You might recognize LA singer-songwriter Cailee Rae from her popular Instagram account, where she began posting song covers at age 14 and has since racked up more than 522,000 followers. Just don’t call her a cover artist. Now 18 years old, Rae is putting the focus on her own thoughtfully penned pop songs, like her newest single “Deeper.”
At first listen, the clever song is an electronic-infused bop about craving a meaningful relationship, with sharp lyrics like “I’m tired of lying with liars/ You’re the truth I’m scared to tell.” But it also reveals Rae’s own struggle to find connection as an artist who got her start on social media, an experience she found in some ways transformative for her career but in other ways limiting. “I started to please people more than I was pleasing myself,” Rae says. “[Followers are] just a number. I felt disconnected, and ‘Deeper’ is about that.”
She hopes both meanings will stand out in the single’s stripped-down acoustic music video, premiering here on Billboard.
The track is Rae’s first release in two years: Back in 2016, she dropped her five-track Overthinking EP, including the cathartic independence anthem “Anchor.” Now, she says, “I’m really getting to know fans and share music that’s really me. Before, there was a wall, but now that wall is completely broken.”
Allow Cailee Rae to reintroduce herself with the “Deeper” acoustic video below (and the original here), and scroll on for our conversation about making peace with Instagram, finding self-love and why Rae settled on pink balloons for the bright visual.
What was your childhood like?
I grew up in a little town called Chesterfield [Missouri], which was… interesting. [Laughs] I didn’t quite fit in, but I ended up being OK with it. I have three sisters all three years apart — all older; I was the baby — so each one influenced my music and how I came to liking certain sounds. My oldest sister was listening to, like, Colbie Caillat, and then my young[est] sister was listening to Demi Lovato.
Were you always interested in music as a career?
I always wrote music. That was a passion of mine that everyone thought was going to go away. [Laughs] I slowly got more and more obsessed with it, and then for my birthday one year, my family let me come out [to LA]. I fell in love, and my mom moved out [there] with me when I was 13. I feel like a normal 13-year-old is like, “I don’t want to leave my friends!” But I was like, “I wanna be who I’ve got to be. I have to go.”
Your early single “Anchor” came with a sense of self-love and confidence that’s echoed in “Deeper” as well. Where do you think you got that sense of confidence from?
Writing is my therapy; how I figure things out and navigate life. “Anchor” was [me] trying to tell [myself] that I needed to be able to bring myself up. I realized that every day when I woke up, I was going to be the one who decided how I felt. I don’t think “Deeper” would be a song right now if I hadn’t learned that you have to be your own warrior. Listening to Taylor Swift woke me up to feeling confident in your own skin. She was such a dork, and I was too, so relating to that meant so much to me. I want [fans] to listen to my music and get one step closer to being more confident.
How did you get your start on Instagram?
I started doing covers [on Instagram] when I was 14. Ingrid Michaelson’s “The Way I Am” was the first cover I ever did. I loved the reaction I would get. I did Taylor Swift’s “Blank Space” and just changed one note in it, and people were like, “I can’t not sing it like this now.”
How has your relationship with social media changed since?
I was so much more than just a cover artist, and I felt like that wasn’t seen. The dynamic didn’t necessarily make me happy. It really held me back as an artist. I started to please people more than I was pleasing myself. I would post a cover and someone would get pissed that it wasn’t the one they wanted. It’s interesting to see how people react now, because I’m a completely different artist than I was then. It’s a real connection — I’m really getting to know fans and share music that’s really me. Before, there was a wall, but now that wall is completely broken.
“Deeper” is your first release in two years. What made that particular single feel like the right way to re-enter music?
The second I wrote that song, it felt so authentic. I knew people had to hear it. It really is about connection. Now we have phones, and we talk over [direct messages], and all this stuff, but are we connecting with people? Coming from social media, it was really hard for me. [Followers are] just a number. I would much rather be onstage and see this huge audience. I felt disconnected, and “Deeper” is about that.
What was it like to record the acoustic music video?
I saw this beautiful picture of a pink balloon, and it was imprinted in my brain. I told my manager, “I have a crazy idea, but I think it could look cool.” It took a lot of man-work, but when everyone showed up on set, it just took your breath away. I really wanted the environment to replicate something that’s really beautiful and simple and uplifting. That’s the idea of the song — it uplifts. What I want to do, at the end of the day, is create a little world that people can be a part of.