Jesus Calling Podcast

Healing the Holes In Our Hearts From Loss: Holly Singletary and Andy Griggs

Holly Singletary: The first year, I felt like was almost like autopilot. You know, I’m good at this mom thing. I love this. I wanted to be a mom forever, so I’ve got the mom thing. But it was like now I’m mending four broken hearts, and how do I do that okay—not just okay, but how do I make them properly grieve because I don’t even know what that looks like. 

Narrator: Welcome to the Jesus Calling Podcast. Grief, death, and loss are an inevitable part of life, though knowing that doesn’t make the pain any easier to bear. Whether you’ve faced unexpected loss time and again, or you’re navigating grief for the first time, the waves of difficulty can be drowning. But the good news is that God can offer us a life raft. Isaiah 57:18–19 says, “I will heal them; I will guide them and restore comfort to Israel’s mourners, creating praise on their lips. Peace, peace, to those far and near.” This week’s guests, Holly Singletary and Andy Griggs, share the holes left in their hearts, and how God has helped heal them, and they share how we can find comfort in the legacies of loved ones passed, and also know deep in our hearts that one day, we will see them again in heaven. 

First up, Holly Singletary, the wife of late country singer Daryle Singletary, reflects on their life together ahead of their wedding anniversary on September 16th: raising their young family, how she navigated his tragic death, and how her children have learned from his faithwalk. 

Holly Singletary: My name is Holly Singletary, mother of four, twin boys and two girls, stay at home mom, but just recently started a podcast and blog. And we live on a farm.

I grew up in a really small town in South Georgia, about thirty, forty-five minutes from Jacksonville, Florida. My whole family is mom, dad—I’m a middle child, so I have an older sister, younger brother. I grew up in kind of your typical small town. You know, everything revolved around church and football. And then I moved away after college, moved to Atlanta, and started working at Emory. And that moved me a little further to Nashville several years later. 

Falling for a Country Star

Daryle and I met. I just remember we kind of hit it off, but [he and his friends] were playing by the campfire and he was singing “I Let Her Lie.” And I remember leaning over to my friend Kelly, and I’m like, “Who sings that?” 

And she’s like, “He does, Holly. He sings it.” 

I obviously said it louder than I thought, because everybody stops. And so I’m just like, “Oh no!” And  everybody gets a good laugh. 

At that point, I just didn’t have a clue [how big of a star he was]. I came home that weekend after meeting Daryle and told my mom and dad that I found the man I was going to marry.

“I came home that weekend after meeting Daryle and told my mom and dad that I found the man I was going to marry.” – Holly Singletary

I always joked with him and said he could be the mayor because anywhere we would go, he reminded me of like that old grandpa who talks to everybody and you just want to talk to him. I would always say, “You’re like the mayor. Everywhere we go, you know someone, or someone wants to talk to you.” And he was so funny, a witty, kind of a practical joker.

I think for us, we really hit it off with the things we had in common, the way we grew up. His family’s very close, and I’m very close to his family as well. They sent him at eighteen to Nashville because he wanted to sing. He knew from early on what he wanted to do. And even hearing his stories, he knew from the age six or seven [what he wanted to do]. And he really didn’t waver from that. He loved Merle Haggard and George Jones from an early age. And so his dad said right away he knew there was something different, he’s like, “We knew.” His mom said he would call on Sunday nights from the payphone over by The Broken Spoke on Trinity Lane and cry to come home. And they wouldn’t let him come home because they knew what he wanted to do. 

A New Stage of Life: Parenting

We were married ten years before we actually had children. I think we both were just enjoying our careers so much. He was a really great dad. He was hands on. He changed diapers. He did the dirty work, too. So it was really sweet to watch, because I think our waiting so long prepared us for a different kind of parenting. I felt like we had a lot more patience, and we appreciated some of the moments maybe that we would not have appreciated earlier on in life.

“It was really sweet to watch [Daryle parent], because our waiting so long prepared us for a different kind of parenting. I felt like we had a lot more patience, and we appreciated some of the moments maybe that we would not have appreciated earlier on in life. – Holly Singletary

Touring never stopped for him. And a lot of times, he would make it back home for Sunday morning and we would go to church. That was our favorite day because Dad came home on that day. And then for the kids, it was the day we would go to dinner after church. It was a treat. 

We worked really good together. We just kind of had a system, you know, but there were times when we would be sad because Dad’s leaving on Thursday and we were bummed, you know. But he would always say, “I get to be with you at home for four days, and a lot of dads don’t get to do that.”

Building a Family of Faith

He definitely took the leadership role, the man of the house, even in the spiritual sense. He would lead us in prayer. We would do devotionals together, and that kind of spilled over into the kids as well. 

We really fit in there with that church in that group [in our town]. We’re still there. The kids and I still go. And they were really such a huge blessing to us when Daryle passed away. Talk about stepping up and stepping in. I’m just very thankful to have that body to kind of carry you. 

We cry together sometimes. We tell stories a lot. And so for us, I feel very blessed to have his music. I saw that really early on with the kids. They have their little iPads and they’re connected to Daryle’s phone. So all of Daryle’s love for music—not just his songs, but all those old songs that he loved, you know, I catch them listening to. [There are videos of Daryle on YouTube]. So we’ll pull up especially the talking videos, we love those because he’ll tell a story and we get to hear his voice. So we talk a lot about that, and how blessed we are to still have that connection, like he’s still here. He’ll always be here. But those are really things I’m thankful for, that we still get to hear that voice and that music and the kids really eat that up. 

I’m just real honest with them, and I feel like for us, that’s really the best way because I want them to feel like they can ask me anything. I don’t want them to ever feel like, “Oh, I don’t want to talk about Dad because it might make you cry.” And so I tell them it’s okay to cry. We have good and bad days, and some days we miss him more, especially on those special days or special moments or just an everyday moment. I’m like, “It’s okay to be sad.” But one thing I tell them is, “It’s not okay to stay there. I don’t want you to stay there. I don’t want that to turn into bitterness and anger and madness.” And so I think we’re kind of more, I guess, a cup half full, not half empty. That’s where gratitude, I feel, comes into place for us. We’re on our third year of [missing him]. I don’t like to say “moving on,” but we’re moving forward.

“It’s okay to cry. We have good and bad days and some days we miss him more, especially on those special days. I [tell the kids], ‘It’s okay to be sad. But I don’t want you to stay there. I don’t want that to turn into bitterness and anger and madness.’” – Holly Singletary

Narrator: To learn more about Holly’s story and her new podcast, Hope With Holly, please visit

Stay tuned to Andy Griggs’ story after a brief message.

Jesus Calling podcast #261 featuring Jesus Listens by Sarah Young

Jesus Listens: a new prayer devotional from Jesus Calling author Sarah Young!

Many of us want to develop a deeper prayer life. In this new 365 day devotional, Jesus Listens, Sarah Young offers daily prayers based on Scripture that will help you experience how intentional prayer can connect you to God and change your heart. Learn more about Jesus Listens and download a free sample at

Narrator: Next up is musician Andy Griggs. Andy has suffered through a life full of crushing moments and devastating heartbreak, including the loss of his father to a brain tumor, his brother’s passing from heart complications at a young age, and the death of one of his dear friends—Holly Singletary’s husband, Daryle. Picking up their baton, Andy jumped into the music industry feet-first, longing to make a difference in the world and desperate to find healing in both the music and their legacies of faith. 

Andy Griggs: I’m Andy Griggs and I make country music. I’m from North Louisiana, a town called West Monroe, Louisiana. But Nashville is my home. I’ve been here a long time. 

So I actually come from that perfect red, white, and blue picnic family where nothing wrong exists. There are no problems, there is no sickness, there’s no death. You know? I grew up as a small kid like that, you know, that all-American family where the world is perfect. 

The first time that my world stopped—you know, we all have those moments where our world is just absolutely stopped and it alters your life. You look back and of course, it alters your life. I think I was nine years old when my daddy was leading the song service in our church on a Sunday morning and just fell out on stage, just absolutely fell out. And, you know, of course everybody ran to him, and he was sent to the hospital. We found out that afternoon, that Sunday afternoon, that he had a brain tumor. So all of a sudden, yeah, that’s when your world starts changing a little bit. 

And he went through remission and went through heavy surgery, heavy radiation, but remission. Then for the next year, all I remember is going to different churches and him sharing his testimony. And I’m not just talking about the state of Louisiana. I mean, we went all over Texas and Arkansas and Georgia and Mississippi, Alabama, some parts of Tennessee. Everybody wanted to hear his story. He was on death’s door with this huge, massive brain tumor. And one day, it was gone. Just one day it was gone. So I remember for a year doing that.  

And then all of a sudden, one day after about a year, year and a half, Daddy got a headache again. And this time it was fast. I remember—by now I’m ten years old—and I remember this look on my mama’s face when she said, “All right, boys, let’s go. Your daddy wants us all to meet him at the doctor’s office, so let’s all go to the doctor’s office.” 

I remember this look on Mama’s face. We went and sat down, and Daddy says, “I want you to know, I have it back. And it’s bigger and stronger than ever before.” 

This time, it didn’t take long. 

So Daddy dying was, you know, my first great big mountain to climb. That’s the story of my Daddy, sweet, sweet, sweet memories. He was a great, great man. I still to this day have people come up to me and tell me how much they think of Daddy and that Daddy still crosses their mind after all of that time. Now, he died in 1983, so, I mean, time flies when you’re talking about the loss of a loved one. Time flies. It really does. 

Legacies don’t die. They don’t die very easily. It takes a long time to see the sunset of a legacy. Everybody’s life is a sunset. That’s a beautiful thing at times. It’s beautiful how God made it.

“Legacies don’t die. They don’t die very easily. It takes a long time to see the sunset of a legacy.” – Andy Griggs

Navigating Grief and Loss

It was me and Mom and Mason, my older brother, we tied our knots that much stronger, leaned on God, didn’t miss a beat with church. Matter of fact, I leaned on church. All of our church family was so good to us and good for us. It’s strange how a good family—you see different families do different things. You see them scatter, you see them change for the worse, sometimes you see them close up. It’s a natural tendency to do all of these things, but it’s so warm to watch a family just go up and just those ties that will never be broken, you know, and that was my family. 

I witnessed that with Daryle Singletary’s family. You know, that was the first thing that I just started praying over that whole family with Daryle, was praying for my own experience, the Bible calls it a hedge [Job 1:10], let that hedge become unbreakable, impenetrable. And the more we hurt, the more we lean on each other and the more that hedge the Bible calls is absolutely impenetrable by the enemy. 

Man, I love that. I love that. And I think that’s how the Holy Spirit moves and that’s how it’s meant to be. It’s our natural tendency to sometimes try to bear things by ourselves. Jesus said, “I’m sending the Comforter.” Man, I love that, “the Comforter.” What does the Comforter do? He ties those binds, He mourns with you, but He builds a hedge that is unbreakable. And I think that happened to me and my mom and my brother. 

I think it is instilled into [humanity] that outside of our Heavenly Father and His sovereignty, the most powerful thing in this universe is my words and my prayer. I think prayer, it changes. It changes the future, it changes everything I’m looking at.

“I think it is instilled into [humanity] that outside of our Heavenly Father and His sovereignty, the most powerful thing in this universe is my words and my prayer. I think prayer, it changes the future, it changes everything I’m looking at.” – Andy Griggs

Jesus taught you to pray. And like Paul, you pray hard and heavy and you meditate. You know, when you hit that spot in prayer, you stay there, and let the Holy Spirit just move within your prayer. That’s a lot easier said than done. But yeah, that’s the way I was praying for Holly and the kids when Daryle died. 

And, you know, the irony of that is my daddy’s name was Daryle. When my daddy died, you know, families upon families, churches upon churches everywhere, we had been given that testimony. Oh, my Lord, the prayer chain was big, you know. So, yeah, we made it fine. It was a difficult time, but we made it fine. 

My brother [and I] growing up became inseparable friends, and at times I’ll see that sisters and brothers, you don’t see it often to where they’re just absolutely inseparable. I know a couple of families like that, but not many. And that was my brother. He was my hero. He took the baton of my daddy’s music. And I didn’t, I was more into hunting and fishing and sports. So my brother, he was the musician. He was the songwriter. He was the singer. As he became an older teenager, he formed a band called God’s Country, the Christian country band, and actually came here to Nashville, recorded an album called Glory Road. I sat on the sidelines and I watched my brother. 

My brother was born with a heart condition, so he didn’t grow up big and strong. My brother was real thin and a little short, and he couldn’t go walk two miles with me out in the woods, that kind of thing. But he was certainly, you know, my daddy was Superman, I lost Superman. And all that kind of shifted over toward the way that I saw my older brother. My older brother became the rock star of my life. So when I lost my brother, you know, that’s not just a world changing, that’s a whole universe changing. 

He died in December, and it was my first year in college. That day, just like brothers, we argued that morning over something stupid. But it’s strange, people ask me what got me into music, and it wasn’t any kind of a dream at all. I’ve never had a musical dream. That wasn’t me. I’ve never dreamed of Nashville or tour buses or singing on the stage or looking people in the eye, looking at crowds. My only way to grieve for my brother was through his songs.

“My only way to grieve for my brother was through his songs.”  – Andy Griggs

I picked up his guitar and learned how to play a D chord. His buddy Flipper taught me how to play a G chord and a C chord. I would sit up at nights, that was the only healing, healthy grieving that I could do was music. And it kept me up at night. So as I was continuing to grieve and just play Mason’s songs, the Holy Spirit was ministering to me through that. I didn’t realize I was falling in love with the music in a new way and in a new aspect, I was falling in love with music. From the eyes of a quarterback, not from the eyes of somebody sitting on the sideline like I’d always loved. My life was changing before my eyes and even came to where I was miserable if I wasn’t playing music. Before long, I learned a Merle Haggard tune. Before long I learned a George Jones tune and started going that way. It never was a dream of mine. I never had a dream of music. I was just trying to get over my brother’s death. That’s all I was trying to do. 

Building a Music Career

So, yeah, 1995 I moved to Nashville and didn’t know a soul outside of two guys, didn’t know a soul. I transferred my Sam’s Club job to here. I just had a few demos here and there. I was already talking to a record label and getting close to signing by the end of ‘97, so I mean, that’s pretty quick.

We went in and recorded that album and Brett Jones and I wrote, “You Will Never Be Lonely,” and we decided that would be the first single. So we released it in December of ‘98 on Pearl Harbor Day. We released “You Won’t Ever Be Lonely,” December of ‘98. So I watched it become a number one, you know, right out of the box. Number one hit by springtime.

Now, I’m in that generation where I saw Nashville change. I saw music change, I saw the whole mentality change. The writing changed, the dreams changed, the pursuit changed, the intent changed, everything changed. Songwriting to me is a strawberry, but it’s also a thorn in my shoe. You know, the most aggravating thing is when you can’t get something out, oh, but how sweet it is when it does. Ah now that’s rewarding, that’s very rewarding. 

I first met Singletary right when I started, he was a step ahead of me. So when we first met, it was here in Nashville, and we respected each other’s singing. I remember us talking about that, and we would see each other here and there. I always thought Daryle had such a smooth, big voice. Having a friend in this industry that is a friend to be a friend—I’ve got a million friends in music and all of us artists, it’s a small family, but we don’t call each other and say, “How are you doing? You’ve been on my mind.” That doesn’t happen in this town. It doesn’t happen. But Daryle and I were that way. I would confide in him and he would confide in me. As much as I miss Daryle’s singing—and of course I do, there’s four songs I still can’t sing because I miss his harmony on it—but I miss his friendship because we did become that David and Jonathan spiritually, iron sharpens iron. 

I can honestly say that out of my few spiritual brothers that answer to, Daryle was one of them. He really was, and I was one of his. We would talk about tithing, we would talk about our problems, talk about our victories. We’d talk about our valleys. We would sit down and pray together, music didn’t have anything to do with that. I miss that because, again, that doesn’t happen in this town. It was a very special friendship I had with Daryle. 

I have learned that when you grieve through the Spirit, there’s a healing that takes place. And it’s supernatural. It’s godly. And it’s like stepping into a hot tub and just releasing everything. And not only are you made whole again, but you’re bigger, you’re better, and you’re stronger because of the right way of grieving through the Holy Spirit. You don’t just get through the valley with Him. You reach the mountaintop with Him and you scream “Hallelujah” and you scream “Victory,” in a way that you never, never thought you would.

“I have learned that when you grieve through the Spirit, there’s a healing that takes place. And it’s supernatural. It’s godly.” – Andy Griggs

I’ve seen people who have lost people that you think would be the death of them. And they get through it. They get through it, through the Holy Spirit, through the Comforter. I think that’s such a great, great thing that as a true believer in Christ, I think that is one of our biggest assets in all of life is having that Comforter with us, and that gets me through the valleys.

“As a true believer in Christ, I think that is one of our biggest assets in all of life is having that Comforter with us, and that gets me through the valleys.” – Andy Griggs

Narrator: Andy shares a passage from Jesus Calling, February 3rd, as he closes out our time with us today. 


I am with you and for you. You face nothing alone—nothing! When you feel anxious, know that you are focusing on the visible world and leaving Me out of the picture. The remedy is simple: Fix your eyes not on what is seen, but on what is unseen. Verbalize your trust in Me, the Living One who sees you always. I will get you safely through this day and all your days. But you can find Me only in the present. Each day is a precious gift from My Father. How ridiculous to grasp for future gifts when today’s is set before you! Receive today’s gift gratefully, unwrapping it tenderly and delving into its depths. As you savor this gift, you find Me.

Narrator: To learn more about Andy Griggs and his music, please visit  

If you’d like to hear more stories about navigating grief, check out our interview with Eddie Montgomery

Narrator: Next time on the Jesus Calling Podcast, we speak with music artist Travis Tritt, who shares how God is in our past, present, and future. 

Travis Tritt: I got saved when I was six years old at a Christmas play that our church did. And it was so moving to me, and it was something I always grew up with and always had as a foundation. Even though there were times when I strayed way away from it, it was always something that was in the back of my mind, in the back of my heart, even during those times. Every time that I ever had any kind of issues or worries or concerns or whatever it might be, I found that I could unload those things in prayer, and that really, really has been something that’s been special to me throughout my entire life.

Leave a Reply

Your email address will not be published. Required fields are marked *