Sam DeRosa’s success story is a perfect example of why you should never give up on your dreams.

The singer/songwriter spent years playing tiny gigs in her quiet Upstate New York hometown before moving to Los Angeles in 2017 to forge a songwriting career, quickly penning a surprise record-breaking hit with Lovelytheband’s “Broken.” Two years later she went on NBC’s Songland with the intention of giving away her track “Pill for This” to guest judge Charlie Puth, whom she’d once tutored in English as a student at Berklee College of Music. Following a performance of “Pill for This” and a subsequent standing ovation from Puth and hit-maker judges Ester Dean, Shane McAnally and Ryan Tedder, in an unprecedented move for the television show DeRosa was told that she should keep the song for herself.

Her Songland appearance led to a contract with Sony’s Monument Records, and “Pill for This” ended up becoming the lead single from her debut EP The Medicine, which released November 13.

Sam DeRosa recently hopped on a Zoom call with PopCrush to discuss Songland, The Medicine and her latest co-writing credit on Dixie D’Amelio’s debut single “Be Happy.”

Your appearance on Songland might lead a lot of people to think that your success came overnight, but you've been working at it since you were quite young. Can you share a little bit about that journey?

I feel like every overnight success story is actually years of work for a moment that seems like it happened really quickly, and I'm okay if people think that. My mom auditioned for my dad's band when they were teenagers, and when they were in their twenties they got married. Then they pretty much had all musical children. I swear I came out of the womb singing, so I started first singing in groups with my sisters at the Dutchess County Fair, and then it moved onto me wanting to write songs because I was such a middle child. I wanted something that felt like it was mine. I thought that every artist wrote their own songs.

I remember being young and seeing Kara DioGuardi judging on American Idol, and everyone said she was a big hit songwriter, and I was like, "Wait a minute. This is a thing?" Then I decided that I wanted to write songs for me, but also for other people, and I just went at it. I would write with anybody I could, and then I went to school for music. I've been called back for The X Factor with my sisters, I've been called back for The Voice. I've gone on anything that you can think of that people have tried to do to "make it,” and I've been all the way at the end just to be told that I'm too nervous, or they have too many brunettes, or that I had really nice legs and to come back next year. Weird things have always happened.

I feel like Songland was a [product of] years of me knowing when to say yes and when to say no. I'm so happy I said yes to that. I've been working on writing songs for so long, I've been working on my voice for so long, and I've got my heart broken so many times. It felt really cool to be on a TV show just being myself and telling my own story. So not necessarily overnight—more like since the womb, but I'll take it.

You said that you fully intended on giving "Pill for This" away to another artist, but Charlie Puth encouraged you to keep it for yourself on Songland, and it ended up becoming the lead single from The Medicine. How has your relationship with that song changed since you first wrote it?

It was always a really, really emotional song for me because it was very personal, and I tried to give it away. I pitched it to everybody. It sat in my Dropbox for almost a year, and then Songland said they wanted it. I remember being somewhat torn because I still had such an emotional attachment to the song, and I don't get like that. I spent that week leading up to the show detaching myself and saying, "This song's going to help so many people. Let it go," because I believe my job as a writer, even if I am singing the song, is to reach as many people as I can who need to hear it.

I think I have a love for that song in such a different way now, but I'm really happy I tried and exhausted every option because the way that it came back to me is ultimately what changed my life. "Pill for This" has such a sentimental meaning to me, but I'm not sad when I sing it anymore. I'm so thankful for that person, for that experience, for that song, and for the way that it came back. "Pill for This" is gonna always be my favorite child.

You also went to Berklee College of Music with Charlie Puth. Have you guys stayed connected at all post-Songland?

Yeah, once in a blue we'll reach out to each other. When the episode came out I actually got the most beautiful message from him. He said he hoped when he heard “Pill for This,” that by not taking it, seeing how incredible I was at telling my own story, and losing Songland, his fans would almost get mad at him, follow me and help me build my career. Then he texted me and said, "I can't believe it worked." I was like, "You're so sweet," and he said, "Take this seriously. Get to work. Record as much as you can, write as much as you can, and get ready because you're getting a platform to do whatever you want.” I've been taking that to heart, and I just appreciate that so much. He's just such a kind person.

What was the inspiration behind opening track on the EP, "Unfinished"?

It actually has a dual meaning. I'm a hardcore friend, and it was the first time that I had to deal with losing a friend. I remember saying all the time that I'm not gonna get the answer that I want, so we just need to be unfinished. Maybe I'll see him, maybe I won't, and it's fine. Then "Pill for This" was written, and I knew Songland was coming out. I got this kind of panic like, "Oh my God, what's gonna happen if the ex I wrote 'Pill for This"'about sees this? What's he gonna feel?" I thought about it, and I just went back to that feeling.

I really wanted to open the EP with that song; about the lack of closure because I've felt that with losing a friend, and I've felt that still about that ex. I think no matter how much we get whatever we think is closure, we always want more, and for me that story will always be unfinished. I'll never know if he watched the show, if he’s heard the song, if he hates me, if he's mad at me for it, or if he forgives me. I've forgiven him, and I've realized that I have to move forward. That's where that song really came from. It's such a special song to me. I love it so much.

The EP focuses a lot on your mental health, especially in the context of relationships. Is it difficult to remain so vulnerable in your songwriting knowing you have a large audience now?

I think it's become easier, which is so strange. I have always put unnecessary pressure on myself and these newfound—I almost don't want to say "fans" because I just feel like they're my friends. They're people that I may never meet, but I hug them musically when they drive, or if they go through something. That's how I feel, and that's always what music was for me, so to be that for somebody is still something that I get emotional talking about. I'm just so thankful, but seeing people react in such a way to me being vulnerable has given me strength to be more vulnerable.

I feel stronger than ever because of the support I have from people saying that that's what they need to hear, and I take that responsibility so much to heart because I want to make sure that I keep it honest, so I'll just forever be keeping it real 'cause that's what they want, and that's what seems to be what works. I'm very thankful for that.

You also recently co-wrote Dixie D'Amelio's debut single "Be Happy," which is climbing up the charts thanks to a remix with blackbear and Lil Mosey. How did that track come together, and have you had the chance to connect with Dixie?

It's so crazy. When I first moved to L.A. in 2017, I went to HomeGoods and bought one of those little cheap, cheesy "Live, laugh, love" type signs—people call them Karen signs. I got one that says “Be Happy” and put it on my desk, and then I was in a full-on bad week and faced it down. When I moved into my new apartment in 2018, I picked it back up and wrote in my phone, "Sometimes I don't wanna be happy. Don't hold it against me," and then I called two friends of mine, one of them [who] I wrote "Broken" with. I held onto that concept. I just felt like it was so strong, and I love thinking about the people that need it, and I needed it at the time.

We wrote the song, cosmically enough, June 26, 2019, and Dixie released it June 26, 2020. She never takes credit for writing it. She's so good about that, and she just says, "It was the song that I picked because I resonated with it the most, being with a pandemic, dealing with this newfound fame, feeling like I had to always put my life out there, and sometimes I just don't wanna be happy, and that's okay.” I've always believed happy people can write sad songs, so for me "Be Happy" was such a therapeutic moment.

I have yet to meet Dixie. We were supposed to write in person, but the pandemic changed that. We're pitching songs to her for now, but we will write eventually. She sent me black roses, a thank you card and a video saying thank you for the song. She followed me on Instagram, which got me a lot of little "Charli Dixie Forever" fans following me, which is cool, but I just really have nothing but kind things to say about her. I'm in awe of how she handles herself as a 19-year-old newfound pop star. It's incredible, and that song is changing my life and so many people's. I'm so thankful for that.

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