Allow Madison Bailey to Reintroduce Herself

2 weeks ago 7

Introducing In Focus, a monthly feature where we turn the camera on the next-gen talent making waves across entertainment and fashion.

For the last four years, Madison Bailey has cemented her status among young Hollywood elite while playing the loveable, headstrong Kiara "Kie" Carrera, a central member to a scrappy cast of ruffians known as the Pogues in the Netflix megahit Outer Banks. But the 25-year-old knows she can't treasure-hunt on the North Carolina coast forever. With a fifth season hanging in the balance, the actress has her sights on her next act: music.

"I have high hopes this isn't the last for this series," Bailey admits during our interview while promoting Outer Banks' fourth season. She's probably right. The show did amass an impressive 15.5 million views within a few days of part one dropping (part two premieres on November 7), so signs are pointing to more rugged adventures ahead. Compared to the duration of other popular teen dramas—think Gossip Girl, Riverdale, and Vampire Diaries—OBX has only reached its half life at this stage, but as its cast of promising 20-somethings gets older and more eager to grow their careers, the show could be at a crossroad. "I just hope we have the time to know it'll be our last season and really soak in those moments. We all know we're going to be in each other's lives in the long run," Bailey says.

Madison Bailey for Who What Wear's In Focus feature for November 2024.

The cast—which also includes Chase Stokes, Madelyn Cline, Rudy Pankow, J.D., and Carlacia Grant—shares a unique bond. All relative newcomers at the start of the series, they experienced a rapid ascent to stardom. Suddenly, a legion of fans were interested in them. It's a strange experience for anyone, but they had each other. There are group chats, shared TikTok algorithms, and a deep understanding that none of their lives are normal. "There's a lot that runs through your mind, being in the spotlight and being in the industry. When you get with people who are in it, you can have those open conversations, and it's very much needed," Bailey says.

For her next project, Bailey isn't straying far from home, i.e., Netflix. Just in time for Halloween, she is starring in the streamer's time-traveling horror film Time Cut alongside Ginny & Georgia's Antonia Gentry. The movie follows Bailey's Lucy Field as she tracks down her sister's masked killer days before her murder more than 20 years earlier. There are few young women, let alone Black women, who have been welcomed into the open arms of the Netflix cinematic universe like Bailey and Gentry. Their time together on set could be emotionally taxing depending on the day. Bailey jokes, "The only people that truly understand are the people that are going through it."

Between simultaneous press tours for OBX and Time Cut and wrapping a soon-to-be-announced project, Bailey is practically penciling in her life by the minute. To say she's busy is an understatement. During our call, she gives me a peek at her planner to show me her week ahead, and it's enough to give any type B person a heart attack. "Look at how insane this looks," she says, holding the color-coded agenda with scribbled handwriting up to the screen. There's so much to do and such little time, but somehow, she's adding more. At the moment, her focus is on her most personal and grounding project to date—her burgeoning music career.

Bailey has spent time secretly in the recording studio with a group of trusted songwriters and producers honing her sound. Her first single, "The Grey," came out at the end of September, marking an exciting and long-overdue venture for the actress. Over early 2000s–inspired chords, she sings about the empowering feeling that comes with living in two worlds and standing in her power.

For Bailey, much of the appeal of entering this process was that there was no framework. There isn't an expectation for her to quickly release a highly anticipated album for her fans. There are no sale or label pressures (yet!) from her newly signed Roc Nation team. She's releasing music on her terms. "It's so much less scary than I thought it was going to be," she explains. Bailey has been sitting on "The Grey" for a little under a year, waiting for the right time to release it. "It's such a relief that it's out there. … It's such a full-circle moment for me," she adds.

Before acting was even a glimmer in Bailey's eye, she dreamed of being a singer. Music was her first love. Her parents played rock and jazz growing up, paving the way for a nostalgia-inspired, classic musical upbringing. After an overwhelming bout of stage fright in her adolescent years, Bailey quickly pivoted to acting and modeling at the age of 14. Despite the anxiety surrounding live performances, she still sang to herself in her bedroom, tucked away from the prying eyes of nearly everyone she knew. While there are a few grainy videos of Bailey singing covers circulating the internet, she says singing to strangers is the next step in cementing herself as an artist. When I ask if there's a possibility for a show, she's bluntly self-aware: "I do really hope to perform it and share it with people … when there's more than one song to perform," she jokes. "It'll be like 'Annnnddd let's take it from the top!' over and over." For the record, there will be a full setlist in the future. Bailey's still cooking up in the studio and plans to release more singles in due time.

Bailey's decision to make music comes from a deep desire to finally pursue what she's wanted all along, even if no one would have listened in the first place. But listen they did. As of publishing, "The Grey" has over half a million streams."I was just scared of everyone telling me it sucked so bad, which, like, I can take it," she says, laughing. The validation from other people isn't why Bailey is doing it—it's to fill the cup of her younger self. "If other people love it, that's amazing, and if it doesn't mean as much to other people, that's okay," she says.

Bailey is standing in her truth, even if her voice shakes. She's been down the road of public perception with Outer Banks but never with something as sacred to her as her music, and her fans have been nothing but supportive when it comes to "The Grey." While scrolling through the comments on her latest TikTok videos promoting the song, however, I'm struck by something a bit odd: They're all filled with comments about the character, Kiara, and not the person actually doing the craft, Madison. "[OBX] has been the majority of my career. That's what [my fans] know me for. They love the show, and so do I," she says, nodding to the comments. It's hard not to read them when your For You page is filled with Poguelandia from top to bottom. "As I grow as an artist and there's more music out there, people will be able to connect with that, and I can share more of myself as well," she explains.

At times, it's hard to believe that a career-defining character will not outlive and outshine an actor forever—especially when interacting with devoted fans on the internet. (For example, Daniel Radcliffe, a Tony Award–winning singer and actor, is still referred to as Harry Potter by the majority of the public.) How do you step into your future without letting go of your past? It'll take time for people to look past Kiara and see her, Bailey admits, but she's here for the ride. "I'm an actor, and I've always been promoted as an actor. Now, I'm really putting myself out there in a different way," she says. "I'm a singer, and I'm now figuring out the artist of it all."

Talent: Madison Bailey

Photographer: Joelle Grace Taylor

Stylist: Ashley Furnival, Forward Artists

Editorial Director: Lauren Eggertsen

Hairstylist: Miles Jeffries, The Wall Group

Makeup Artist: Kendal Fedail, Forward Artists

Manicurist: Kimmie Kyees, The Wall Group

Director of Video: Samuel Schultz

DP: Kyle Hartman

AC: Nicholas Weaver

Gaffer: Andy Trimbach

Sound: Bobby Vonghom