Jessi Alexander never intended to move to Nashville to become a songwriter — she simply wanted to make a living in the music business anyway she could. The West Tennessee native vividly remembers being enthralled by music as a young girl. Long before she had hits by Blake Shelton, Lee Brice and Miley Cyrus, she began playing her grandparents’ piano and taught herself Elvis Presley’s “Love Me Tender” by ear around the age of nine. By the time she was 11, Alexander began to dissect lyrics and rhyme schemes from the sheet music her family bought her.
“I would look at the top of the pages and I would see a song like Patsy Cline’s ‘Crazy,’ but I’d see in little writing at the very top ‘written by Willie Nelson’ or ‘written by Harlan Howard.’ I can remember putting it together around that age, ‘Oh, there’s people that write songs,’” she tells Billboard. “I would take songs that were already written and rewrite the lyrics. Then, more importantly, I really started my education as a songwriter because I started at a very young age to dissect lyrics and dissect rhyme schemes or emotions and really was not normal for an everyday average 10- or 11-year-old.”
Now the mother to an 11-year-old, Alexander laughs as she realizes this isn’t how her daughter is spending her free time. This passion for music and songwriting eventually led Alexander to Music City. While attending college at Middle Tennessee State University and pursuing a social work major, Alexander would travel to Nashville whenever she could in hopes of getting a job in the music industry. She’d often spend her nights at the Bluebird Café, 3rd & Lindsley and 12th & Porter making connections.
“I was trying to sing; I was trying to work. I was working with the car auction, at Subway. I had a ton of jobs. When I moved here in ’99, I just wanted to use my voice or my writing,” she says. “I’m so fortunate that it worked out for me. So I quit college and just made my way.”
Alexander’s first day in Nashville included an audition at SIR Nashville to be a backup singer for Reba McEntire. While she didn’t get that gig, she met another artist — Matt King — who was signed to Atlantic Records and needed a backup singer. Her second day in town she played the Grand Ole Opry, and her third day she was on the road.
King began sharing her songs with his publishers at Warner Chappell Music, where Alexander garnered her first publishing deal in 2000. While Alexander’s early days in Nashville seem like an instant success, she is quick to caution that it’s “not all a Cinderella story.” Shortly after she got her job with King, he lost his record deal. Then all the people who signed her at Warner Chappell got fired and she lost her first publishing deal.
“If there’s a theme to my whole career, it’s when you think you’re settled, you have your team, the team can change. So I’ve had to learn a lot of self-resilience and just try to just keep my head above water, keep focused and keep my head down working,” she says, admitting that she never had a fallback plan.
Alexander would eventually sign to Columbia Records, who released her debut album, Honeysuckle Sweet, in 2005. By the following year she was dropped from the label. By her mid 20s, Alexander admits that she had given up on the idea of being an artist. “I knew I wanted to be a songwriter, and there were those years where I was just writing songs, trying to get them placed,” she recalls.
“My [now] husband, Jon Randall, had just won song of the year for ‘Whiskey Lullaby.’ I’m thinking, ‘Gosh, he’s killing it and I’m washed up and not getting anything accomplished over here. Maybe I’m supposed to marry him, and I’ll be a mom,” she says. “It was through that period of time, the frustration I was going through, I was writing a lot of stuff about that. And that’s when me and John Mabe wrote ‘The Climb’ for Miley Cyrus.”
Alexander admits that writing “The Climb” was therapy for her and Mabe. The pair penned the song in 2008, and Cyrus released it in 2009, the same week Alexander gave birth to her daughter. “I had this bizarre twist of fate where I was just about to give up, and bam! Not only one of my dreams came true, but beyond my wildest dreams,” she says of the song that remained at No. 1 for 15 weeks on the Adult Contemporary chart and saw crossover success in five formats, including pop, country, Christian, Adult Contemporary and Adult Top 40.
“I also have the biggest job I’ve never done, which is parenthood and motherhood. I’m learning how to swaddle a baby while Miley is playing at the inauguration of President Obama.,” she adds. “It couldn’t have gotten any weirder. That was my first major hit — a game changer — and opened so many doors and really gave me that confidence of, ‘Yeah, I’m a songwriter.’”
Lyrics within “The Climb” that still hold personal meaning to Alexander include “Ain’t about how fast I get there/ Ain’t about what’s waiting on the other side.” While the songwriter admits the lines sound “so cliché,” it’s those very lyrics penned in frustration that have become a mantra for her life.
“It’s so simple. I still get caught up, just like we all do, with what someone else is doing or how did they get there faster and why am I not where I think I should be? But it’s almost like God gave me those words to be some kind of mantra to myself,” she says. “Even I sometimes have to remember, ‘Slow down. This is your journey. It’s not someone else’s journey. And if you rush and get there too fast, what would the whole journey be like if you got it all right away?’ I really try to live those words.”
While “The Climb” put Alexander on the map as a songwriter, she wasn’t a pop writer. Now, she had to convince the industry that she was actually a country songwriter. “There were the years of me trying to figure out, ‘OK, how do I reinvent myself?’ Again, I’m not a pop writer. When we wrote ‘I Drive Your Truck,’ that was … if I had any doubt that I was supposed to be a songwriter, having ‘I Drive Your Truck’ was the major turning point. ‘The Climb’ wasn’t luck. This is my purpose; this is what I’m supposed to be doing.”
Brice’s “I Drive Your Truck” holds even deeper meaning for Alexander. Written with Connie Harrington and Jimmy Yeary, Alexander said she was thinking of her late mother and grandfather while penning the future ACM and CMA award-winning song of the year.
“I’ll never forget when we came up with the line in the room, ‘Mom asked me this morning if I’d been by your grave/ But that flag and stone ain’t where I feel you anyway.’ That line right there hits home for a lot of people in dealing with grief,” she says. “For years I never went to my mom’s grave and I’m sure that’s why that line cropped up, because it’s so personal to me. I really just knew I had to write about it one day and it never really presented itself. So when Connie Harrington brought that idea into me, I literally felt like someone had shot a laser gun through my body because it was like, ‘Oh my God, this is it. This is it!’”
While Alexander has made her living for the better part of the past decade writing songs for other people, there were several songs she penned in 2017 that sounded distinctly for her. When she got into the studio in December 2017 and recorded four of the more personal tunes that would be featured on Decatur County Red, she says something in her opened. The following December, she returned to the studio, and as soon as she recorded “Mama Drank,” she knew she had a record.
On Friday (March 27), Alexander will release her third studio album, Decatur County Red. The deeply personal project showcases the singer-songwriter’s musical influences alongside vivid detail, stunning vocals and ace musicianship. “All the songs are a really good representation of who I am, but the title track [is] autobiographical. Those words — every single word — is true. It doesn’t just encapsulate the music that I grew up around, it also encapsulates the people that I was raised around,” she says. “I hope that when people hear that they feel West Tennessee, they feel the people I was raised around, things I saw, the music I heard, the food I tasted. I feel like all the songs do a little bit of that, but that one especially is so me.”
Additional highlights include “Damn Country Music” and “How I’m Going Out,” the latter of which was previously recorded by Dierks Bentley. “That was on Dierks Bentley’s last record, so it’s really cool to do my own version of it. That song is really personal. I mean, they’re all personal ones, every single one, but it was something I’d been working on quite a while after our friend and songwriter Andrew Dorff passed away,” she says. “I’ll never forget. JR was really upset one night about it. It just poured out. This record is the pouring out of a lot of emotions for me. Good ones, bad ones, funny ones, silly ones, sexy ones. Truly every song has some ingredients [for] a sad or a fun night.”
“Damn Country Music,” meanwhile, tells Alexander’s rocky journey to becoming a revered country songwriter in Nashville amassing cuts by Blake Shelton (“Drink On It,” “Turnin’ Me On”), Reba McEntire (“When Love Gets a Hold on You”) and Trisha Yearwood (“PrizeFighter”), among others.
“I didn’t think I could do this. I didn’t have any idea. And no one remotely in my peripheral had ever done anything like this. So it’s really just total reckless abandonment and literally living paycheck to paycheck, working three jobs. And that’s what ‘Damn Country Music’ really is about,” she says. “I will be writing songs, whether they’re playing them or not. I’m born to do this.
“If you want to keep making a living making music, you have to change with the times. And that’s probably why I partly made a record; just keeping myself creative, keeping my energy, changing it up a little bit. It’s been really, really fun. Hopefully when someone hears [the album], they get a strong sense of who I am.”