How Hailey Knox Pivoted From Viral Acoustic Pop to Experimental R&B: ‘I Don’t Like To Box Myself In’
The For the Best singer is Billboard's R&B/Hip-Hop Rookie of the Month for December.
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Hailey Knox has lived many lives.
There’s the doe-eyed, guitar-toting singer-songwriter who, along with her sister Samantha in their duo The Knox Sisters, performed covers at intimate clubs and coffee shops in her native New York in 2012. There’s the solo act, who drew inspiration from Justin Bieber‘s YouTube take off and Ed Sheeran‘s one-man band performances, as Knox paved her own path with an acoustic guitar, loop pedal and soulful voice that makes up the essential core of her music even to this day.
Then there’s Hailey Knox the teenage internet sensation, who built a massive fanbase on the live-streaming app YouNow, where she performed more covers and original songs from her bedroom, that led to her first record label deal with S-Curve Records in 2015. The following year, she released her debut EP A Little Awkward, a short collection of poignant yet playful adolescent pop songs that felt like they were ripped right out of her diary. She made Awkward with renowned producers Michael Mangini (Joss Stone, David Byrne) and Peter Zizzo (Celine Dion, Jennifer Lopez) – who discovered Knox years ago through her YouTube covers – as well as songwriter Imani Coppola.
Her viral acclaim continued paving the way for her first breakthrough: getting a co-sign from Meghan Trainor, opening for Charlie Puth’s We Don’t Talk Anymore Tour in 2016 and AJR’s What Everyone’s Thinking Tour in 2017, and scoring a nomination in the new social star award category at the 2017 iHeartRadio Music Awards. She kept the momentum going with the release of her 2018 mixtape Hardwired, on which Knox showcased her confessional and cunning lyricism about romantic uncertainty and adjusting to life on the road as well as her boundary-pushing indie-soul sound through fully fleshed out tracks and late-night voice memos.
But Knox truly can’t fit her genre inside any one box. She later dabbled with rap on braggadocious singles like “Butterfly Doors” and “Gucci Prada Balenciaga,” the latter of which interpolates Mike Jones’ 2004 debut single “Still Tippin’,” featuring Paul Wall and Slim Thug. The genre’s self-assured cadence stuck with her most as she continued experimenting with her sound, exploring various musical styles while learning production and new melodic flows through “trial and error,” she tells Billboard over Zoom from her Los Angeles home.
And now, there’s Hailey Knox the multidisciplinary star. SZA sang her praises earlier this year when she teased “Stranger,” a brooding ballad about wasting time with someone you wish you never knew, and “11th Hour,” an intoxicating earworm about a selfish ex wanting to salvage a relationship even though it’s too late. Those singles were eventually included on her 2024 EP For the Best, which she released in July via 10K Projects.
Across its eight tracks, Knox bares all about the intimate lifecycle of her own seven-year relationship through spellbinding vocals that tug at the heartstrings and polished, R&B-leaning production. “We were writing about stuff we go through, which was kind of therapeutic in a weird way,” she says. “Even though we did end up back together through the breaks and everything, I think it was for the best because there’s a lot of love there.” For the Best has garnered 33.5 million official on-demand U.S. song streams through Nov. 21, according to Luminate.
Billboard spoke with December’s R&B/Hip-Hop Rookie of the Month about why producing “opened more doors” for Knox’s genre experimentation, how Russ’ open verse challenge led to her first major collaboration and how she and her boyfriend opened up about their past relationship troubles while co-writing songs on her latest EP For the Best.
When did your fascination with the guitar begin?
My dad taught me [when] I was 7 years old. He would come home and jam, it was definitely a hobby for him. My first song I learned was “Blackbird” by The Beatles, it was very finger style. I grew up in a really musical household. I was in a duo with my sister for a few years. It’s something naturally I’ve always been drawn to.
Which guitar players did you look up to?
I grew up listening to Dave Matthews Band because my dad would listen to him a lot. And Ed Sheeran because he does a lot of percussive guitar stuff that I probably subconsciously picked up on.
When did your interest in making loops begin, and how did you start learning to create them?
The first loop I got was a one track, so I would do a lot of experimenting with that. I was 16 or 17. And the one that I’ve been using in my videos is this handheld Boss RC-500 my mom got me as a gift for Christmas. It sparked this whole different thing because online, people love to see the process and it’s a really good way to get my ideas out without thinking about it.
How often do the loops you create become the groundwork for songs you end up releasing?
It’s 50/50. For the most part, I do it for fun and just jam for hours. And sometimes it’s not even to make a song. But there’s been some instances like “Available For Me” [where] I did the loop not thinking anything of it, posting the video, and people really loved this guitar riff. So I was like, “Man, I gotta make this a song,” because it went crazy viral. It’s an interesting way to see what people resonate with.
When did you start producing?
During COVID, I really dove in. When I worked on my first EP, I had been around producers absorbing as much information as I could.
What kind of music did you grow up listening to, and how has that informed the music that you currently make?
So much different stuff, between what my parents listened to – Stevie Wonder, Dave Matthews Band – but then I also loved Miley Cyrus and Aly and AJ. My first concert was Hilary Duff. I loved those pop girlies and people that really went for it.
And who are you listening to now?
A little jazz, a little Yussef Dayes. Mk.gee. People that are all about the music.
Your music has evolved a lot over the years. A few years ago you were making acoustic ballads and indie pop songs. But now, you’ve dug deeper into R&B. How did you make that sonic transition?
Because I am a music lover, naturally I’m doing a lot of different things and seeing what excites me the most. Nobody has one phase of what they listen to, the same way I make music. I like to explore different pockets. I started out in a singer-songwriter space with guitar. When I started producing is when it opened more doors for me. I produced “Gucci Prada Balenciaga.” I got into a really big rap phase of loving Baby Keem. I love the way hip-hop makes you feel [and] hypes you up. When I produced “Charismatic,” that was a space for me to make a record where I can feel really confident in myself. I have a lot of different sides to me. One day, I feel like the more Hardwired Hailey, but other days, I’m like, “No, I f–k with Doja Cat so much. That could be sick to try something like this.” I don’t like to box myself in.
How did you eventually find your flow?
It was a lot of experimenting with my voice, playing with my tone and seeing what feels the most authentic and natural. I think “Butterfly Doors” hit a little too far one way, and “11th Hours” is where I felt most confident. I was like, “Oh, I like this space right here. It’s a little touch of R&B, but I’m still singing from a place that feels genuine to me.” [Sometimes] the perfectionism kicks in and I’m like, “I don’t want it to feel too perfect.” I want there to be that freeness.
When was the first time you remember going viral?
There were a lot of little moments in my career, but maybe the first was when I collaborated with my friend Juno and we did this video cover of “It’s Strange” [by Louis the Child, featuring K. Flay]. And then the Russ thing was a big moment because I had gone independent from my label. TikTok was hitting at that point, and I was like, “Let me explore this and see what I can do.” Open verses were really big, and I did an open verse to his song [“Remember”] and then he put me on the actual record. To see the power of the internet in that way, I was like, “Wow.” I flew out to his house, and we worked on the song. He was really sweet.
You were an internet sensation on YouNow in 2016. Almost a decade later, you’re experiencing viral success yet again but on TikTok. What are the similarities and differences between your experiences with both platforms, especially as it pertains to promoting and performing your own music?
When I was on YouNow, it was all about livestreaming. There was a bit of collaboration, too, because people go live together, the same way people do now. YouNow is more in real time, telling people, “Hey, I put a song out! Go listen.” Or you’d play the song on live. With TikTok, I’m always trying to find unique ways to promote the song because nowadays, our attention span is zero. [Laughs] I like to lead with the music, regardless of what platform, and show people something I made, whether it’s a breakdown of the beat or something I produced within the record. The passion of what I do comes through.
Last December, you posted a freestyle on Instagram about the “story of my life” that spoke on the challenges of being an artist in today’s music industry, from the faux affectionate moochers to the “algorithm A&Rs.” You sang, “I questioned my career, almost pivoted.” Did you have a Plan B if music didn’t work out?
I do not. Naturally, there’s self-doubt with any artistic thing you do. It’s a full-time job – there’s so much that goes into it day to day, like branding and sessions and being “on” at all times but also finding the vulnerability in opening up and trusting people to collaborate with. I don’t have a Plan B. This is what I’m doing.
The beat for that freestyle was from Drake’s “Stories About My Brother.” Why was that the right choice?
I loved that beat. Conductor [Williams] actually sent me some beats too, I love his stuff. It feels old-school but still modern. He’s really talented.
SZA commented “Ate” underneath the clip, and it’s not the first time she’s publicly supported you and your music. How did you react when you saw her comment, and what does her co-sign mean to you?
It’s kind of wild. I have a hard time really allowing things to sink in like that. I’m like, “SZA? Are you kidding me?” I love her so much.
What was the inspiration behind For the Best?
I was reflecting on my relationship, which I’ve been in for seven years, and I write with my boyfriend a lot. We were writing about stuff we go through, which was kind of therapeutic in a weird way. The majority of the project is [about] relationships and realizing even though we did end up back together through the breaks and everything, I think it was for the best because there’s a lot of love there.
Was it hard to revisit those rough moments with your man?
We’re in a good place, so to revisit these times and relive this stuff that I don’t want to relive, it puts this weird energy in the room like, “Wait, we’re back here?” We’re writing about these emotional times and difficult things we’ve gone through, and still being in a good place, but you’re living in that place, too. That was the hardest part.
[But] we communicate really well, and we find a way to write these unique almost rap bars through melody. We balance each other out in that way, and it’s cool ‘cause we both write and I find ways to put melody to some of his lyrics.
Did it feel cathartic for the both of you?
With “Innocence,” it’s talking a little bit about him being my first love and diving into that hook of “something’s gotta change” and feeling like there’s something that could be better in the relationship, but I don’t know how to let him know that. Those moments of “Do I communicate this, or is it going to ruin our relationship?” So, I guess.
I love the beat breakdown you did for “Don’t Matter” on TikTok. What was the most intricate song to produce on For The Best?
“Don’t Matter” actually was the hardest because it was a whole other song before, like all new verses, it was more guitar-based. And then I ended up reproducing the entire thing last minute because I felt like I’d outgrown this acoustic part of me, not completely, but in that sense of this song. I was like, “I need to reinvent this song somehow because I want to feel excited about it.”
On the contrary, what was the easiest and quickest song to produce?
The reinvention of “Stranger” came kind of quickly. The first record was more in this R&B, slow chill mood. And I was like, “Let me explore because I think it could be nice to bring the tempo up.”
Which song are you most excited to perform?
“11th Hour.” That one’s going to be just a vibe live.
I loved the promo song you made for your tour last month to the beat of 50 Cent’s “Candy Shop.” How did you come up with that idea, from the song itself to the video of you riding around in a blue toy car?
It’s funny, I guess it’s similar to “Candy Shop,” but I literally just made the beat and then people were like, “This sounds like ‘Candy Shop.’” And I was like, “Oh sh–, I guess it kind of does.” I was like, “Let’s find a fun way to promote this tour.” And that was the first thing we thought about. I had that blue car sitting here forever, it was for “Butterfly Doors.” I tried to do a video years ago with it and it was really bad, so we did not put it out. But I used it in the tour video.
What’s been the biggest “pinch me” moment of your career so far?
The moments with SZA and Justin Bieber [following me on Instagram] are really big because they’re people that I admire, and it gives me a little bit of the confidence I need some days where I’m like, “Oh sh–, people f—k with me.”
Manifest your next biggest career accomplishment.
I want to collaborate more with artists next year and put more stuff out without dissecting the sh—out of it [Laughs] and not overthinking my steps all the time. We’re in a world where you’ve got to stay on top of things, but I also don’t want to force anything, so finding that balance for myself.
Are there any artists you’d love to collaborate with in the future?
I love Yussef Dayes, he’s an incredible drummer. SZA, throwing it out there. Justin Bieber.
What’s next for Hailey Knox?
I am planning on releasing some songs top of next year that I’m finishing up now and am really excited about.
