Struggle Jennings Breaks Down His Album ‘Monte Carlo’ Track-by-Track

Got the devil on our ass / Praying the angels bring the map / Where we’re headed lord only knows / Some young souls on a lonely road / Had no fathers to follow, Struggle Jennings sings in the chorus of “Monte Carlo,” featured on his latest record of the same name.

Videos by American Songwriter

The song is the perfect curtain opener for the narrative Jennings crafts across the album. The 42-year-old’s lineage is one that boasts generations of musical talent. He is the step-grandson of Waylon Jennings and nephew of Shooter Jennings—which is where he derived his stage name – and his mother, Jennifer Eddy, was a singer in her own right.

Despite his many links to the entertainment industry, Jennings’ life has been anything but a handout. Though his mother spent time as a backup singer for Waylon, she was determined to make it on her own, took multiple jobs, and kept her musical journey separate from the colossal legacy that comes along with the name “Jennings.”

“My mother decided that she didn’t really want to live off Waylon’s name,” Jennings once told American Songwriter. “She also had a thing for ‘bad boys’ and always dated guys who were a bit rough around the edges—my father and a series of guys after that being examples. So, I went through a lot throughout my upbringing—especially after my father was killed when I was 10.”

The death of his father pushed him into a life of crime. His run-ins with the law ultimately landed him in prison from 2011 to 2016. Since serving his time, Jennings has started on his own musical journey—one that infuses his own hip-hop tastes and his family’s classic country sensibilities.

Though he is on the up and up now, the effects of his prison sentence are still very much with him. “When I went to prison this last time, I lost everything,” Jennings continued. “I watched the mother of my children get addicted to drugs and eventually die from an overdose. I watched my kids go into state custody. Seeing all of the heartache and terrible things they were going through really gave me the motivation to come out and be the best father, man, and artist that I could be.”

All of that hardship and determination to do better is found within the 13 tracks on Monte Carlo. The title track opens with Jennings recounting the hard-won lessons he has learned on the streets in the absence of his father—which is largely the onus behind his life’s trajectory as a whole.

Elsewhere on ‘BURY MYSELF” Jennings reckons with the people he has lost in his life. On “Tears of Joy” he remembers the mother of his children who passed from a fentanyl overdose. Save a few upbeat numbers, most of Monte Carlo is a harrowing account of hardship and the long-haul journey to overcome it.

Jennings has detailed to American Songwriter the inspiration behind this album in its entirety. Check out Jennings’ track-by-track of Monte Carlo in his own words, below.

1. “Monte Carlo”

“’Monte Carlo,’ the title track, came from a conversation with a friend about how I hung on to everything my dad said before he died, and wondering if he would’ve said the same thing. Going through life and now that I’m older than he was when he was killed (he was 30), I look back at all that I learned from the streets since I didn’t have a dad. I wanted to tell my sons with this song what I’ve learned so they don’t have to fall for the same irrational beliefs I had to learn for myself.”

2. “Savior”

“This song is by far one of my favorites. It came from wanting to talk about how, if you ask 100 people about me, 90 of them will say I’m great and a good man but there will be a handful that have a different perspective. I’ve done my best to be a great man but everyone falls short sometimes, and everyone can relate to that.”


“I wrote this song at the funeral for the father of my step kids who died from a fentanyl overdose. After losing so many loved ones to drugs and violence, I let out all the emotions from constantly going through the loss with this song. It’s aggressive, but it’s honest. ”

4. “That’ll Be the Day” 

“This song is one of the most vulnerable songs on the album. It talks about the day I can relax and breathe. With everything I’ve been through, always having to swallow pain and keep moving forward, it talks about the day when the chaos calms and I can feel the breeze.”

5. “Not Hard to Find (ft. JD Huggins)”

“JD and I have both experienced a lot of loss in our lives. JD lost his son 3 years ago, and on the day we wrote this I had just found out the truth behind my dad’s murder. This was a letter to our loved ones hoping that when we get to heaven that they’re not hard to find.”

6. “Drinking Alone”

“’Drinking Alone’ is about a time when I was going through a breakup because of my drinking, and struggling with the question of, ‘Do I change and quit drinking or drink my sorrows away.’”

7. “Fell Outta Love (ft. Caitlynne Curtis)”

“This song is about getting caught up in old ways or vicious cycles, loving the lifestyle but having to fall out of love with drinking and toxic thinking and relationships in order to move forward.”

8. “Friday”

“’Friday’ is the summer song of this album. It’s about overcoming everything and working hard to get where you want to be so that every day feels like a Friday.” 

9. “Alligator Boots (ft. Yelawolf)”

“Yelawolf and I have such a great time in the studio together, and Alligator Boots is one of those things that came from me and him just having a fire track and doing what we love. My verses go out to all the people who have doubted me or counted me out over the years.” 

10. “Hard to Hate (ft. Jelly Roll)”

“Jelly and I have been best friends for 20 years, so we have been through a lot together. We’ve both changed so much as we’ve grown up, but there are always some things that will never change, including our friendship. We wanted to write a song about the things that we love and that we will always hold near and dear.”

11. “Forever” 

“’Forever’ is a love song to my wife about all the storms we have weathered and how our love is what brought us through it.”

12. “Something to Believe In”

“Everyone needs something to hold onto that gives you hope, whether it’s loved ones, your kids, your country, or God. This song is about the things we keep close to keep us going.”

13. “Tears of Joy (ft. Lorrie Morgan)”

“I cried like a baby trying to write this and record ‘Tears of Joy.’ This song is about the mother of my kids who died from a fentanyl overdose. Lorrie Morgan is a great friend and an artist I’ve always loved, so to hear her hauntingly beautiful voice sing this song was exactly what it needed to make it what it is and meant so much to me.”

Photo by Sebastian Marbury

Leave a Reply

Toby Keith Releases EP ‘America’ in Honor of  Memorial Day