Cassadee Pope admits her career began unconventionally.
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Getting her start as the lead singer of pop-punk band Hey Monday, the Florida native was merely a teenager when they had their big break as an opening act on Fall Out Boy’s 2009 Believers Never Die (Part Deux) Tour, a lineup that included All Time Low, Cobra Starship and Metro Station. Hey Monday’s 2010 EP, Beneath it All, made an impression on the Billboard charts, peaking at No. 25 on the Billboard 200. Over the course of three years, the band scored spots on Warped Tour and opened for the likes of We the Kings, the Academy is…, the Cab and others. Pounding the pavement taught Pope a valuable lesson early on in her career.
“What it taught me that whole time was to make sure that I stop and take in what’s happening around me,” Pope reflects to American Songwriter about Hey Monday’s success. “I get a little sad sometimes thinking about all the things I must have missed being a kid and thinking about the wrong things. That’s the kind of stuff that I learned throughout that experience.”
The singer experienced a massive career shift when she was approached by talent scouts at The Voice to audition for the show. Pope was still in Hey Monday at the time and initially turned down the offer. But when the band went on hiatus in 2011, Pope was living in LA and trying to make it as a solo artist. That’s when she was again approached by the talent scouts and made a life-changing career decision to audition.
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“I’ve always had the punk mentality of those shows being the easy way out,” Pop confesses of her initial resistance. “That was not the case. It was the hardest thing I’ve ever done in my life. When I went on the show, I had no idea where I was going to go musically. I didn’t have any decisions made beforehand. I just said, ‘This is something that I never thought I would do, so I’m just going to go with it and see what happens.’”
Her decision paid off as Pope won the third season of The Voice in 2012. She was the first woman to do so, setting the stage for the next phase of her career. When the show was over, Pope was presented with a crossroads: either go pop or country. Having listened to country music while living in Florida and performing covers of songs she grew up listening to by Martina McBride and Faith Hill on The Voice, the choice was obvious to Pope.
“I didn’t see myself in the genre at all,” Pope remarks of pop music at the time when Kesha was blowing up the charts and “Gangnam Style” by South Koran pop star PSY became a global phenomenon. “I didn’t feel like I fit in.”
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With acts like Florida Georgia Line on the rise and The Band Perry offering hits ranging from the tender ballad “If I Die Young” to the fiery “Better Dig Two” to country radio, Pope felt more at home in the expanding genre of country. “I think I could bring the pop-rock influence that I have into country music, and it would work,” Pope says of her mentality moving to Nashville.
Citing her first year in the city as “amazing,” Pope ended up in the writing room with powerhouse writers like Shane McAnally, Natalie Hemby and Liz Rose. “I really embraced where I came from,” she continues. “It really ended up being so life-giving for me. I felt like I found my voice so easily because people were encouraging and aiding me toward what I already was, which was a country artist with the pop-rock twist.”
Her debut solo country album, Frame by Frame, was released in 2013 and debuted at No. 1 on the Billboard Top Country Albums chart and the Top 10 on the Billboard 200. It featured her breakthrough hit, “Wasting All These Tears,” a Top 10 hit on country radio that won Breakthrough Video of the Year at the 2014 CMT Awards. But as the momentum she had from winning The Voice started to fade, Pope found herself struggling to find her place in the genre and trying to fit the image her label wanted for her, including recording songs she didn’t feel connected to.
“In those tough moments, I learned to listen to my gut because the whole time, it was screaming at me, ‘This is wrong, this is toxic, this isn’t this isn’t you,’” she professes. “I wasn’t at the point in my life where I trusted myself. I do now.”
With a newfound sense of self-trust, Pope is returning to her pop-punk roots with her new single, “People That I Love Leave.” It all started in 2020 when Pope was working on her album, Thrive, which felt “nostalgic” and like she was stepping “outside the boundaries of country music,” she recalls. During a trip to LA to write with her friend Ali Tamposi, who’s behind such hits as “Havana” by Camilla Cabello and Justin Bieber’s “Let Me Love You,” Pope had an epiphany when they wrote a song together that “changed my whole perspective,” Pope describes. “I saw myself in a way that I hadn’t seen myself in so long.”
That song was “People That I Love Leave,” co-written by Pope, Tamposi, Roman Campolo, Nick Long and Andrew Luce. The pop-punk melody and Pope’s fierce vocals don’t take away from the vulnerable lyrics, I don’t wanna say “I love you” / ‘Cause people that I love leave / That’s all that I’ve ever seen / As soon as I hold on / That’s when it all goes wrong / ‘Cause people that I love leave. The lyrics come from an honest place, as it stems from her strained relationship with her dad following her parents’ divorce, past breakups and broken promises in the music industry.
“My goal with this song was to surprise people with its depth,” the singer explains. “Those are some big emotions, talking about the traumas of past failed relationships and being let down by people in your life and how when you find new people who make you feel loved and supported, sometimes you reject that because you’re like, ‘That’s not normal.’ So the self-sabotage that goes into relationships sometimes when you’ve had failed ones in the past is what the song is about.”
Creating from an authentic place, Pope hopes to release an album in 2023 and is working on a collaborative version of “People That I Love Leave.” She also plans to tour and release a series of singles leading up to the album.
“My main focus is making sure that I take listeners through a journey,” she proclaims. “What I want to accomplish with this sound is not lose the songwriting skill that I have crafted over the last 10 years, but bring that in with all of the pop-punk sensibilities. I’m really excited that I’ve found that little niche.”
“Once I let myself do what I love and not think about how it might be perceived or who might not believe it or any of that stuff, that’s when I was really able to write the songs that I wanted to write and think of things that I had a block in my head that I didn’t realize I had,” she concludes. “So it’s been really freeing.”
Photo Credit: Austin McMaines/Courtesy of Big Picture Media
