Caitlyn Smith: Student of Songs

It all started when she was 8 years old, sitting in front of her boombox listening to the cassette tape of Alison Krauss’ retrospective album, Now That I’ve Found You: A Collection, flipping it over and over and studying the lyrics with a question burning in her mind: “How did someone write these incredible songs?” 

“When I listened to that record, it transported me to all of these feelings that I didn’t necessarily understand or have,” Caitlyn Smith recalls to American Songwriter about the album that sparked her interest in music. “It just took me to this magical place. It struck me as ‘I don’t know what it is, but it’s special.’” 

Smith took the “masterclass songwriting” she learned by listening to Krauss’ music and applied it to her own songwriting, penning her first country song, “It Felt Like Magic,” at the mere age of 8, foreshadowing her future career as a hit songwriter. 

Smith was raised in Cannon Falls, Minnesota, and moved to Nashville in 2009 where she became a staff songwriter at hit songwriter Brett James’ publishing company, Cornman Music. She quickly established herself as a sharp lyricist. Jason Aldean and Rascal Flatts were among the major country artists who cut her songs early on, Smith writing “It Ain’t Easy” on Aldean’s chart-topping 2010 album, My Kinda Party that’s been certified 4x platinum by the RIAA, and “Let it Hurt” that Rascal Flatts recorded for their 2012 album, Changed, that hit No. 3 on the Billboard 200. 

She experienced a true full-circle moment when she found herself in the room with legendary songwriter Don Schlitz, who co-wrote one of the most famous country songs, “When You Say Nothing at All.” Originally recorded by Keith Whitley, it was later turned into an international hit by Krauss and has since become one of her signature songs. It was one of the many songs Smith had on repeat while listening to Now That I’ve Found You. Schlitz became a songwriting mentor for Smith, imparting an important piece of wisdom. 

“One thing that Don taught me when I first moved to town was to become a student of songs,” she explains. “I was doing that as a kid not even realizing it, but then moving here to Nashville, I went back to those records with so much more intention. Whenever I feel uninspired or empty as a writer, the best thing that I can do is become that student again and go back and dig through records and try and get that inspiration.” 

Schlitz’s words taught her a valuable lesson: “There’s always something to write about.” Smith admits that in her early days of writing, she’d often wait for inspiration to strike, going through dry spells where she wouldn’t pick up a writing pen. But Schlitz’s advice taught her to keep moving forward. “If you can’t think of anything to write about, you’re just not paying attention,” Smith says of how she interpreted Schlitz’s advice. “It just is a matter of opening your eyes and your heart and mind.” Smith took his words to heart, committing to continually sitting down and working at songwriting until she perfected the craft. “You’re going to write bad songs, but you’ve got to write the bad songs to get to the good songs,” she acknowledges. 

Smith found the magic once again when she and Schlitz had a songwriting appointment the week after Schlitz was inducted into the Songwriters Hall of Fame in 2012. He was inducted by Kenny Rogers as the writer of “The Gambler.” During the ceremony, Rogers leaned over to him and requested that Schlitz write a song for him based on the title, “You Can’t Make Old Friends.” Schlitz pitched the idea to Smith, the pair writing the tender-hearted song that celebrates an enduring friendship. Months later, they found out that not only did Rogers record the song, but he invited his longtime friend and beloved collaborator Dolly Parton to join him in celebration of making music together for 30 years. It was the last duet they recorded together before Rogers died in 2020. Smith says the lines, How will I sing when you are gone? / ‘Cause it won’t sound the same, are her favorites in the song. 

“Every time I sing that live, I still get a little choked up, thinking of how good of friends Kenny and Dolly were and how now she’s going on singing without him, and it won’t ever be the same,” Smith reflects. “I have a bucket list of artists that I would love to have record my music, but they’re so iconic that it was not even on the list. The fact that that even happened, it’s so mind-blowing, I still can’t believe it.”

Rogers and Parton aren’t the only superstar names who have been drawn to Smith’s songwriting. Meghan Trainor and John Legend’s multi-platinum duet “Like I’m Gonna Lose You,” “Tacoma” by Garth Brooks, and “High” and “Island” by Miley Cyrus are among Smith’s other heavy-hitting cuts. Smith co-wrote “Like I’m Gonna Lose You” with Trainor and Justin Weaver, the song charting in multiple countries, reaching the Top 10 on the Billboard Hot 100. Smith and her husband, Rollie Gaalswyk, are the writers behind The Voice winner Cassadee Pope’s debut country single, “Wasting All These Tears,” which reached No. 10 on the Billboard Country Airplay chart and has been certified platinum by the RIAA. 

Smith’s wide-ranging list of cuts demonstrates her flexibility as a songwriter, her intentionally written words allowing her to fit into any genre. When stepping into the room with another artist, Smith compares her job to that of a therapist, creating an atmosphere where the artist feels comfortable to open up and share their story. “My job then turns into digging around in their heart and head trying to pull out what it is they want to say,” she says. “If I can get in the room and try and tell some truth, it’s usually the best-case scenario.” 

Cyrus recorded “High” as a deep cut off her 2020 album, Plastic Hearts. Smith and her co-writers had written the song that got passed around Nashville before it landed in the hands of Cyrus’ producer, Mark Ronson, who presented it to the superstar. Cyrus altered some of the lyrics to fit her personal story, much to Smith’s delight. “When Miley heard the song, she connected with it and loved it,” Smith says. “The beautiful, crazy thing is when I hear her sing that, it feels like it’s her story. I believe all of the words, and it’s so incredible to me when there’s something that I wrote that was so personal, something that was going on in my head space that someone else takes and I’m like, ‘That seems like it’s totally for you.’” 

In the midst of her highly successful songwriting career, Smith stepped out as a solo artist with her 2018 debut album, Starfire, which proved her to be a powerhouse songwriter with a captivating voice. She continued to prove her stamina with her sophomore album Supernova and as well as her new, recently released project, High & Low. 

Smith recorded her own version of “High” for High & Low. She notes that it’s “two different sets of tools” between writing for other artists and herself. Having recorded three studio albums as a solo artist, Smith’s personal songwriting process requires her to “go into my own memories, my heart space and figure out what’s going on inside of there, and what do I want to pull out for a song today?”

With High & Low, Smith is more vulnerable than ever before, dropping the mask she feels she’s been wearing since she moved to Nashville at 23. She admits she’s mastered the facade of making life seem OK even when it wasn’t, a task she calls “exhausting.” The album explores the highs and lows of life, with Smith opening up about her lows in a way she hasn’t before. “In making this record, it was a massive growth season,” she explains. “Digging through my own mental health in the last few years brought me to a place of trying to be more real. I feel in a sense that I was able to hide it in my songs in the past.” 

No longer using her songs as a mask, Smith lets her emotions take the lead on High & Low. She points to the album closer, “The Great Pretender,” as a prime example of letting her guard down through lyrics where she admits to using laughter as a way to hide her pain, confessing to crying in bathroom stalls and telling stories that don’t contain the whole truth. 

“[I’m] really being more intentional about [the idea of] let’s be real about what we’re talking about. I went through some really hard things and I’m sure that people out in the audience or people listening to this record have gone through a lot of these same things and offering space to honor those lows instead of laughing them off or being uncomfortable or afraid of them,” Smith says of how she approached the album. “The vulnerability is showing up more and more in my songs. It’s serving me more and more in the writing room.” 

This also marks the second time Smith has produced her own record, a feat she accomplished with her 2020 album, Supernova. Producing puts even more of the power in Smith’s hands. Citing production as something she had long been curious about, Smith was inspired to start producing during the COVID-19 pandemic, locking herself in her office where she recorded her own demos and cut her vocals, adding a new level of excitement to her creative process. It was yet another way that Smith stretched her capabilities and believed in her voice, a facet she brought with her from Minnesota to Nashville and is reflected in each of her songs. 

“I moved here 13 years ago as a staff songwriter. I just started writing, slinging songs on Music Row,” Smith says, “and I feel like for a lot of years, I played a character where I played what I thought this would be. I would put on a hat every day and say, ‘This is this,’ or ‘This is a country song.’ I was touching the edges of pain, but I was too afraid to actually look at my own pain. 

“There’s a lot of magic that happens in this town and I think songwriting in general is magic. You get into a room and you have no song and then somehow something happens and then there’s a song. I still don’t know how it happens,” she continues with a laugh.“My job is to try and find the words and pull out the emotions and put them in a little three-, four-minute song so that other people can put them in their own lives and do that healing. Are we all ever going to be fully healed? I don’t know the answer, but I’m definitely on the road and I’m a little bit closer than I was yesterday.” 

High & Low was released on April 14. Smith will headline The Great Pretender Tour through June 1. She’ll serve as a supporting act on select dates of Dierks Bentley’s Gravel & Gold Tour in the summer of 2023 and open for George Strait at Hard Rock Live in Hollywood, Florida, on August 2.

Photos by Robert Chavers