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Chloe Bailey: Mastering Her Career

In our August 2024 cover story, Chloe Bailey opens up about embracing her confidence, her role in Peacock’s ‘Fight Night’ and her upcoming album Trouble In Paradise.

Source: Dalvin Adams / for HelloBeautiful

The moment Chloe Bailey, 26, appears on screen in Peacock’s Fight Night: The Million Dollar Heist, you instinctively feel there’s a mystery smoldering beneath her character’s surface as the camera lens closes in on her face. Bailey stars as Lena Mosley, a young waitress stifled between weighing who gets to live, and who gets to die. In the upcoming series, these decisions don’t always manifest literally but are threaded throughout each character’s framework. There are hustlers, politicians, entertainers, and everyday working-class people (the character lines overlap and rightfully so) fighting to coexist and define their version of the mythical “American Dream.”

Fight Night, which premieres in September, is based on a true-crime podcast of the same name and details the events leading up to a high-profile armed robbery in Atlanta on the night of Muhammad Ali’s historic fight against Jerry Quarry in 1970. The series is executive produced by Will Packer and Kevin Hart (who also stars in the series) and includes fellow Hollywood heavyweights like Samuel L. Jackson, Terrence Howard, Don Cheadle, and Taraji P. Henson.

Chloe Bailey HelloBeautiful August Cover 2024 - chloe bailey movie and tv shows
Source: Dalvin Adams / for HelloBeautiful

Throughout Fight Night Lena’s character arc reveals a determined woman weighing the role of protector while maintaining her autonomy in a male-dominated atmosphere. It’s art imitating life for Bailey who began her career as a child singing alongside her sister in the Grammy-nominated duo, Chloe x Halle.
Following the release of Chloe x Halle’s 2020 album Ungodly Hour, Bailey launched her solo career in 2023 with her project, In Pieces. She’s gearing up to release her sophomore album, Trouble in Paradise on Friday, August 9.

But unlike most women her age, Bailey wades through the challenges of evolving under an intense spotlight. Finding a way to break through her detractors hasn’t been easy, but Bailey said she’s navigated by trusting herself.

“Sometimes it’s hard because you can’t help but hear the loud background noise. And I admire myself maybe four or five years ago, because people’s opinions didn’t matter that much to me. I was a little more fearless,” she told HelloBeautiful. “But I also think that it’s OK to take constructive criticism, and it’s OK to decide what you want to listen to and what you don’t want to listen to and how you can apply it to yourself,” Bailey said.

Chloe Bailey HelloBeautiful August Cover 2024 - chloe bailey movie and tv shows
Source: Dalvin Adams / for HelloBeautiful

Chloe Bailey Movie And TV Career

Fight Night unfolds slowly, fashioning after a classic whodunit mystery. The characters aren’t easily categorized as “antagonists” or “protagonists,” and their fates weave and collide, building on their weaknesses and strengths.

“A piece of advice that stuck with me during filming, Taraji, she told me … ‘Find your light, pay attention, and find your light’ like where the lighting angles are coming from,” the multi-hyphenate entertainer said.
Bailey, who cut her acting chops in movies like The Fighting Temptations, and her most recent appearance in Donald Glover’s Swarm, admitted she was anxious before filming.

“I was nervous because that’s Taraji and we’ve seen each other in passing and stuff, but we’ve never worked together. So knowing that I got to have that opportunity, I was like, I hope I can step up to the plate and hold my own. And she made me feel comfortable and warm and loved, and I have to truly say the same about Samuel L. Jackson,” she continued.

Chloe Bailey HelloBeautiful August Cover 2024 - chloe bailey movie and tv shows
Source: Dalvin Adams / for HelloBeautiful

Bailey added that Jackson’s compliment during rehearsals “gave me so much confidence that I don’t even think he knew what he gave me to know that, OK, I can do the same with someone as great as him.” An actor’s goal is to be curious about the human condition and ensure the audience gets lost in the characters – suspending their disbelief. Bailey hopes this mentality reverberates during her performance. “As I’m getting older and falling more in love with acting, when people see me on the screen I don’t want them to say, ‘Oh, that’s Chloe Bailey acting.’ I want them to see me as that character, and I want them to see me as Lena when they watch this,” said Bailey. “So I hope I did Lena justice. I hope people watch it and are like, ‘Lena’s a badass, and Lena’s strong. And she knows what she wants, and she doesn’t take shit from anybody.’”

Bailey said she wants to “add some of Lena into my daily life” and drew inspiration from iconic Blaxploitation characters like Pam Grier’s Foxy Brown, and her mentor Beyoncé’s Foxxy Cleopatra. She told HelloBeautiful she’s leaning into her dualities as a confident, eccentric woman who loves “science, technology, and engineering,” and offered pushback to critics who say her sexiness is “contrived.”
“But the fact of the matter is, that women, we are multifaceted. We have so many layers. Yes, I’m so quirky and weird and corny, but then there’s moments where I feel absolutely sexy and confident. Those moments are when I’m on the stage or when I’m with someone that I love. Not everyone’s going to get to see that side of me because that’s for my personal life, but both sides can equally exist,” she said.

Chloe Bailey HelloBeautiful August Cover 2024 - chloe bailey movie and tv shows
Source: Dalvin Adams / for HelloBeautiful

“And what I’m really loving right now, I’m really loving Megan Thee Stallion, how she shares her love for the Japanese culture … and being a sexy black girl who loves anime. I love – with even Doja. She’s sexy with curves and stuff, but she equally rocks her kitten heels … It’s like, yes, we can be sexy on stage, but we also have those cute little quirks that make us who we are. Who says, we just have to be one thing? None of us are just one thing. So when people try to get those viral tweets by saying, ‘Chloe’s sex appeal is contrived because she’s this sweet, nerdy girl,’ why can’t I be both? And it just kind of makes me giggle to myself because I’m like, you have no idea because you don’t know who I am as a person.“

A-Town Down

Kendrick Lamar’s last verse in his colossal hit, Not Like Us, reminded the world, “Atlanta was the mecca, building railroads and trains.” Lamar used his lyrical ability to weave in historical elements about how Black slave labor was used to generate wealth and industrial power, specifically during the 19th century in Atlanta. Fight Night picks up the torch from Lamar’s verse to show the city’s modern trajectory as a mecca of Black entrepreneurs, political power, and entertainment. Hart, who stars in the lead role of Chicken Man, envisions transforming Atlanta into a Black Vegas — and uses street savviness to see it through.

Chloe Bailey HelloBeautiful August Cover 2024
Source: Dalvin Adams / for HelloBeautiful

Bailey, an A-Town native, told HelloBeautiful that she undoubtedly resonated with the city’s placement as a central character in the series. “Being able to go back in time, per se, in my hometown where I was born and raised, and seeing how so much life and culture came from there,” Bailey said. “And because I’m from there, I’ve always known that, but I think people who don’t live in Atlanta or aren’t too familiar, they don’t realize how much of our black culture comes out of there. So it was really cool being able to tell a story that’s based off of something that really happened.”

Bailey recently honored another hometown hero, Usher, at the 2024 BET Awards, where the music icon received the Lifetime Achievement Award, celebrating over three decades in entertainment. The tribute included mostly women (Tinashe, Coco Jones, Marsha Ambrosius, Latto, Teyana Taylor, and Victoria Monét took the stage), and for days following the award show, hot takes circulated on social media critiquing the performances. Society’s venom for Black women and misogynoir became the focal topic of conversation, instead of the night’s honoree.

“I am just incredibly grateful that I got to be a part of honoring a living legend right now and knowing that he’s from Atlanta, my hometown, I just hope that I did it justice during his tribute. And there was so much love and care that went into it, and I’m so proud of everyone who was a part of it because they really gave it their all for him, truly,” Bailey said. “And you can never please everybody. Some people will love it, some people won’t. But knowing that he shared that he loved it, that’s all that matters to me.”

Chloe Bailey Hair Tales

Chloe Bailey HelloBeautiful August Cover 2024
Source: Dalvin Adams / for HelloBeautiful

While the origins of Atlanta’s transformation played a large part in the series, the Fight Night cast also physically transformed to shape their characters. Bailey said she enjoyed going back in time over 50 years to make Lena come to life, adding that her stylist Mona, covered her famous locs with “two to three” wig caps to accommodate her layered wig.

“She would cut the edge of the wig cap sometimes because my head would be getting squeezed too tight, and she just always made sure that it didn’t look like a costume wig,” she said. “And it never distracted you from seeing Lena because sometimes that happens if you don’t have someone who truly cares for how you look on screen in your hair, you could end up looking a mess. But I just loved how much she paid attention and put so much love into my hair, and it really made me feel like Lena, for sure.”

Bailey and her sister Halle are instrumental in shifting visibility around Black women who wear their hair in locs. Throughout their careers, their hair expression became bolder, experimenting with different styles like wigs, extensions, and colors, all while unraveling preconceived notions around the protective style. Hair is a large part of a Black woman’s journey, and there is cause to celebrate the intimateness of expression through hair.

Chloe Bailey HelloBeautiful August Cover 2024
Source: Dalvin Adams / for HelloBeautiful

“I remember there’d be so many women a couple years ago, they’d come up to us like, ‘Oh my gosh, y’all make me want to loc my hair so bad, but I won’t be able to wear wigs or do as many fun hairstyles,” Bailey said. “And it’s like, you can do both. You can do whatever you’d like with your hair. So I’m happy that we’re kind of breaking that mold, and when I go online and I see beautiful women with locs with these wigs or wrapping their hair, it makes me happy to know that sis and I had a part to play in knocking away that misconception.”

Revelations

2024 has been a year of monumental change for Bailey and her family. Late last year, Halle and her partner DGG welcomed the newest member of their tribe, Halo. Bailey said she’s “proud” of how her sister has embraced motherhood and revels in spending auntie time with her nephew, but she also said she’s in no rush to start a family.

“Sometimes we get pressured by society. I just turned 26 and sometimes they’re like, ‘You have to settle down and have kids and do that.’ But I’m like, I can have a little bit more time because I have the best nephew in the world, and it’s like I get best of both worlds,” she said.

Chloe Bailey HelloBeautiful August Cover 2024
Source: Dalvin Adams / for HelloBeautiful

While she hasn’t experienced motherhood, Bailey burst with pride when she talked about the labor she put into her new album, Trouble in Paradise. Bailey said the project was recorded and mastered in St. Lucia and she found solace, acceptance, and creativity in the Eastern Caribbean country.

“I can walk around with no makeup, I can walk around loving my body, I can go to the ocean, truly just pray to God and thank him for the blessings that I have. And it reminds me that life isn’t all about what my career is. It’s not about outer validation, but the inner peace,” she said. “I just really wanted people to feel the peace and the love that this place has brought me, where it was able to open up my creative mind and my creative spirit to literally write my troubles away in paradise. And the album feels like what a summer fling feels like, the back and forth of it, the highs, the lows, the love.”

Bailey, who recently celebrated a birthday, told HelloBeautiful that she wants to continue claiming her totality – basking in the light.

“So this year I want to be more at peace and more disciplined with my emotions,” Bailey said. “That’s my goal for this year, and it’s already been off to a great start where I’m learning so much about myself, where I’m learning the power of not revealing everything all the time, keeping some things to myself. Not everybody deserves access to your thoughts, your dreams, your aspirations, your inner thoughts, or even your emotions.”

Fight Night airs on Peacock September 5, 2024

Editorial Credits

Cover Story: Charise Frazier
SVP of Content: Allison McGevna
VP of Content: Kirsten West Savalli
Editorial Director: Shamika Sanders
Talent: Chloe Bailey
Photographer: Dalvin Adams
Digi Tech: Andrew Ngu
Lighting Director: Byron Nickleberry 
Photo Assistant: Cornell Agee
BTS Video: Brianna Nakatani  Tyler Harp
Wardrobe Stylist: Jason Rembert
Wardrobe Assistant: Wilton White
Makeup: Kenya Alexis
Hair: Fesa Nu
Creative Director: Jordan Benston
Production Company: The Oracle Media
Production: Maisha Peace, Brooke Langley, Camaree Barr
Location: Smashbox Studios

IN THIS ISSUE

Chloe Bailey wore a sexy Tom Ford dress and Tom Ford shoes on the August cover of HelloBeautiful.

Chloe Bailey gets candid about her rich auntie life, folks responsible for her hairstyles, and the lessons she's learned from industry giants.

From Chloe and Halle to Bey and Solange, Black celebrity sisters are a vibe we can't get enough of.

From Beyoncé to the late great Whitney Houston, here are some of our favorite singer-turned-actresses over the years.

Ride or die Chloe Bailey fans know that whether we're talking about hair, beauty, or fashion, switching up is what the entertainer does best.

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