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Jenna Raine: Latest Release "Stupid Cupid," Upcoming EP, & Touring with Joshua Bassett

Interview and Photos by: Orchee Sorker | March 31, 2023 | Nashville, TN

Jenna Raine chats with Hazze Media before her Nashville set which was the first date opening for Joshua Bassett’s Complicated Tour 2023. She shares her story on how she began music, the process behind her latest single “Stupid Cupid," an insight on her upcoming EP “Big Dumb Heart, Chapter One” coming out in May, and her hopes for fans listening to her music.

How would you introduce yourself in one sentence?

I'm Jenna. I'm 19 and I'm a singer songwriter who wants to spread light in a dark world.

How did you get started in music?

I got started in music because I grew up going to church. Worship music was always on in the car, and that's kind of how I fell in love with music. In third grade, the thing that really got me going was I asked my mom and if I could join the talent show. She asked me what my talent was. That's kind of the night of the talent show, when my parents realized that I had potential. I begged for vocal lessons.

Your latest release isStupid Cupid." What was the creative process when writing that song?

I remember I was in the room with Casey Smith and Andrew J. Roberts. We had never written before. Casey was like, "I can tell that you write a lot of music, not from your own perspective and from your own relationships. We should write about you." That was a big change of pace because I never write from my perspective. She was like, "Let's think hypothetically. You and your boyfriend break up because of long distance. How terrible would that be?” Because we've now been dating for three years and I was like, “Okay, this sounds terrible. Sure. Let's do it." So, we wrote a song based off of a hypothetical. I remember we were just kind of trying to brainstorm on how to write the song, and I was looking through my notes and for a really long time I had the title “Stupid Cupid." I wrote it down and didn't say anything. I was very quiet. We had like a shared note, and she was like scrolling through the notes of all the things. She was like, “Where did Stupid Cupid come from?” Then she was like, “Why didn't you say that out loud?” I hadn't really been that used to co-writing. It was one of my first sessions getting back into the groove of it. That was fun.

How does your boyfriend feel about you writing it?

Gosh, we've talked about it briefly. He didn't understand that it was about a hypothetical. I never really told him. That was back when I didn't really know how to have the discussion of what the song's about. I told him a couple months ago. I was like, “Well, it's actually about the pains of distance, and if we weren't standing up together.” He was like, “Oh, I don't like that.” That's not what he had pictured in his head. It's kind of funny.

I saw the video and loved it! So did you kind of have the vision or did you kind of let a director take the lead?

For the video, I worked with the director. For my whole entire solo career, he is one of my favorite people to work with. I had kind of had a direction for a lot of the videos we had worked on thus far. When “Stupid Cupid” was brought up, I didn't think it was going to be the single of the EP that's coming out, so I kind of leaned on his creative direction. He was like, “We've done a lot of plot music videos where there's a storyline. Why don't we just do something that's very creative? It tells a story in just a bunch of different looks and just has fun making videos.” It sounded fun. That's basically what we did. He found a really cool place that had a bunch of different rooms and different vibes. That was more so following his lead, which I wasn't totally used to, which was really cool to have his creative input on the song.

Tell me more about your upcoming “Big Dumb Heart, Chapter One” EP.

This EP is meant to tell the story that I never really got to tell. Back when I was 16/17 in high school, I never really released a big body of work. During that time period, I had a lot of songs that I had written, “Stupid Cupid” was already 1.5 years old. A lot of people wouldn’t know that, but it's kind of a struggle I went through during high school that I’m talking about in the EP. It's really nice to be able to tell that story because I didn't love how all those songs were just sitting there and never gonna be heard. There's a lot of other people going through that specific season where it's gonna help them and gonna really resonate. I might not be able to relate to it right now at this very moment. I was able to a couple years ago, so it's very dear to my heart.

Since it's kind of like a reflection, are you able to see the growth between the years?

Yeah. Chapter one is the first chapter of basically growing into adulthood. I wanted to tell my full story in a really deep way of what I went through and what I don't share even to my family and family cause I'm very quiet about it.

Do you have any focus singles on there?

One of them is “Stupid Cupid” and I have another one coming out before the EP comes out. That's probably the most I can say and keep people guessing what the song is gonna be … but yes there is another focus track.

What is one thing you hope your listeners or fans take away from your music?

Oh, that's such a deep question. There's so much I wanna say, but I hope that they take away a little piece of hope at the end of the tunnel. It's gonna be okay. I hope that through my whole story, chapter one and what other chapters may come along, I hope that it just shows that there is light at the end of the tunnel. You will get hurt and you'll have to heal. Life is just such a beautiful thing. It's amazing that we get to feel these feelings, which is why I want to share every single song because it's so dear to me that everybody really embraces their own feelings. I hope that these songs make people feel less alone in general and just provide a safe space for people.

Last question. How excited are you today and for the future shows you're performing at for Joshua Bassett’s Complicated Tour? How did you kind of get this opportunity?

I am very excited for the show tonight. I haven't performed on a tour in over three years. It's been a really long time. The last time, I actually turned 16 on a tour. That was the last tour I got to perform at. It's just very special to me that Joshua even gave me this opportunity.

I know that we posted jokingly on FaceTime, that's fake … but that's literally how our conversation went down when he asked me to go on tour. We were at a Grammy's event for META. We were talking about God and just random things. Not even talking about music. He randomly said, “Hey, what are you doing March through May?” I was like, “What do you mean? That's a long period of time. I don't know … writing music.” He was like, “Well, I would love it if you'd join me and Lindsey on tour.” We were with all of our teams and everybody's jaws just dropped. It was crazy. It's a really fun story to tell because it was really spontaneous. He told me today, “I just realized like I had never even really seen you perform, but you know, here we are.” That was awesome. It was a really fun way to be asked to go on tour.

That's such a cool story. Thanks for giving me your time to chat with me!

Of course! Thank you! I hope y'all enjoy the show.


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