Jaelee Roberts Plants Firm Roots with Debut Album, ‘Something You Didn’t Count On’

Contrary to what her debut album title may say, Jaelee Roberts’ journey to and subsequent success in music is something that surely could have been counted on. Having grown up the daughter of two music industry professionals, Roberts spent her youth backstage at the Grand Ole Opry and competing in (and winning) several singing and fiddling competitions. As she entered her teens, she started writing songs, and as she exited her teens, she took a record deal with a premiere Bluegrass label with her.

The record that her deal spawned, Something You Didn’t Count On, solidified Roberts as one of the brightest young Bluegrass artists and songwriters. Already with an IBMA Award under her belt, the future looks bright for Roberts, who also performs as a member of Bluegrass quintet Sister Sadie.

We chatted with Roberts all about her musical roots, Something You Didn’t Count On, earning praise from and singing with legendary artists, performing on the Opry and more!

Image by Before Charleston Photography

Pro Country: You grew up in Nashville in a musical family and were immersed from an early age. What was it like to be so surrounded with music so early in your life and to have those experiences?

Jaelee Roberts: It was amazing! It paved the way for what I’ve wanted to do for my whole life. I feel so blessed to have gotten to grow up, not just on the music side of things, but on the business side of things too. I’ve gotten to see the music side both on stage and backstage, and the business side of things because my mom is a booking agent and manager. It really showed me that music was something I wanted to do for the rest of my life. I’ve seen that it can be hard, but it’s worth it to me, because I’ve seen both of my parents do it and love it so much. They passed that love to me, and I’m really blessed to have made so many musical friends growing up and to have grown up in the industry.

PC: With those early musical experiences, did it seem inevitable that you would catch the music bug yourself and that would be a path you would follow yourself?

JR: It did, but at the same time, I always say that some kids’ parents kind of push them to do different things, but my parents never pushed me to do this. They encouraged me to do what I want to do, and at four years-old, I was showing interest in wanting to play the fiddle, so they of course went with it [laughs]. I was for sure going to catch the music bug, and I’m glad that I did. They’ve been my biggest encouragers and supporters, and I’m so thankful for that.

PC: When did that early interest and introduction into music translate into realizing you could actually pursue music as a career yourself?

JR: I grew up singing in church and doing contests. I did fiddle contests, singing contests, and even clogging contests [laughs]. I grew up going to Bluegrass festivals that my dad’s band, The Grascals, was playing. I’d watch him go on stage and have the best time, and they would get me up and sing with them; I think the first time I sang with them, I was seven or eight years old. It was to a big crowd, and I loved it! Around 13, I started becoming interested in songwriting and guitar playing. I realized those were things I wanted to do as a career. That’s when I was old enough to realize that this was it.

PC: You released your debut single, “All My Tears,” in 2019, which earned praise from Patty Loveless. What was it like to have a legend of that stature praising your song, especially given that it was your debut release?

JR: Honestly, I was over the moon speechless! I’m a huge, huge Patty Loveless fan, and when I saw that quote from her, I’m pretty sure I cried [laughs]. I thought there was no way it was real. I can’t even express how grateful I am for those kind words.

PC: In the midst of the pandemic, you signed with Mountain Home Music, becoming labelmates with Bluegrass royalty like Balsam Range and The Grascals. What did it mean to you to have the belief from Mountain Home to join a roster with their level of collective talent, and to become labelmates with your dad?

JR: It was so cool! I was 19 when they signed me, and I was in shock. I’m so grateful to them for taking a chance on a 19 year-old girl who had dreamed of having a solo album and a music career. The whole experience has been amazing. Getting to immediately start thinking about songs to record and getting to immerse myself in the album and record label experience was so amazing. Every person that’s on this label is so talented and are absolute heroes of mine, and I still can’t believe I get to be on the label and share that with them. You mentioned Balsam Range, and their bass player, Tim Surrett, is my producer. That was really cool too! I’m so thankful for all of it.

PC: You released your debut single for Mountain Home, “Something You Didn’t Count On,” in February of last year. How encouraging was the strong reception out of the gate, and what drew you and your team to have it serve as the title track for your debut album?

JR: I had said from the beginning that I wanted the album title to be one of my song titles or a line from one of my songs. We were all sitting around thinking about it, and I said, “What if the album was called ‘Something You Didn’t Count On’,” because I’ve been around the music industry because of my parents, but the album was like “here it is! You didn’t count on it, but here it is” [laughs]. It has nothing to do with the actual song, but the album is my baby, and that song is one of the freshest songs that me and my friend, Theo MacMillan wrote, and I just thought it would make a great title, and we went for it!

The response was shocking! With any artist, you never really know how people are going to receive your music. It’s truly nervewracking, but it’s super exciting too. When I saw people were talking about it and requesting it on radio stations, it excited me and makes me want to do more and more. I’m so glad that people are loving this music that comes from my heart. I hope they can feel something from it that they want to feel. I love writing songs that can mean different things for different people. I’m grateful for anyone who’s given it a chance!

PC: “Sad Songs” has been a solid performer for you since the album’s release, and was written by Chris Harris, Josh Matheny and Robbie Melton. How did the song come to you and what was it about the song that drew you to add it to the album?

JR: Cory Piatt is one of my favorite people and mandolin player. He recorded it years and years ago. My mom and I were listening through music, and I had almost all of the songs picked out for the record. My mom brought this song to my attention, and I was like, “Wow! This is a song that 100% screams ‘me.’” I sat down with my guitar and started strumming along with it and singing it, and knew it was a 100% yes. We went to the studio in North Carolina and everybody was on board. It turned out better than I could have imagined. I love that song! The writing is insane on it.

PC: Something You Didn’t Count On features a cover of Fleetwood Mac’s “Landslide.” What drew you to add the song to the record and how much did you enjoy putting your own touch on such a legendary song?

JR: I absolutely loved it! I love Fleetwood Mac and Stevie Nicks. That song has always been a song that I’ve always revisited. If I’m driving in my car and I want to hear a song, “Landslide” is usually in the mix [laughs]. My producer, Tim, brought the idea to me. He said that everybody loves that song, so he suggested trying it. We did it, and I knew it would work. We put it together in an acousticy way, and then we had Vince Gill sing harmonies on it. I will never forget when I got the rough mix back. When he sent back his vocals, I was driving in the Walmart parking lot, and I had to park my car because I started sobbing [laughs]. Vince Gill is one of my all-time biggest heroes, and to hear him singing with me on such an iconic song was crazy.

PC: “Lie to Me” is our favorite song on Something You Didn’t Count On, and is a song you wrote with Jerry Salley and Kelli Kingery. Can you take us in the room and tell us how the song came together?

JR: I was at Jerry Salley and Donna Ulisse’s songwriting workshop, Little House Workshop. Me, Jerry and Kelli all went in a room and were passing around hooks. I believe I had the idea of “Lie to Me,” and we went with it. We each had our guitars and we each started strumming melodies. Within about an hour and a half, we had the song written! It’s about a relationship that’s coming to an end, but you don’t want to admit it, so you’re desperately asking the other person to lie to you because you don’t want to know the truth about them leaving. We were all in our feelings when we wrote it, and a nice sad song came out of the session [laughs].

PC: What do you hope listeners take away from Something You Didn’t Count On after listening all the way through?

JR: I hope that the songs I wrote mean something different to everybody. I hope they can feel it in their own way. I hope they get positive vibes from the album, and I hope they love it. I hope it’s music that they want to keep hearing, because I would love to keep giving music for as long as I live.

PC:  In September of 2021, you received the IBMA Momentum Vocalist of the Year award. What do awards and recognition like that from within the Bluegrass industry mean to you, especially so early in your career?

JR: It’s shocking! I was not expecting to receive that award. Everybody in the category with me was so amazing. I love all of those women. When they called my name, I think I went numb [laughs]. I walked onto the stage and I was rushing to thank everybody, because in my mind, there was just no way that it was actually happening. I can’t thank everyone enough who has continued to support me and my music. To this day, I can’t believe it.

PC:  In December of 2020, you auditioned live on stage at the Grand Ole Opry for Sister Sadie. As someone who has spent your early years backstage at the Opry, what did it mean to you to stand in the circle and perform on that stage?

JR: Goodness, that was crazy. I remember Deanie Richardson, the fiddle player, calling me. I had already auditioned, but they wanted to do live auditions for everyone who had auditioned. It was difficult because Covid was happening, but she said that that my live audition would be December 5th at the Opry, and asked if I would be okay with that. I said, “Wow, I’m definitely okay with that!” [laughs]. I was very used to the backstage of the Opry, but it was a completely different feeling walking around back there knowing I was going to stepping into the circle. When it happened, I remember my own voice hitting my ears. It hit me that I was standing in the circle, on the Opry stage, where quite literally all of my heroes have stood and sang. It was all I could do to keep from crying. We finished and I went to the backstage dressing room and I remember sitting down on the couch and crying. I was like, “There is no way that that just happened.” I was so grateful to them for even giving me that opportunity. Even recently, every time you play the Opry, it’s just like the first time. The feeling never goes away. Recently we played, and I got to play “Something You Didn’t Count On.” As I was singing, I realized I was singing a song that I had written. Then it hit me extra hard [laughs].

PC: About two months later, you were officially announced as a member of Sister Sadie. How much do you enjoy collaborating with the band and combining your collective talents?

JR: It’s a feeling like no other! I’ve looked up to Sister Sadie ever since they came out years ago. I’ve known all of these ladies for my whole life. They’re absolute heroes of mine. I’ve learned so much just standing on stage with them and getting to collaborate with them. We’re starting a new record and getting to write together and put ideas together about songs we want to record. It’s absolutely amazing! We’re so excited about the new music that’s going to be coming out. I’ll never take this opportunity for granted.

PC: Along with working on a new Sister Sadie album, what do you have planned for 2023?

JR: We’ll definitely have the Sister Sadie album, and we’ll be playing a bunch! I’m hoping to play some solo gigs as well. I’m going to keep writing as much as possible. I’m in college right now as a songwriting major, and I’ll be graduating this year. I’ll probably be starting a new solo album too. There’s lots of cool stuff! 

PC: Is there anything you’d like to add?

JR: If you want to find me and where I’m at, you can go to the Sister Sadie website or my website!

Image by Sandlin Gaither

*Feature image by Sandlin Gaither

**Jaelee’s music is featured on The Best of Pro Country playlist!**


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