Cool People Know: Jessa (Q & A)
BRONX-BRED + BROOKLYN-BASED ARTIST JESSA IS CONFRONTING THE REAL LIFE STRUGGLES OF THE HEALING PROCESS — with her latest release, “Astrology Online”. This track combines some of the artist’s favorite genres like alternative pop, contemporary R&B, and 80s rock to form her own unique sonic expression. It’s a track about wanting to push forward in healing but being restricted by the anxieties of your past — all while relatably supplementing therapy sessions with social media astrologists when real life gets too overwhelming.
jessa has been passionate about performing since she was a kid and has been releasing music since 2016. Throughout her journey as an artist, she continues to explore her eclectic sound, pull inspiration from the community around her, and create songs that feel most authentic to herself. Read below to dive into the recent release, her artistic growth, Geminis, and more.
SIICK: How’s your relationship with New York?
JESSA: Toxic (laughs). I love New York. I find myself amongst a lot of creatives who inspire me more than just the energy of the city itself. A lot is going on and the energy shifts a lot so my emotions towards this place range a lot. Any day I can hate everyone on the street then an hour later I'm like “everyone is so nice”. But I do feel very tied to the city and I'm sure it inspires me in many ways I can’t articulate.
SIICK: What does your recent release “Astrology Online” mean to you?
JESSA: The song is about not being ready to take the next steps in growing/healing so you find comfort online. I’m so happy it’s out. It’s nice to reflect on where I was in that moment. I go in and out of talk therapy but sometimes, when therapy feels too much, I’ll supplement with the TikTok ladies telling me what’s going on with my life. It’s all in jest — I’m not even that familiar with astrology — but there’s something validating about it. Sonically, I love it. I was listening to a lot of Mk.gee when we made it so that definitely inspired us.
SIICK: I have to ask: what’s your sign? How do you think it applies to you as a songwriter?
JESSA: Gemini. I don’t know much but I’ve heard that that sign is kind of controversial. I think people can see Gemini’s as “two-faced” but for me, I don’t think it’s that. It’s duality. My music is so heavily based on my raw emotions. I’m highly sensitive but I can also have a really sharp tongue. That all goes into my songwriting.
SIICK: How did you go about filming the music video for this?
JESSA: I filmed it with my friend Danica Robinson. The goal was to speak to the joke of it all — finding validation in things that pop up on my phone saying “he’s thinking of you” or “you’re going to make a lot of money this month.” So we went with the concept of a free astrology stand. Sonically and lyrically, it’s not super light, so It was fun to play into the more fun parts of the song and not the deeper, emotional aspect. Like, “yes, these are my real emotions but it’s not that deep. TikTok is here for me” (laughs).
SIICK: How do you think your artistry has changed in the last year or two?
JESSA: I’m constantly finding my sound more and more. Right now, I’m sitting on a lot of demos that are more and more cohesive. In the past, I was taking on too many sub-genres and things weren’t sounding like there was a strong enough thread between them. It’s something I’ve struggled with since I pull inspiration from so many places and I listen to so many different types of music as we all do. Recently, I’ve been weeding through the questions of “what do I love to listen to?” and “what’s me?”. That’s been my biggest cognitive effort. My producer good.will and I just work really well together. We have the same taste and he’s been really instrumental in helping me find that sonic thread.
SIICK: What goals or aspirations are you looking forward to reaching for the next few months?
JESSA: I want to perform more. I hadn’t sought out any opportunities last year because of my health issues — it just hasn’t been a priority. Incrementally, I’m starting to feel better so I feel ready both mentally and physically to get back on stage again. I’d love to open for artists who really inspire me. I also want to release more frequently this year.
SIICK: Who’s an underrated artist we should all be listening to?
JESSA: Can I give you two? sectiontoo is great. He’s here in New York and is childhood friends with my producer so I’ve been listening to him a lot. And also BANKS. I’m obsessed with the song “Deadend”. It’s so good, you must listen.
SIICK: What was your favorite album of 2024?
JESSA: This is not going to make me sound cool but the Wicked soundtrack. But also Forever by Charly Bliss. My friend opened for them so I got to see them live a few times and they’re so good on stage.
