NYLON Special Report

Reintroducing Jamie Lynn Spears

After a break from the spotlight, the actress-singer (and mom) is ready for her second act.

Jamie Lynn Spears doesn’t have any regrets, but she does have some what-ifs. When she was 16 years old, coming off filming the last season of Zoey 101, the hit Nickelodeon comedy series that made her a household name among the tween set, her managers begged her to go on an audition for what was being heralded as an indie, supernatural romance film. The title? Twilight. “They had to force me. Force me,” she reiterates. “I remember just thinking like, ‘Y’all are insane. I’m not playing a vampire. That is so stupid. Why would I do that?’ But I went and read for that role. I remember sitting in this little room, and I think Lily Collins was there, and I felt so sick. Little did I know, I was pregnant.”

Nearly a decade and a half later, Spears recalls the height of her teenage fame with a bemused laugh. Talking over Zoom from her Louisiana home, wearing a pair of tie-dye sweatpants, she seems to be describing a distant memory from another time, one she has almost forgotten about. Spears is 29 years old now; her daughter Maddie is now 12. “I have a seventh grader,” Spears exclaims, shaking her head in disbelief. “When she goes into ninth grade, someone's going to have to come rescue me, and I'm going to have to have another baby or something.” Mid-conversation, her husband of six years, Jamie Watson, a businessman she met through mutual friends in 2010, sticks his head into the room where Spears has set herself up for the afternoon; somewhere else in the house is their 2-year-old daughter, Ivey.

At this point, Spears simply doesn’t have time to have regrets. On Thursday, she will release a brand-new version of “Follow Me (Zoey 101),” the Zoey 101 theme song she wrote and recorded alongside big sister Britney Spears in 2004. The track follows a recent cast reunion and the announcement of an in-the-works reboot. It’s also the first step of introducing Jamie Lynn Spears 2.0, now a full-blown woman — but one who knows the power of nostalgia. “Maddie [recently] got to meet my cast [for the first time],” Spears says. “It was really strange to see her in that world... It was like living in a dream world.”

Reconstructed Denim jacket courtesy of Miller's Room; Knockers tank top; Maison Miru earring; Lady Grey earring.

“Jamie Lynn’s childhood was like none other,” Lynne Spears, her mother, says now. “She came into this world unexpectedly, yet so adored by all the moment she arrived.” According to Lynne, the youngest Spears child was sweet and smart, and she said “yes” to anything social: basketball, softball, cheerleading, gymnastics. “It was a good thing I had a [Toyota] Sequoia because I carried most of her friends to all of the above.”

Balancing a normal childhood with watching her big sister become the most famous person on the planet, Spears resisted opportunities to try her luck at becoming a giant pop star, another Britney. She was drawn to acting, maybe as a way to differentiate herself. “I'm sure subconsciously, there was maybe some form of that,” she says of her choice to not follow in Britney’s musical footsteps. “But for me, I loved making up characters.” When she got her first acting job at 9, she wasn’t thinking about career trajectory. “I do remember thinking that you can't be a pop star at 9, that it’s not sustainable. I thought, ‘I’ll do that later.’”

But years passed, and she still wasn’t ready. She recalls a meeting she had with a music producer as a young teenager. “There was this time that I went into the studio with a very famous producer-writer who is extremely talented and was phenomenal, and I sang this song where it had the word ‘damn’ in it, and I was like, ‘Oh my gosh. Scandalous. What is everyone going to think about this?’” she says. “This was a very good label and very powerful people that could have had me out there in a second, and I just remember being like, ‘I don't think that I should do music this young because I don't think that I can really be an artist…’”

She was still a kid, busy creating larger-than-life characters — anything for a laugh. “I think I was a little naïve to what I maybe was turning down," she says. "That probably was a good thing.”

Daily Paper jacket and pants; Hanro bra; Clyde belt; Maison Miru earrings; Jimmy Choo shoes.

When it came to acting, Spears was a natural. At 11, she landed a part on All That, Nickelodeon’s long-running sketch comedy show. “The character Thelma Stump that I played on All That is the character I tried out with," she recalls. "I actually invented it on the road with my sister. I combined her bodyguard, Big Rob, and my grandmother, Granny Lexie. I was playing an old lady bodyguard while on tour.” She was the youngest cast member in the show’s history at the time. “Kids are ridiculous all the time, so All That was very nurturing to that,” she says. She was a full-time cast member on the show for two seasons, before moving on to help develop her own starring vehicle at the network, Zoey 101.

She can still vividly recall her first meeting to talk about the show, if only for the setting: Houston’s in Santa Monica, her favorite at the time. “We had dinner, and we talked about what Zoey should be like,” she says. “I just remember it being really important to me that Zoey had a tomboy side to her because that's who I was. I was 11 or 12 years old, so I didn't really have much opinion [on the business side] but I definitely wanted her to be very strong and confident. I do remember that.”

Airing from 2005 until 2008, Zoey 101 followed bubbly Zoey Brooks, played by Spears, and her classmates at the fictional Pacific Coast Academy boarding school, mixing slapstick humor with relatable teen storylines and an aspirational backdrop (the most expensive Nickelodeon show at the time, it was filmed on location at Pepperdine University). The show was an instant hit with critics and viewers; in its first season, it was nominated for an Emmy for Outstanding Children’s Programming, and the Season 3 finale episode was the second most-watched show across all cable channels that week.

To her young co-stars, Spears seemed light-years ahead of them, already a celebrity. “I don’t know what 14-year-old didn’t know who Britney Spears was, and by extension, her little sister, and I also grew up watching All That, so I knew how talented and funny she was. Intimidated might be the right word,” says Sean Flynn, who played Zoey’s best friend, Chase. But Flynn also remembers being struck by how hard she worked. “One of the things that always stood out to me regarding her professionalism was how well she knew her lines. I don’t think she ever messed one up. She always brought her best work to the table.”

Spears remembers being preoccupied with deeply normal teenage stuff. “I was more concerned about going to homecoming," she says. "Sometimes, my favorite part of the day would be when I'd get to go home and eat these Lean Cuisine pasta dishes. Meanwhile, I’m sitting at Pepperdine shooting my own TV show with the beach behind me, like what are you talking about? That's the funny part about all of it is that you're a little kid with this huge thing around you.”

Still, heading up a TV show in the midst of puberty didn’t come without its share of struggles. “Just in the simple things of being in wardrobe every day, and for the first time not feeling great in my outfit or thinking that girl's prettier than me,” she says. “It was all those insecurities that were very much just like every other girl has, but I just happened to be on TV. I got very insecure about a lot of things, especially in young Hollywood, and that was the time where it was very heavy with the paparazzi.”

Remember, this was the mid-aughts. Young stars, some still on the payrolls at Nickelodeon and Disney, were the focus of a new kind of media storm. This was the era of late-night Les Deux ambushes and up-skirt paparazzi shots, with Spears’ sister at the very center of it all. Jamie Lynn herself was never the type to be underage and stumbling out of nightclubs — Google “Jamie Lynn Spears 2005” and you’ll mostly get pictures of her from the Kids' Choice Awards — but still, the pressure and paparazzi witch hunt were very much there.

Looking back on the period, from the life she’s built for herself miles and miles away, gives her an ironic feeling. “I just remember being really, really self-conscious about a lot of things during that time,” she says. “Still, I always say I wish I was as confident as I was at that moment in my life.”

But she’s also come to appreciate the legacy of Zoey. “Now as I've gotten older and I see people who are like, ‘Oh my gosh, I grew up watching this show,’” she says. “Seeing how much the fans really are still so in love with it was really when I understood, right, wow, this is a really big deal.”

In July, the cast of Zoey 101 reunited for a guest appearance on All That (the sketch was filmed before COVID-19 effectively shut down the entertainment industry in March), lighting a fire under a project that had been long-rumored: a proper Zoey 101 reboot. "All That was kind of just to test the waters, and then it was like, 'OK. It has to happen. This just has to happen,'" she says. “That's when the conversations got serious.” COVID-19 has delayed production, but Spears plans to be just as involved as she was when it first began. “Obviously we want to meet her as an adult now, and I do think it should be a show for young adults,” she says. “We want to do it justice for the fans that were 10 and 12 when it first aired, while also bringing in the new generation of fans. Finding that balance will be really important because we want to connect with where people are today. The conversations that we're having right now are creative. ‘What is that story? What is the best way to meet Zoey today?’ We don't want to just do it to do it. We want it to be good.”

The updated theme song is a gift to tide fans over until the reboot, and an opportunity to reminisce about recording the original in 2004 with Britney. “My sister was like, ‘It can't suck,’" says Spears. "She would help me sing exactly how I want to sing because she knew I could sing, but I was so shy about it for some reason. My sister pulled together this song, and then she came in the studio with me and made sure I felt comfortable. But we never actually released a version of it.” The new version is produced by producer/DJ Chantel Jeffries, who worked with Spears to give it a techno edge and update the lyrics for 2020. The 28-year-old is also a former Zoey 101 fan. “I always wished that I could go to PCA. I was like, ‘Mom, please send me to boarding school,’” says Jeffries. “I was so excited to work on something that was so nostalgic and meaningful to me, and so happy to work with Jamie Lynn.”

Spears recorded the song at a studio in Louisiana this spring, after putting in hours of work over Zoom with Jeffries and the rest of her team to make a product that would do the fans right after all these years. “They've been so loyal, and I think in today's world, especially where we're living, I just wanted to put something out there that's happy,” she says. “This is reminiscent of that time, but also the modern Zoey. Who would Zoey be today? What would she sound like? This hits it right on the head, especially for where I'm going with everything. And not just for Zoey, but for me, too.”

Maison Miru earrings.

When Zoey 101 went off the air in 2008, Spears disappeared from the public eye for five years. “That was on purpose,” she asserts. Her pregnancy coincided with the natural ending of the show, leading many fans to blame her personally for the loss of their favorite TV series. “In today's world, immediately I'd have my social media to post something, and it'd be cleared up,” she says. “But even today, people still have their thoughts about it. I didn't become pregnant until probably six months after we wrapped or something like that, but some of the episodes had not aired yet. I think that there was a conversation with Nickelodeon, rightfully so, of, ‘Do we air these episodes?’ But the show had already wrapped and there was never a negotiation to go into any more seasons. We were too old. It was done.”

Spears was already back in Louisiana, trying to reacclimate to normal life while contemplating what might be next for her career, when she realized she was expecting a child with her high school sweetheart Casey Aldridge, with whom she eventually split in 2010. “You have your first love, or what you call love in high school. You think it's forever, and then, oh my gosh, I'm pregnant. I am mortified to have to tell my parents this and my family this. I do not care what TMZ thinks about it,” she says. “That was all I was thinking about: ‘These are the people I love that I have to tell, and also, I'm pregnant. There's a human being growing inside of me, and I'm so young, I'm almost a baby myself.’ I didn't really care about any of that nonsense, but when we did announce that I was pregnant, I did hide away for a little bit during that time and I didn't have a phone. But of course, the paparazzi still found me. It's not like I was in LA walking down the middle of the most popular boulevard; I was in the middle of nowhere Mississippi.” The headlines were even more invasive (“Jamie Lynn Sprouts!”) and judgmental (“Pregnant Jamie Lynn Spears Not Much Of A Role Model”) than what we’d see in today’s media.

“So, I got me a little house. I put a big gate up around it, and I was like, ‘I'm going to stay here, raise my baby, and figure this out because this is real life. I've put myself in this situation, I'm not condoning it or saying it's right, but these are the cards that I have to play,’” she continues. “And I tried to do the best that I could. And yet, sure enough, everywhere I went in Mississippi for that whole nine months, there was always paparazzi on me everywhere I went. But I just knew that if I just stayed away from it long enough that I could give my child some sense of normalcy back in her life.”

Daily Paper jacket and pants; Aliette bodysuit; Hanro bra; Labucq shoes.

According to her mother, Lynne, Spears' ability to focus on what she wants — then, the time and space to adjust to her new reality and prepare for her daughter — is her greatest strength. “She allows few distractions to deter her," says Lynne. "I love her ability to hold her head up through turmoil that would fold most everyone else.” Sure enough, over the next couple of years, headlines about Spears dwindled, and she threw herself into being a mom. “Although her teenage years were few, she grasped motherhood immediately and fully,” adds Lynne. “She focused only on trying to make the best decisions for her baby and herself, and in that order.”

In 2011, Spears and Maddie moved to Nashville, where she quietly began her country music career, writing songs for other artists like Jana Kramer, and working mostly behind the scenes. “It was just me and her there, and my family would come visit, of course, but it was like that important for me to get out of that town, and to establish myself in a different area as a writer, as a singer, and in a world that wasn't so on the front page,” she says. She eventually found her own musical voice, releasing her own EP, The Journey, in 2014, which she dropped just two months after marrying Watson. “During that time, it was like every writing session was a therapy session," Spears says. "I couldn't believe that I had the freedom to say whatever I wanted to say. That was when I realized music as an adult is different than as a kid because it was like I was able to really use it in such a healthy way for myself.”

In the years following, there was plenty of hardship — particularly in a 2017 ATV accident during which Maddie, then 8, almost drowned. But there were good times as well: In April 2018, Spears and Watson welcomed their first child together, Ivey Joan Watson. Now, Spears feels settled, fully at ease in her personal life, even as she navigates the uncertainties of COVID-19 along with the rest of the world. For her, now is the time to focus once again on her career.

Following the re-release of “Follow Me,” Spears is contemplating what’s next for her in the music world, while still working on the Zoey 101 reboot, as well as her role on the soon-to-be-filmed second season of Netflix’s romantic drama series Sweet Magnolias. Six months away from her 30th birthday, she’s come to terms with opening her life back up to the media spotlight. “I was always able to kind of have that bird's eye view of the bigger picture [of fame],” she says. “I was able to see it from a different point of view by watching someone who is obviously now an icon, my sister, go through it. She went from this small town to become this huge megastar that will always be remembered, and seeing the way she handled it so honestly, to me, that was so brave. She was open with me about it. She taught me to protect myself. And I think that I learned how to be strong, but also keep it honest, and it was 100% helpful in every single way.”

“[The media attention is] a whole family thing with us,” she notes later. “But for me, this is what I love to do. This is how I work. I can't not do that. It's not good for me and it's not good for my children to see me deny myself of something I love to do… I don't want to feel like I have to hold myself back in any way because I can be a mother, I can be a wife, I can be a daughter, I can be a sister, and I can be an artist. I put so much into my personal life and really building that to be strong, that now it's time for me. My ultimate thing is just continuing doing stuff that I love and that serves me and my family, and hopefully brings some happiness into the world, and for heaven's sake, gives those Zoey fans what they want. Amen.”

Photographer: Tawni Bannister

Stylist: Kat Typaldos

Art Director: Erin Hover

Hair: Hayley Heckmann

Makeup: Olivia Madorma

Manicure: Mimi Wilson

VP of Fashion: Tiffany Reid

VP Of Creative: Karen Hibbert

Producer: Kiara Brown