Chloe Bailey: Relationship Red Flags & Redefining Success
with Chloe Bailey
1 Jul 20265 min read1h 15m
TL;DR
Chloe Bailey traces her path from posting YouTube covers at 13 to being signed by Beyoncé after their 'Pretty Hurts' cover hit 23 million views, crediting Beyoncé's advice — 'don't dumb yourselves down for the world, let the world catch up to you' — as the throughline of her career. She opens up about the media's attempts to pit her against sister Halle, the industry pressure to change their natural locs, and how writing 'Have Mercy' was a direct response to being shamed for her body. At 28, she says the key shift is learning to distinguish what matters from what doesn't, doing self-work, and letting go of the hyper-protective role she always played for Halle.
Key Moments
Chloe Bailey
“I wish I had my positivity and confidence that I had when I was younger because it's true. Anything I put on my mood board, any like I would tell because I was like number one beehive. I would tell Hie, I would tell everybody, 'We're going to be the first artist signed to Beyonce.'”
Chloe reflecting on how she manifested being signed to Parkwood Entertainment and how self-doubt erodes that kind of belief as you get older.
“The early advice she gave us, she used to call us her little aliens because we were so like different and like she would say like out of this world and she would always say, you know, the world won't get it yet, but don't dumb yourselves down for the world. Let the world catch up to you.”
Chloe recounting the career advice Beyoncé gave her and Halle during their early days opening for the Formation World Tour.
“With her becoming a mother, I'm not a mom. There's a new level of life she unlocked even before I did. So I have to be like Chloe, you all have different journeys. She is raising her child. This is not she's not your child.”
Chloe discussing the emotional work of letting go of her hyper-protective older sister role now that Halle is a mother.
“It wasn't cool to be young black with short little locks. Like I remember sometimes being in school like it's funny there's this self-portrait of me. I was four and we had to do a self-portrait. And I drew myself like I had like this straight ponytail. And I'm like, Chlo, now I can laugh at it. But it's funny how we see ourselves when we look at our friends and we're like, that's what I'm supposed to look like.”
Chloe opening up about internalizing Eurocentric beauty standards as a child, and the industry pressure to wear wigs over their natural locs for auditions.
“I ended up saying, you know, I'm really upset because people aren't letting me be me in the body that I have. Like, first they tell me, 'Oh, she's amazing. She's being restricted.' Then they tell me, 'Oh, she's showing her body too much.' All of this. And I was like, I really just want to use this song to just get my feelings out and talk my [ __ ]”
Chloe explaining the emotional origin of 'Have Mercy,' written in a session after her Feeling Good performance sparked a massive online backlash.
Chloe Bailey is a singer, songwriter, actress, and one half of the R&B duo Chloe x Halle alongside her sister Halle Bailey. She rose to fame posting YouTube covers as a teenager, which caught Beyoncé's attention and led to them being the first artists signed to Parkwood Entertainment. Chloe has since built a successful solo career and has Grammy nominations to her name. She turned 28 on July 1, 2026, the date this episode was released.
Takeaways
1
Beyoncé told them: let the world catch up Rather than advising Chloe and Halle to adapt their sound to what was popular, Beyoncé explicitly told them not to dumb themselves down. Chloe says this still applies — her music often gets dismissed on release and then called a 'bop' months later. The lesson: being ahead of the market is a feature, not a bug, if you have the patience to wait.
2
Protective roles don't auto-expire — you have to retire them Chloe describes having to consciously rewire her instinct to treat Halle as someone who needs protecting, even now that Halle is a mother. She calls it 'retraining' herself. This is a broadly applicable insight about sibling and close-relationship dynamics: roles assigned in childhood persist long past their usefulness unless actively dismantled.
3
Childhood manifestation beats adult self-doubt Chloe put Grammys, a Beyoncé signing, and a Donald Glover script on her mood board as a teenager — and all three materialized. She argues the reason it worked was pure, unjaded belief, something that erodes with experience. The practical takeaway: re-engage with the specific, vivid goal-setting you did before you knew enough to doubt yourself.
4
Bodily shame, not a wardrobe choice, created 'Have Mercy' The song emerged directly from Chloe being attacked online for a Feeling Good performance that aired on a Juneteenth special — a performance she says she was fully clothed for. She used the writing session to process the double standard of being called both 'too restricted' and 'too sexual.' Creative output as a direct response to public criticism is a repeatable pattern in her career.
5
Industry pressure to 'fix' natural hair starts early Atlanta acting agents told Chloe and Halle as children they'd get more roles with 'regular hair,' leading them to buy lace-front wigs for auditions. Chloe drew herself with a straight ponytail in a self-portrait at age four. The normalization of locs in mainstream media is genuinely recent, and this firsthand account names the specific mechanism — casting agents — by which industry bias gets internalized.
6
The Chloe x Halle hiatus was geography, not conflict Halle's casting as Ariel in The Little Mermaid required her to relocate to London for nearly three years, which naturally forced Chloe to start producing solo. There was no creative falling-out; Chloe spent months in Halle's trailer making beats between rehearsals. Understanding that creative partnerships often pause for logistical rather than interpersonal reasons reframes how we read public 'splits.'