Jessi Alexander on Her Climb in Nashville From Fledgling Artist to Blockbuster Country Songwriter: ‘I Love the Thrill of the Chase’

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When you look at the lists of the most reliable hit songwriters in the country music business, you can do a lot of scrolling to find more than a couple of female names popping up. Jessi Alexander is doing her part to make sure that not every Music Row writers’ room is a boys’ club, [...]

When you look at the lists of the most reliable hit songwriters in the country music business, you can do a lot of scrolling to find more than a couple of female names popping up. Jessi Alexander is doing her part to make sure that not every Music Row writers’ room is a boys’ club, just the vast majority of them. Her list of No.

1s includes such smashes from the last 15 years as Lee Brice’s “I Drive Your Truck,” Blake Shelton’s “Mine Would Be You” and “Drink on It,” Morgan Wallen’s “Don’t Think Jesus” and Luke Combs’ “Twisters” hit “Ain’t No Love in Oklahoma.” If that list seems dominated by male artists — as any list of country No. 1s is — it’s worth noting that Alexander has also written indelible songs by many of the genre’s leading ladies, from her friend Miranda Lambert’s “Things That Break” to Megan Moroney’s modern standard, “No Caller ID.



” Prior to her being celebrated as one of Nashville’s preeminent songwriters at Variety ‘s Power of Women: Nashville event, we caught up with Alexander via phone from her home in town, which she was about to leave for a full day’s worth of what she calls “blind dates” with other writers in town. She talked about her origins as a Sony Nashville recording artist, breaking through as a hit writer with Miley Cyrus’ “The Climb,” perseverence when there was no success, and occasional stereotyping after there was. She also talked about how glad she was to have landed in this year’s list of all-genre Grammy Songwriter of the Year nominees, alongside her friend Jessie Jo Dillon, who is also being honored at Variety ‘s event.

Getting a Grammy nomination for songwriter of the year — and being among the first people to get nominated for that, since the category is still fairly new — must have been a real sign of validation, if you still needed any. Absolutely. I didn’t even know it was a category, so it was very exciting to get that call.

I was in Hawaii for a songwriter festival. Typically, I’m with my family and my kids and I don’t really get to revel as much in things because I’m like, “Oh, now I’ve gotta go to a baseball game” or “Now I’ve gotta go to a track meet.” So it was neat to be in Hawaii and just be like, “Oh my gosh, I just got a Grammy nomination” and literally have a day in the sun with it.

And then to find out that there were three other women nominated, which is crazy, and then one of them being one of my best friends, Jessie Jo Dillon...

We’ve worked a lot together and been there through a lot. So yeah, it was just pretty cool. We’d say what are the odds, both of the big songwriting Nashville Jessis being recognized among the five nominees, if both your reputations didn’t make that not so completely surprising.

.. We call it “Jessi squared.

” You started out with a really wonderful debut album in 2005. And there has been one since then, five years ago, but clearly your own recorded output is on the sporadic side, taking a big back seat to the songwriting. Not everyone can easily make the transition you made, presumably thinking or hoping “I am going to be a star as a recording artist,” and going from that to a songwriter — which, although not maybe a star to the whole world, has made you a star in your community.

Well, it was not an easy transition by any stretch. Because I think people like to categorize people — and I mean, we all do it. I’m guilty of it as well, you know, being like, “Oh, he’s a track guy,” or “Oh, he’s a side man,” or “Oh, she’s a backup singer.

” But if you know my history moving here, I really had a simple goal, and that was just to make a living making music. I didn’t want to work at Subway anymore, or the car auction or all my jobs I had, so I didn’t really seek out any specific profession. I was naturally good at background singing, because I’d been in bands, and I worked at demo singing (along with) songwriting.

So I feel like I’ve just been kind of cruising down with that one motto. And then God has led me where I really think I’m supposed to be, which is kind of the crafter of the song. It’s fun for me, though.

I still get to do a little of everything. I sing on records. I still go out and perform songwriter shows.

And then my favorite job of all of those jobs is songwriting. But at first, I can remember people being like, “So wait a minute, are we here to write for you today?” And I’d be like, “No, we’re not writing for me. We’re writing for Blake Shelton.

” So not only having to convince the guys that I wasn’t writing for myself, but that I wanted to now write for men. That was quite an adjustment, I think, for everyone. And I had to really learn the ropes and really take that one day at a time with grace, and I proved myself pretty quickly.

In 2011, I think, going into 2012, I started just hitting it hard with the guys and getting those cuts and those hits that really made me put a flag in the dirt as a songwriter. In an interview you did recently, you talked about how, when you had a Morgan Wallen single, people were still surprised to see your name on there, because they automaticallhy assume — with good reason, usually — that it’s a 100% male writing room generating any of those songs. Yeah, right? And you have not limited yourself or specialized in any particular type of song.

People associate female writers with more sensitive songs, but you’ve been in there doing every type, including what is traditionally thought of as the male party song. Is there stereotyping that exists where people think, “Well, it’s a woman writer, she’s not gonna want to write this kind of song”? Oh, thank you for acknowledging that. Because that really is probably, of my accomplishments, the one that really means a lot to me.

Because I truly love all kinds of music. I love grew up listening to a lot of different kinds of songwriters. Some of ’em were female songwriters, and a lot of ’em were men.

And there’s nothing that brings me more joy than being the songwriter that you have a little bit of music whiplash, whee you’re like, “Wait a minute. The girl that wrote ‘The Climb’ for Miley Cyrus also wrote a Luke Combs song or a Morgan Wallen song?’ I love being all over the place. But I don’t think I feel that (stereotyping) anymore.

I mean, in the early days, definitely there was a stigma in terms of — like I was saying eaerlier — that transition with the guys when they’re like, “Wait a minute, you’re not gonna sing today? You’re not gonna sing the demo? We’re not gonna pitch this to Carrie Underwood?” And I’m like, “No, we’re gonna write a drinking song about a guy that’s hitting on a girl in a bar.” And I had to earn my stripes there and have to be in the room with the guys and kind of get on their wavelength. And it’s really fun.

I’ve been trying to be more (deliberate) about writing for women, since we have so many great women in country music right now. Last week, I had an idea, and I was convinced that I was gonna write a girl song that day. And it’s so funny how halfway through the write, you could feel the rumbles of the other writer kind of saying, “Ooh, maybe this is a guy song.

” The second we transitioned to it being a male, I felt so much better, and I don’t know what that says to me. I tend to really love the brain of a male. Now that I have sons, it is funny because I tend to relate with them well and I think that there’s a lot of territory you can cover.

But the same with women, you know? And even “The Climb,” people would be shocked to hear, but even when we were writing that one...

We didn’t know it was for Miley when we were writing that song, I thought of a man when I was writing it and even had a male — Jon Mabe, my co-writer — sing the demo. So it’s natural for me to write for men. But I do want to acknowledge how exciting it is right now with Lainey Wilson, Ella Langley, Emily Ann Roberts, Lauren Watkins, Haley Whitters.

I mean, it’s a bonanza of great females, and so I’m loving that. I just went on a writing retreat with Megan Moroney and dove deep with two other women. It was a full girl writer retreat, and that’s so fun.

What is it you love most about what you do? What brings you the most joy? I love the thrill of the chase. Like, today I’ve got two guys on my calendar that that I don’t know; you know, it’s a blind date. I have no idea what we’re gonna do.

I love sitting down (to work). I love the blue-collar aspect of my job. Your readers, they might not know that actually we have these offices that we go to.

We have a calendar. Like, I’m scheduled out till September. I know exactly what I’m doing till September, every day.

I love kind of clocking in ...

I love to get to know new writers, new artists, and then just dissect a song, or craft it from the ground up, and then literally clock out, go pick up my kids and come home and make supper. If you know my upbringing and the people I was raised by, it makes a lot more sense. But I have found a way to make a very creative, artistic life a very kind of normal, day-to-day blue-collar life.

And I think that you mix the kind of stability and day-to-day of my job mixed with the wild magic of what could happen. I mean, today I could write the song that will pay for someone’s college. And that magic happens in a normal office space.

Yeah. Sometimes with no windows and no food. People think we have these kind of elusive, ethereal, go-smoke-weed somewhere jobs in the middle writing songs in the middle of the night, but most people in Nashville are pretty regimented.

You said you’re booked out through September. Speaking naively, how is that possible? That’s five months where you have all your time allotted. Well, I have a wonderful publisher, Jessi Stevenson.

She’s also being honored for the Power of Women impact list, on the business side for women. She does a great job of looking at who’s cutting, who have I worked with in the past, who do I need to get back with..

. I’ll go on the road this summer with Riley Green and work with him. And I’ll take quite a bit of the summer off to be with my kids.

But yeah, I mean, we kind of know [artists’] tour schedules. Other writers have a packed-up schedule, too, so our pluggers or song pitchers, our publishers, get together and they make sure that we’re gonna see each other again. You have a considerable legacy with certain people, like Miranda Lambert, for instance — you’ve been a big part of some of the songs that have made magic in her career.

Yeah, Miranda...

And Connie Harrington’s a great songwriter that I’ve had two No. 1s with, and that now I’m doing the Meg Maroney stuff with. Lainey Wilson is someone that I have had success with, and I continue to want to have that be a part of her legacy.

But yeah, Miranda’s been not only just a great songwriting collaboration, she’s a family friend personally. My kids call her Crazy Aunt Miranda, so she’s a dear part of our lives. It must be gratifying writing for Luke Combs when you know that anything he cuts is going to get, if not a No.

1, then get a lot of attention and be a prominent album track at the very least. And his voice. I get to write for one of the greatest singers on the planet.

A lot of these people I’m mentioning are so great. I mean, when he sang “Ain’t No Love in Oklahoma,” even just the demo that we wanted to send to the producer of the “Twisters” movie, the bare-minimum work tape, was flawless. And getting to write that alongside Jonathan Singleton, who’s from my home — we’re from the same hometown, Jackson, Tennessee — that was extra special to have a No.

1 with him and Luke. It’s been a surreal year, to be honest..

. the last couple of years. Do you have any advice you would give a young woman starting out wanting a career in entertainment in Nashville? Gosh.

Oh man. There’s so much. I’m trying to think what would I tell my kids if they wanted to do this? If you haven’t noticed, I’m pretty big on work ethic; that’s pretty much the cornerstone to everything that I do.

And then there’s passion and there’s talent, and working at your craft. But I mean, just that diligence so that when you get up every day, even if you have nothing going on, you can get something going on. And that’s by going out and meeting people, working on learning an instrument, perfecting your vocals, reading books, research, promoting yourself.

.. I mean, it’s a lot of work and you’ve just gotta apply yourself every day.

And try to outwork . With my job, my whole thought was, “I’m just gonna outwork everybody and I’m not gonna go away, and eventually they’re gonna give me something.” And it took 10 years from them to give me something.

I moved here in ‘99, and I didn’t have my first hit till 2009. So I would just say, you know, if this is truly your passion, then you just have to work like there is no Plan B. With that 2009 milestone being Miley’s “The Climb”? Yeah, yeah.

Quite a first hit. How long does it take from that first hit until you can relax a little and feel like, “OK, people know who I am, I don’t have to push myself quite so hard”? Well, it was funny because after that hit, it felt kind of like it wasn’t a Nashville hit. [The song did make the country chart but made a bigger impact on the Hot 100.

] So I felt like at first the people around here were kind of like, “Oh, so you’re a pop writer.” It was so bizarre, like nothing I ever dreamed of. I didn’t listen to pop music.

I didn’t have kids yet, so I didn’t really know who Hannah Montana was, to a full degree. [The song appeared on the soundtrack for the “Hannah Montana” feature film.] It didn’t knock down as many doors here as you would imagine.

And that’s what I was saying: 2010 to 2011 was when I really had to buckle down and prove myself as a Nashville songwriter. And that was almost harder, because when I had the success of “The Climb,” people started to brand me as “Oh, you must be a pop writer,” or “You must write for franchises, or kids’ music” or whatnot. It definitely was a little bit of a mountain to climb, if you will.

After that, you had your first country No. 1 with Blake’s “Drink On It,” and followed it with Lee Brice’s “I Drive Your Car”; at that point, you’ve got to be kind of in the firmament. That’s right.

I knocked down those doors pretty good. Is there a recent cut you’re proudest of? Or even one going back? There’s so many. I really love the story of getting the song “Don’t Think Jesus” to Morgan Wallen.

It came out a couple years ago, and me and my co-writers, we thought it was kind of a Hail Mary pass when we wrote it. We were trying to write something for Morgan, which can be very daunting, because it’s just hard to write a song for someone to say something so intimate and personal about his spiritual life and his own journey. I felt like it was ambitious.

But we were like, “Maybe no one else has. (tried this), so let’s take a shot at it.” And for Jessi Stevenson to send it to him, and have him immediately feel everything that we felt when we wrote it, go in to cut it, and then release it on Easter, was kind of just the best of all worlds, in terms of my craft.

You know, it’s not just writing something commercial, but writing something meaningful to me that in turn is meaningful to Morgan...

that in turn gets shipped out on Easter Sunday and his fans react to it. It’s just kind of a full circle, because this job, it is a job, but it’s also, for me, a little bit of a mission. It’s a calling.

It’s a purpose. So when I have the songs that aren’t just commercially successful, but are also relatable to people..

. And songs like “I Drive Your Truck,” of course, I’m so proud of, to honor the Gold Star families, or military families. I’m proud of all my babies, but I would say that those two come to mind for sure.

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