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Cassadee Pope Returns To Roots Following Hey Monday & ‘The Voice’

Cassadee Pope Session 2023

From her early days as the frontwoman of pop-rock act Hey Monday to winning ‘The Voice’ and exploring the country music scene, Cassadee Pope has propelled her career forward through versatility, resilience, and her personal artistic growth. 

Earlier this year, the acclaimed artist released her latest pop-punk anthem, “People That I Love Leave,” which showcases her return to her roots as well as her mature understanding of how she approaches relationships. Our very own Nick Major had the opportunity to delve into the inspiration behind the song and Pope’s illustrious evolution as an artist. Join us as we uncover the intriguing story behind her musical endeavors and the personal experiences that have shaped her creative path.

You just wrapped up playing your brand new song, “People That I Love Leave,” acoustically for us, which was incredible to hear in that version. I love it because it’s normally pop-punk-ish, but you stripped it down for us. How was that?

It was nice because that’s how the song started, we wrote it on an acoustic guitar. Me, Ali Tamposi, Nick Long, Andrew Luce, and Roman Campolo—that’s a lot of people. [The] five of us just sat at Ali’s studio and we were going through some different ideas. It all started with an acoustic guitar. So I loved that you invited me to play acoustic because that was how it all starts.

It’s always interesting to me because pop punk is so upbeat sounding instrument-wise. And it’s one of those things to where someone just broke down “Dammit” by blink-182 and did it acoustic. And I didn’t even realize how damn depressing “Dammit” is of a song.

Yeah, it’s very sad! 

And hearing the acoustic version that you did today of the new song, it’s one of those moments as well, where you get to hear it a little darker and sadder than the pop-punk version. Talk to me about this song.

I love when songs do that. I love when the very sad, deep lyric is veiled in this fun, uptempo, delicious pop-punk production. And when I was in the session, obviously, we wrote an acoustic, like I said before. So we just went in that direction of the sadder lyric. 

And for me, just personally, I’ve had a lot of disappointments with love, with honestly, men in general in my life, like family, friends. But yeah, I’ve just been let down by life. Some things just have not worked out and it’s been such a bummer. And then you get something awesome, like a good relationship, a good job, whatever it may be. And you just are waiting for the other shoe to drop. Then you end up sabotaging it yourself, because you’re like, “Oh, no, no. This is too good. This isn’t right. Something’s going to happen.” And you end up getting in your own head about it. You push those people away that are actually good for you. That’s what the song’s about—if you think that way, the people you love are always going to leave you because you’re the one that’s like, “This can’t be real. You don’t actually love me like that. I’m sure it’s going to end.” So that’s what we wanted to do, the point I wanted to get across. What we really tried to do in the session was make it a deep lyric that’s actually about mental health, but veil it in this fun production.

It’s a fun new era for you. Obviously, your Hey Monday music, I remember this stuff from back in the day. To watch your journey from ‘The Voice’ was just wild [and] you went on to win it. But that’s where, for about a decade or so, you took the country route. Was that inspired by working on Blake‘s team? Or how did you embark on that side of your music? Because one thing I love about your career is you’ve been able to properly go down different paths and try out different genres.

I mean, I grew up with a lot of country influences and rock influences. I learned to sing on country music, I started taking voice lessons at four years old and I sang Martina McBride songs. It wasn’t like, “Oh, I’ve never done this before.” I went on ‘The Voice’ after having left Hey Monday with a very open mind. I didn’t know what I was going to do. And I was honestly in a bad place. I just was desperate for some opportunity to give me hope again. 

I started doing like Avril Lavigne and Michelle Branch songs on the show. And I felt like I was just getting lost in the mix. So I needed like a really special song that told a story to help me stand out. So I chose “Over You” by Miranda Lambert, which is a song that Blake wrote about his brother who passed. And I just felt like, “OK, this is my moment to tell a story and show that there’s like an artistry there.” Because a lot of people watch those shows and people view it as like, “Oh, they’re doing covers.” But I was like, “This is my chance to turn the song into my own.” And that was the moment that changed everything for me.

​​That was the moment where I was like, “Well, maybe I can do country music and do pop rock also, and make this lane for myself in country music.” And it worked. My first album, I think it went number one on the country Billboard [chart]. It felt like I was living in a dream. I was just like this skunk-haired rock girl. But yeah, it was a very natural progression to go into country music.

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