Cassadee Pope Talks Her Career, “Say It First” & Future Plans

Having first come to considerable attention as the singer of Hey Monday, Cassadee Pope has had quite the career. After winning season 3 of The Voice – and being the first female to do so – her popularity hit incredible new heights and she’s enjoyed success and amassed a huge following on both sides of the Atlantic. She dropped her latest single “Say It First” last month and, with her new album ‘Strive’ out in the Fall, PopWrapped caught up with Cassadee to reflect on her time in the industry, to discover the artists she’s been most influenced and inspired by and to learn what she still hopes and wants to achieve in both her personal and professional life.

I’d like to go right back to the beginning if you don’t mind. When did you first realise you had a talent for singing? Was there a particular moment where music ‘came’ into your life and kick-started your passion for it?

I guess it’s really all because of my sister. She had to stop taking voice lessons when I was four because there was a surgery she had to get to have adenoids removed. And at that time, her voice coach was traveling from Jacksonville, Florida to West Palm Beach, which is a good like five or six hour drive to teach a few students in West Palm. And when my sister kind of had to drop out for a couple of weeks, the voice coach was like: “Does Cassadee wanna try because I’m going to be here anyway?” That’s kind of how it started. I started taking voice lessons with her, when my sister was kind of laid out, and I really had a hard time with it at first, I was really frustrated. I wasn’t getting it. I was really impatient as a kid, if I didn’t get something right away. I still have a tinge of that; I get really frustrated with myself then I want to quit. But thankfully my voice coach at the time was really assertive and like: “No, you can do this. Let’s keep trying” and I threw a few temper tantrums. And eventually, one day we were doing the voice lesson about vibrato and I just started having it all of a sudden and I just started having that kind of wave movement in my voice. I was like; “That felt really good. That’s interesting” and that was kind of the moment where I felt like: “Maybe there’s something to this. Maybe I have something kind of naturally in me that wants to do this and just needed that extra push.” So really since I was like four or maybe five, just deciding this was going to be my, this is my passion – this is what I’m going to focus on.

Were there any particular bands or artists that you grew up listening to that most inspired you in terms of your career path?

So my voice coach actually had me cover a lot of Martina McBride and Faith Hill. I forget who the artist was but I loved singing “Swinging on a Star” – that was my song that I would sing on karaoke and stuff. But yeah, I think, I think it evolved over the years when I was a kid; it was a lot of Martina and Faith, and then eventually it became Kelly Clarkson, Avril Lavigne and Michelle Branch, and it just kept going. And then eventually, I was like, writing my own songs. So, from an early age, it was always a mixture of country and pop.

You first came to people’s attention as the front-woman of the band Hey Monday. What do you remember of that time in your life and career?

I recall – I should recall more, let’s just say that. It was such a blur. Basically what happened was I was playing in bands from, you know, thirteen years old, just around town in West Palm Beach, and the line-ups changed constantly, so you know, I was just always looking for a band. Eventually I found one and my old managers helped me put one together. We ended up getting discovered at a music conference in Atlanta. Then this guy, this A&R from Columbia Records, wanted to sign us but wasn’t sold on the band’s line-up – which made me happy because I wasn’t either. So, I kept my guitar player Mike Genteel, who grew up in the same town as me. The other guys were put together by my old managers and so we just like kicked them out and put together the band of people we love. We were like: “This is the vibe, this is who we are.”

I just remember it being really fast after that, you know, going to New York City, staying there for like three months in Brooklyn and like, taking the subway into New York City to do our record, going on tour like right away. When I was 18 we were doing like our first kind of cross country, like small tour with the The Cab and A Rocket To The Moon. But you know, these Florida kids driving cross-country, it was just a very new thing for us, driving around in a van like lugging a trailer when we were used to just flat when we’re driving over hills in California and Texas and stuff. We jack-knifed quite a few times and got stuck in the snow quite a few times and you know, were giving my mom a heart attack left, right and center.

But I just remember it being just so fun and so, yeah, again fast, you know – the next thing I know we’re on tour with Fall Out Boy and we’re in these amazing countries that I’ve never been to before. We’re doing hours and hours of interviews where there’s like a, you know, like a translator – it was people in Japan knowing our music before we had even been there. It was just crazy. And I just, I think it was – if I had been a little bit older or I had had a little bit more therapy at that point, I probably would have remembered more or just appreciated it more because it sort of happened so fast that it felt like that was the way it was supposed to go.

Now, looking back. I’m just like – we were so lucky to have that trajectory and to have fans that quickly you know, and obviously big bands like Fall Out Boy promoting us along the way helped a lot. So yeah, just looking back, I’m like: “You are a lucky son of a bitch.” I am so proud of everything that I’ve achieved but looking back it was just the opportunities were crazy for such a young up-and-coming band.

How well did that time prepare you for what came next – you appearing on and going on to win Season 3 of The Voice?

That was definitely helpful, having been on stage and on tour a lot. But I will say, I thought it would help me more. I had never experienced anything like that, especially the nerves. I feel really comfortable on stage, I never feel nervous really, even if it’s like a big crowd; I get, I’d get excited. I’m not that nervous, but having cameras and knowing that you’re going to be on national television where millions of people are watching and even internationally people you know, find a way to tune in – that really got to me in terms of nerves – I really, honestly feel it affected my voice. Like, I can’t believe I won. I definitely wasn’t the best singer but I think sharing my story and, you know, just trying to be the most authentic version of myself helped.

But yeah, I think just the endurance you get from being on tour is similar to having endurance when you’re on a show like that, where you’re singing every night and you’re singing every day when the cameras are off, practicing with the band, just rehearsing and stuff. So I think that area helped me and then also the interviews. You know, with that show, half of it is just sitting in a room with the producers talking about yourself and talking about the process and I had done a ton of interviews at that point with Hey Monday, so the media aspect helped a lot too.

A lot of shows such as The Voice, and others, have gotten a lot of criticism from some viewers and music fans over the fact that many of the people who appear on the shows, if they have any semblance of a career at all as a result of appearing on them, tend to fall by the wayside pretty quickly. Do you think said criticism is fair and what advice would you give to anyone considering applying to go on such a show?

With American Idol, no shade, but I think that they create a spectacle of a lot of their artists and I know people show up in tiaras and, you know, like dressing like up like a clown and stuff. So there’s an aspect of like ‘don’t do that if you want to be taken seriously.’ But at the same time, I don’t like, even after somebody does something like that, there’s like this kind of public shaming, public bullying on that show. I think after you get past a certain round, it turns into being about singing and everything but yeah, I don’t really watch it anymore because it makes me really uncomfortable.

But The Voice I feel do a really great job of keeping it about the music. Keeping it about – I mean, obviously, they tell everybody’s story and that’s a thing that I really appreciated. They did a really great job of telling my story and it was very real and authentic. So if anybody was thinking of doing one of those shows, I would first I say do The Voice. Skip all the other ones. Yes, some of them might have a bigger, you know, cash prize and obviously American Idol have a really great record of breaking artists and there’s something to that for sure. But I think you have a better chance of getting your story told authentically and they really look after you; the PA’s on that show, everybody behind the cameras really care and they have counseling readily available and everything.

Another piece of advice would be to just go with your gut because a lot of times those shows and the coaches or the judges on those shows really want you to step outside your comfort zone, and I totally get that approach. But I also think when you’re trying to win a show and you’re really great in your comfort zone, maybe stay there and win and then when you are making your record and stuff and you’re doing demos, that’s when you kind of experiment and have fun and whatever. But I think on a national television platform where you’re trying to win a show, you should just do what you do best and like just get through it.

Over the course of your career you’ve achieved so much from a debut number 1 album, to being Grammy nominated for “Think of You” with Chris Young and being the only country artist to play the 2018 Warped Tour. Could you ever have imagined that you’d achieve so much in such a relatively short space of time?

Okay, well I’m going to be honest – when I was a kid thinking of doing music, I thought I would be like swimming in Grammys by now (laughs) because we just don’t have a concept of how this is going to go or going to work and now that I’m sitting here and I’m 31 and am going to be 32 this month, I am so proud. I’m like, “God, that is a lot.” But looking back when I was a kid, we just think that – we think 18 is like old – we think like 30 is old and we think we’re going to be done and retired by 30. But you know, sitting here now, I’m super proud. It’s like all of these achievements are things that I never; I couldn’t see for myself – like being the first female country artist to play Warped Tour was not a goal or anything in my head that I thought I would work to achieve and I didn’t even know I was working to achieve that, you know? And then the second it happened I was like: “Wow, that is kind of like crazy, historical. That’s nuts.” You know, being the first female winner of The Voice and having a Grammy nomination – all these things I didn’t realise I was working towards, and when I got them, I do appreciate it and I’m super grateful.

You’ve toured with some incredible artists including Maren Morris and Tim McGraw, but if you could share a stage with any other band or artist or perhaps have them open for you, who would you choose and why?

I really like KennyHoopla. He’s a really great punk artist but I think he’s doing it in a very modern, new way that I feel like we are all in this nostalgic phase of just wanting emo back and like wanting to get that feeling back and be a part of that community again, and I think he’s bringing that in a whole new, awesome way. I don’t know if he’d be opening or co-headline at this point; he’d probably headline because he’s just like, blowing up. But my ultimate choice would be to tour with Blink-182. They’ve been my favorite band since I was like, 10 or something, and I just – I’ve always loved their melodic choices. Everything is really catchy but when you really read the lyrics and you go deep into their, into the meaning, they really always make a statement, no matter what it is. Like they’re – everything has always been so honest and so funny – but also there’s like a depth to a lot of their songs that people might not catch because of the catchiness and everything. I just really love them and their live show’s really funny and just epic, so, that would be a dream come true for sure.

The past year or so has been incredibly hard on everyone, but particularly those in the entertainment industry such as yourself due to not being able to tour and work in the manner that you’re so used to. How has the pandemic affected you personally and professionally, especially now that the world is slowly returning to some semblance of normality?

Personally, it was a really reflective time and I realized that I really had some work to do as far as finding my worth in my job because I think, I don’t want to think this way, but I think it could all go away and I – there could be an accident, there could be something where it all – I can’t sing anymore and Covid really made me think about that. Like, I love what I do and I feel happy doing it and it fulfills me so much, but I can’t just face my worth off of my job. And so I really had to think about that and look into that and you know, for like a month, really of not writing or anything, just really dive into that.

I think I made some great headway and really used some tools I’ve accumulated over the last few years of therapy and stuff and just kind of landed in a great place of like: “This is what I do. It’s not who I am.” Once I got to that place, I was ready to start writing and tried the Zoom thing which actually was amazing. Then I wrote an album on Zoom basically last year, and the reason I’m going more the pop-punk country route is because of the pandemic and it is because of the stillness I’ve been able to have to sit and think and reflect about what makes me happy, My boyfriend and I have a house together and through the pandemic just having pop-punk nights where we just like, go back and forth and share our favorite pop, punk bands; that really opened my eyes to like, if that makes me that happy then, I mean I can’t imagine what more you know a more pop punk album for me could make my fans feel, you know, because like over the years they’ve all been wanting Hey Monday to get back together and I’m not 18 anymore, so doing that music now feels weird. But, a newer version of that and a more mature version of that feels really right and so musically, it just really made me land in a place where it feels real for me. I don’t know where it’s going to land, how well it’s going to do, but I’ve never felt so sure of this being the right move. I’m not scared. I’m not thinking about how successful it may or may not be. I’m just doing it because it makes me feel awesome. So yeah, both personally and musically. I think I’ve grown quite a bit over the last year.

You shared your latest track “Say It First” at the end of last month. What made you think it was the right choice for a single release?

I’ve been holding on to that song for a while and thinking about just sort of the laying out of this project before the album. I wanted to really hammer home what this project is going to sound like and I felt like “What The Stars See” was a great kind of introduction to it. It’s pop rock, but it’s very country as well, and I wanted people to feel this like, easy transition and for it to be like a bridge into the new project. And then it was really hard to choose the second single because I was like: “Do I give them like one of the more rocky songs? Do I give them one of the more country songs?” And then I felt like “Say It First” was a great kind of double-down of like, this is the sound – it’s going to be in your face; it’s going to be pop rock with sprinkles of country. I felt like it was like continuing the story and it’s not like in chronological order by any means, but just the whole aspect of being bold in your decisions and saying it first, whether it’s breaking up with somebody or saying I love you first, whatever it is – saying anything first takes a lot of courage. “What The Stars See” you know, I felt like it took courage to say “I wish I could see what you’re doing right now.” It’s not something that you want to admit, but that’s what this album is going to be. It’s all about just saying the things that are hard, that are revealing, that are, you know – it’s a storytelling album. So, I wanted to continue that story with “Say It First.”

Your new album ‘Strive’ is out in the autumn. Without giving too much away, what can you say about it? Do you perhaps have a favorite track or does that change every time you want me to come back to it as you get closer to its release?

I think my favorite track is probably a song called “Tomorrow Night.” I keep going back to that one. It’s just one that makes me feel really happy and I love a breakup song. I love a heartbreak song; I love writing them. But really when I write a love song that I am excited about, that’s when I know “Oooh, okay, I’ve really got something here”, because it’s hard for me to not hear a love song I’ve written and think “That’s so cheesy.” So I was really proud of that one and you can sing along to it. It makes me want to like get on stage ASAP because it’s just that kind of song. I leaned more into my Weezer influence; their ‘Blue’ album was really important to me and my influence as an artist. So I really leaned into that and I love the production on it. It’s – we didn’t quantize anything and we didn’t make anything super squeaky clean – we kept everybody very loosey-goosey in the band when we were tracking and we just left that spirit in there; we didn’t try and cut and paste or anything like that, so it’s probably one of the most organic songs on the record as well.

With the world starting to open up again and many artists including Billie Eilish announcing new tours, are there plans in the works for you to tour in support of the new album?

Yeah. I have some shows this month; a festival here, a fair there. In the Fall, I’ll probably be sprinkling in some more shows, but there will definitely be a tour in the winter/spring of next year – of January I’m saying. I’m really excited. There’s some really great team changes happening in the booking side of things, so there’s some new blood that are really excited for the project and we haven’t really announced that change yet but just, you know, to give you an idea. It’s definitely leaning more towards the pop-rock side and just expanding beyond the country festivals and the country tours because that’s, that’s my goal – I want to play all of them and I shouldn’t be restricted to any one. I’m going to be bopping around a lot next year; it’s going to be awesome.

So aside from the album release, are there any more plans or projects in the pipeline you can tease? Have you perhaps chosen what your next single is going to be?

I do actually. I have a really great team who are constantly pushing me to look ahead, and I am very much like: “Okay, we just did this thing, let’s sit in and let’s enjoy it. Let’s see how it does”, whereas like my team are like: “Okay, yes, definitely celebrate the wins, but we do need to think about the next thing so that we can get it on the docket.” So the next single is definitely chosen and I have a whole video in mind for it that I’m going to co-direct – my first time directing a music video – so yeah, it’s all going to be really cool and it’s going to keep coming out, like there’s nothing stagnant happening through the rest of the year for sure.

Finally then, you’ve been a staple of the music industry now for many years, since the age of about 18 and you’ve achieved so much. With that in mind, what’s left for you to tick off your personal and professional bucket lists and at what point will you be able to look yourself in the mirror and say: “I’ve achieved everything I wanted to and more” and look back on a happy, fulfilled life and career?

I think like, per my conversation earlier about you know self-worth and my music or in myself, I think as long as I’m in a happy relationship whether that’s being in, you know, a domestic partnership, or married – whatever it is – just being happy and that communication always being open and honest. I’d love to have a family someday and you know, teach my kids how to leave this world better than we found it. That to me is like success, and then if I could host and be the musical guest of SNL that would be – then that’s really when I can like, die happy (laughs).

Check out the video for “Say It First” below and for more information on Cassadee Pope, visit her website, give her page a like on Facebook or follow her on Twitter and Instagram.