a Nickelodeon show, and it [felt] especially embarrassing to ask someone to put me on birth control."
She and Aldridge got engaged but broke up in 2009, after which Jamie Lynn, deciding she was ready to pursue the music career she'd always planned on pursuing one day, temporarily moved to Nashville with Maddie. The young parents reconciled briefly but split up for good in 2010.
"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," Jamie Lynn recalled. "We really wanted to do it right. We loved each other. I will love him as Maddie's father until the day I die."
At the time, in 2012, Jamie Lynn said Aldridge was seeing Maddie one weekend a month. Aldridge is also dad now to a 4-year-old daughter, Skylar, with ex-wife April Watson. He has pictures of both girls from 2017 on his Instagram, but it's unclear what his and Jamie Lynn's arrangement is now. He told Us Weekly, following his Feb. 12 arrest for alleged possession of oxycodone, Xanax, lorazepam and drug paraphernalia, that he was "praying [the arrest] doesn't have an effect" on his custody situation.
"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," Aldridge said. "Whatever I need to do to do that—to not let it happen again."
Back in 2012, Jamie Lynn said that she was dating "here and there, going to dinner or a movie, but nothing further than that. I'm a mother first. I have a little girl, and until I'm serious about someone, he's not going to be around her."
The 21-year-old did hope to be settled down again one day. "I just want to be a soccer mom," she added. "I want to cook dinner every night. I want the kids to come home and be dirty and make the house messy. At the same time, I have to be patient and wait for the right time and the right guy."
In the meantime, her recording career officially got underway with the release of her debut single "How Could I Want More."
"It's seeing it all here and it's real," she told E! News, sharing the excitement about the music she was making. "It's like, 'Oh my goodness, I'm really gonna do this.' It's like my second baby."
She wrote her debut song several years beforehand, she explained to Country Music Is Love. "It was when I was going through this time in my life where my now fiancée, we were kind of in a transition stage. I had just moved to Nashville full-time and I was focusing on being a mom and focusing on my work.
"I was having the struggle of how could I want more? He's a great guy, but I was really was just not in a place to be in that relationship. It's funny, if you fast forward to where I am now and I'm going to marry this man and the song really came full circle. It's an older song, but it still means so much to me. It was written at a very vulnerable time. Every time I sing it, it just brings all that back up."
Mr. Right had come along in the form of business owner James Watson, who proposed in March 2013 after a couple of years together (despite her description of casual dating in 2012, Watson had been in the picture since 2010). He and Jamie Lynn got married in New Orleans on May 14, 2014, two weeks before her first EP, The Journey, dropped.
The bride wore Liancarlo, and Maddie was her flower girl. Britney's sons Sean Preston and Jayden James were the ringbearers.
After the honeymoon, the plan was always to continue to focus on music. Jamie Lynn's song "Sleepover" came out in 2016 and sister Britney and brother Bryan Spears were on hand to introduce her when she performed at the Grand Ole Opry for the first time that March. Also that year, she opened her doors to TLC for Jamie Lynn Spears: When the Lights Go Out, a docu-special chronicling her life from child stardom to teen pregnancy to her big night at the Opry.
"I'm not just a child star, and I'm not just someone's sister," she reflected, "and I'm not just a teen mom."
And then life packed another wallop for the Spears family.
Earlier this year, Jamie Lynn deemed Feb. 5 the "MIRACLE ANNIVERSARY," as it was two years since Maddie was critically injured in an ATV accident. She was operating the off-road vehicle herself, while her grandpa Jamie Spears and stepdad James watched her ride, when she flipped over and landed in a pond after swerving to avoid a drainage ditch. Family members jumped in to get her within seconds but it wasn't until first responders arrived a few moments later that they were able to get her out of her seatbelt.
Two days later, Maddie was awake and talking after a period in which the family wasn't sure what sort of damage had been done. A few weeks later, she was back to her normal routine. So, miracle anniversary, indeed.
A couple months later, Jamie Lynn was back onstage, performing at the Radio Disney Music Awards, where Britney was being honored. That June she basked in the sun—and the applause—at the CMA Music Festival in Nashville.
Then, life literally happened, and daughter Ivey Joan Watson, was born on April 11, 2018.
"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 Lynn told People last May. "It's gonna be a special relationship. Sisters are something special—especially when there's that age gap there."
All the siblings and cousins, including Bryan's daughter Sophia, were together for Maddie's 10th birthday in June.
Nowadays, Jamie Lynn is busy doing extremely normal mom things such as packing school lunches, having taco nights, dressing her kids in matching Christmas pajamas and sharing parenting tales on social media (recently she was asking fellow moms to weigh in on whether sleep regression was a thing and sharing tips on how to keep your kids comfy and cool at the ballpark). She's been working out regularly, keeping it interesting in the gym with different activities such as boxing, jumping rope and rowing. Her sporty family roots for the New Orleans Saints and local LSU teams. Ivey got to witness her first Supercross race in March at AT&T Stadium in Arlington, Texas, and Jamie Lynn takes her along to watch Maddie's softball games.
"Jamie was always a little more rough 'n' tumble," mom Lynne Spears detailed the differences between her two daughters growing up in Jamie Lynn: When the Lights Go Out. "She liked the country music, she liked the fishing, gettin' dirty. She liked playing with the animals. Jamie Lynn was more or less the daddy's girl."
As for her own two girls, Jamie Lynn told The Dopple recently that the age gap has indeed been helpful to her as a mom so far.
"I would think going from one to two children, when they are both under 5 would be a much harder transition," she said. "Maddie is older, so she is able to really be helpful and understanding in some situations that can be tough with a new baby. Don't get me wrong, we have had our tough moments though—just like everyone else!"
Jamie Lynn and Britney try to get their kids together as often as possible, and have been seeing each other more lately while their dad Jamie has been recovering from a colon rupture that required emergency surgery in October, prompting Britney to take an indefinite leave from her new Las Vegas show.
A month ago, a source told E! News that Jamie was "definitely doing better health-wise." He was still recovering in Louisiana and Britney was going back and forth to spend time with him.
Just yesterday, however, amid reports that she had checked into treatment to focus on her mental health, Britney posted on Instagram a note reading, "Fall in love with taking care of yourself. Mind. Body. Spirit." She added the caption, "We all need to take time for a little 'me time.' :)"
"She's balancing her own health as well as dealing with her father's condition," a source shared.
Britney isn't the only one who put work on hold in order to focus on family.
"I'm very fortunate to be able to have all this mama time with my babies lately, but I am missing this.... can't wait to get back...#musicmonday," Jamie Lynn wrote in December along with a throwback video of her at concert rehearsal.
Early last year Jamie Lynn had been teasing a project she'd been working on and it turned out to be a video—but, as she explained to her fans who are wondering when they'll be getting more music from the now 28-year-old singer, who's celebrating her birthday Thursday, life had simply put that project on hold.
"So many of you have been asking when you will get some new music & new content from me, I promise I have been working on it, but life happens & I had take time to be there for my family this year," she shared on social media.
"As you can tell I am pregnant w/ Ivey in this video so this project has been in the works for some time now. It's frustrating that everything has been so delayed but I'm thankful for the support I have been shown while I have been focusing on my family. Can't wait to share."
"I have had new music ready, and a project to go along with it ready since I was pregnant with Ivey," Jamie Lynn told The Dopple, "but a few unexpected family health concerns came up, so I put everything on hold. Family first always, but I am dying to share everything I have been working on."
As far as a potential return to acting to go with the singing, she added, "I'm open to anything that allows me to be creative and connect with my fans, especially the ones who have been with me since the Zoey days."
It's best not to bet against Spears family resilience.