How SAILORR Forged Her Own Path to Stardom With Her Breakout Hit ‘Pookie’s Requiem’

When Regina George asked Cady Heron if she thought Aaron Samuels’ hair “looks sexy pushed back” in the 2004 teen comedy classic Mean Girls, Lindsay Lohan’s reserved character graphically imagined handling the situation how they would “in the animal world” – by leaping across the cafeteria table and tackling, growling and clawing at Rachel McAdams’ queen bee role. But of course, that didn’t actually happen. “Your hair looks sexy pushed back,” Heron responded defeatedly.

That level of crashing out is what 26-year-old Vietnamese-American singer SAILORR believes “music is for,” she tells Billboard from her producer Adam Krevlin’s Los Angeles crib. As a “retired crash out” herself, SAILORR (real name Kayla Le) has prioritized preserving her peace over staying pressed in real life. But on her 2024 breakout hit and post-breakup anthem, “POOKIE’S REQUIEM,” she rips apart her ex for moving on “to whatever b–ch you got in Bushwick,” while revealing she still feels torn up, even hyperventilating in the outro.

Summer Walker reiterates that while she wishes her ex the best, she knows the worst is yet to come for his new girl on the remix of “POOKIE’S REQUIEM,” which peaked at No. 10 on Hot R&B Songs and No. 8 on Bubbling Under Hot 100, and acted as a lookout while SAILORR trashed her ex’s house in the official music video. “She was like, ‘OK, SAILORR, what do you have me doing?’ And I’m like, ‘Here’s the treatment.’ She was down with all of my shenanigans!” says SAILORR, adding that directing the music video with Walker in it is the biggest “pinch me” moment of her career so far.  

SAILORR’s histrionics are a remnant from her musical theater days, when she dreamed of performing on Broadway while attending an art school in her hometown of Jacksonville, Florida. Prior to graduating high school, she started auditioning for various conservatories around the country, and on her way to a callback at The Theatre School at DePaul University, SAILORR decided acting wasn’t worth getting into debt for – but that music was worth pursuing.

While working a series of odd jobs from florist to lash tech, she released a handful of indie R&B singles and uploaded eclectic DJ mixes to SoundCloud under the alias Sailor Goon, inspired by the Japanese manga series Sailor Moon that she grew up watching. She built her own music community by befriending neighborhood “gear nerds” who taught her how to chop beats, and by virtually connecting with people from SoundCloud, including Adam Kain and AJ Roth of the psychedelic R&B band Cruza, who introduced her to their manager (and now SAILORR’s manager) Zach Migdal. Fast forward a few years later, SAILORR’s new biting, bass-heavy ballad “Cut Up” was SoundCloud’s track of the day last week.

Billboard spoke with February’s R&B Rookie of the Month about paying homage to her Vietnamese heritage with her moniker and blackened grillz, being a “retired crash out,” her ex’s response to “POOKIE’S REQUIEM” and being inspired by Nikki Giovanni on “W1LL U L13?”

What kind of music did you grow up listening to, and how does that influence the music you currently make?

My first introduction to any sort of music was getting my sister’s iPod Nano — I would take that s—t and see what she had downloaded from Limewire. It was mainly ‘90s R&B and hip-hop and 2000s R&B and hip-hop. When I was in middle school, that’s when I decided I wanted to explore music. I was always an avid listener. At that early stage, it was Destiny’s Child and Lauryn Hill, later I discovered Erykah Badu and André 3000. In middle school, I went through a huge alt phase. I was listening to a lot of indie music.

I read that you were a musical theatre kid, and just like me, you’re a child of immigrant parents. How do those aspects of your background affect the storytelling and aesthetics of your music? 

It’s funny ‘cause deep down in my soul, I wanted to be on Broadway. I knew I wanted to be a performer. But of course, my family was like, “So what are you actually gonna do? What’s the vibes?” In general, that area of my life gave me the tools to learn how to survive out in the real world. After I graduated high school, I was like, “What am I gonna do with my life? Am I actually gonna audition for conservatories?” I was like, “No, I’m not going into debt for that. F—k that.” I started making music and hustling that way. In the same way you grow up in a family of immigrants, it teaches you ingenuity and your drive to go further. It motivated me, my parents not really being fully supportive of me doing music. It was just like, “I’m gonna do this s–t forreal and I’mma show you.”

If we’re really being frank, it’s kind of unprecedented. I don’t see anybody else like me making music like me. That territory of truly being myself and being able to present that to people and then have people connect with that, that s—t is still crazy as f—k to me. My life has completely changed because of that one song, and it goes to show that I had it in me. I just had to keep trusting it.

And what kind of music do you listen to now?

Mainly I listen to underground rap. Skaiwater is my s—t. The3 Sacred Souls. SahBabii. Prettifun. TisaKorean. There’s a girl named Nali, she’s hard as f—k.

How did you come up with the name SAILORR?

Growing up watching Sailor Moon — but also my finsta used to be @sailorg00n. I used to go by Sailor Goon when I was releasing music back then and little DJ mixes on SoundCloud. I had to drop it because I was like, “Sailor just rings so well. That’s me.” And to tie it back into my culture and heritage, there was a mass exodus of [Vietnamese] refugees that came [to America] after the war, and they were all sailors essentially. I came from a bunch of fishermen. My grandma, the first thing she did here when she came to America was peel shrimp on a boat.

Where did the inspiration come from to wear blackened grillz?

Way back when, a lot of Southeast Asian women would dye their teeth black using various things, it depends on where you come from. My grandma had black teeth. The very formative years of my life, when my parents were working, I was being watched by my grandma. She was my first look at what femininity is. It was an homage to her, but also, growing up in Florida, everybody has grillz. It’s a perfect intersection of where I come from and then where I come from.

Take me back through the making of “POOKIE’S REQUIEM.” I read you were inspired by the 2000s film Requiem of a Dream.

First of all, it’s a very f—king sad movie. That whole movie represents addiction, I feel like you can tie that into love, relationships. Specifically with that relationship, it was like, “Ah I know this isn’t going anywhere, but we’re here. I’m gonna keep coming back because I love that validation.” During that period of time when I made that song, we had just gone no contact, me and my ex. S—t was weird and off. I really had to take personal inventory and be like, “What is important to me right now?” And during that moment of time, it was me taking back myself. When you’re feeling yourself, you feel like you’re f—king 10 feet tall! A lot of what I said in that song is silly, like, “I’m gonna read you to filth, I’m gonna read her to filth and I’m gonna read me to filth. We’re all going down, b–ch!”

Has your ex reached out to you about the song?

Yeah definitely tried to spin back a couple times. It’s been weird, it’s been awkward. I don’t engage because I have to preserve my energy and my mental health. I can’t do it, it’s too much going on. I hope he’s doing well genuinely, it’s no beef over here. I just use it for source material, but in real life, I’m not a crash out forreal. I used to be, but now I’m just like, “It’s too much at stake here. I can’t f—k my s—t up over anybody.” 

It must be nice to release those emotions through music like, “Let me not crash out in real life, but at least I can crash out through the song. In a different world, this is how I might’ve reacted.”

It’s like Mean Girls whenever they play out the scene and it’s super intrusive but then it doesn’t actually happen. But genuinely, that’s what music is for. I think it is funny that he has heard the song ‘cause know he knows what I know, I peeped game. A lot of the sh— is literal, but it’s also me popping my sh—.

What’s the best way to get through a breakup?

Cry, and then go do s—t that you actually really love to do. During that time, I was keeping myself busy going back and forth to LA from Florida. When I would be at home, I would go to the beach, go to the gym, smoke a blunt with my homegirls. And giving yourself time to really process everything.

Explain the significance behind the fan dance during your From the Block performance last November.

During Lunar Year, there’s a whole ceremony. The lions come out, the fan dancers. A lot of what I do in my music or my performance or my art in general is [a] nod to the things that I grew up with, things that are nostalgic to me. For From the Block, there was a Rush Hour 2 reference.

And what compelled you to hang upside down during your On The Radar performance?! How did you pull that off?

For that concept, I was like, “OK, play on the word ‘sailor.’ I’m going overboard. I’m trying to dock the boat.” It was just funny. I didn’t want to give a regular performance. We want to give it some story, some life. Hanging upside down was the “wow” factor.

That s–t was f—ked up, though. The type of harness you have to get into, all the pressure is in your chest and in your head. I wanted to try doing live vocals, and I probably could have, but because it was the second live performance of “POOKIE’S REQUIEM,” I felt like people were gonna come down on me and be like, “D–n, that’s how she sings?” I’m also upside down, b–ch!

How did you get Summer Walker on the “POOKIE’S REQUIEM” remix?

We met at a studio in LA. She’s so, so sweet. I literally love her music. I used to bump that s—t so, so, so, so heavy, still do. But for any artist to get some sort of props or cosign from my peers – your peers are people that you really, really, really look up to and respect – that s—t was wild.

This song literally opened up connections with people I’ll be able to call as part of my community. The biggest thing about music for me is being able to build with other people, collaborating is my biggest thing. I’m excited that it gets to be with people that I’ve loved and respected for the longest time.

At the end of the remix’s title, you wrote in brackets, “hehe look y’all I made it longer.” Were fans telling you the original song was too short?

Yes, of course. Everybody on TikTok, all the comments were like, “Why the f—k is this s—t only a minute long?” I hear y’all. I do read through them comments now! I hate to admit that…. At the beginning, it was hella hate so I really used to be reading through that shade, trying to restrain myself from responding to everybody. I’m a retired crash out now. [Laughs.] I’m excited to connect with the fans more. I’m so excited to perform live, I’m so excited to start a Discord and actually get to know them.

Do you have a name for your fanbase?

I call them the Fleet, like Sailor’s Fleet!

What did you think of Halle’s cover of “POOKIE’S REQUIEM”?

It was so good, she’s great. I love her.

Who else would you love to collaborate with this year?

I could throw so many people out there. Dream? Doechii, f—king SZA of course. I definitely want to make a song with Skaiwater. Random as f—k, King Krule. The ball could f—king go into any court at this point, who’s trying to work?

The “It’s because I love you/ I’mma get the least of you” lyrics from the bridge of “W1LL U L13?” comes from the televised sit-down conversation between Nikki Giovanni and James Baldwin in 1971. How did you find inspiration from that?

First of all, she’s an amazing person, RIP. I had picked a day to release it, and then she literally passed like two or three days before. I was like, “What the f—k?” In a way, it was a tribute to her because she’s one of the people that really influences me in all of this, as a person outside of the music.

“W1LL U L13?” is about knowing that this person can only give you so much, but you’re still here for it and going through the motions with this person. From that conversation, she was talking about “Why can’t you f—king fake it for me like you fake it with everybody else? Why do I always get the worst parts of you? Aren’t I the one that you love the most?” That whole song is [about how] it’s always often the people that are closest to you that you take for granted.

At the end of last year, you posted two truths and a lie on Instagram. “Before I dropped “POOKIE’S REQUIEM,” I had to get 3 different sets of gold fronts made because I broke 2 of them, and for majority of the videos I’ve been seen in, I wear my Invisalign trays painted black. Before music, I was a bartender, florist, and lash tech and reached out to Chief Keef’s team to be a professional blunt roller (they never got back to me). And I have a forklift certification.” The people still want to know: Which one was the lie? Was it the forklift one?

Yup. [Regarding the first truth], there’s stage makeup by Ben Nye, that’s a makeup brand, that makes tooth paint, and I used to paint [my Invisalign trays] black.

Could you take it off?

Well, I had to change my trays every week anyway, so I was like, “F—k it.” I’m sure I could sit there and scrub it off. I had to literally get three sets of grillz made because I was so irresponsible. The first two months after I dropped “POOKIE’S REQUIEM,” I just kept f—king losing them. I broke them at one point. I was like, “You know what? I’m just gonna paint my Invisalign trays black and go from there.”

So you really did reach out to Chief Keef’s team to be his professional blunt roller?

I did. They never got back to me. 

Why him specifically?

[Sings.] These b–ches love Sosa! The offer is still on the table. I don’t care how busy I am, I’ll come kick it with Chief Keef anytime.

What more can we expect from SAILORR in 2025? Are we getting a debut project?

EP for sure. I’m thinking right now like eight songs — but I don’t know, we’ll see.