The Troubadour of Troubled Souls

We talked to Struggle Jennings

© Struggle Jennings

Rapper, father, outlaw – whoever is trying to pinpoint Struggle Jennings is facing a difficult task. But those who know Mr. Jennings better will realize that his name actually is a perfect description of where he comes from – and where he is heading towards.

“Don’t You Think This Outlaw Bit’s Done Got Out Of Hand”, asked country singer Waylon Jennings in his famous song in 1978. And “Don’t you think this outlaw shit has gotten out of hand?”, composed Struggle Jennings, over 30 years later. The outlaw blood has been running strong in the Jennings family. As the grandson of country musician Jessi Colter, step-grandson of Waylon Jennings and nephew of singer and producer Shooter Jennings, 41 year old Struggle has a famous family background to show off with. Yet, he has proven to be an artist very much of his own, with a rap style that’s very distinct from everything his ancestors have ever done.

“I feel incredible right now”, says Struggle, and smiles widely into the camera. Which doesn’t surprise, as his song “God We Need You Now”, with Caitlynne Curtis singing the chorus, has recently topped the hip hop charts of Itunes and the Billboard Independent Charts as well. “It meant so much to me, especially with all the issues the song is dealing with and that the world faces right now. The song is a plead to find unity, peace and God. But it is also so important for me because it is an entirely independent work”, says Struggle. He has recently founded his own independent record label called Angels & Outlaws, after having previously been signed to rap colleague Yelawolf’s Slumerican. “I can see the song means something to the people, they can embrace it, even though I don’t have huge followings or a big label behind it.” Struggle is sitting in his car, busy on his way to loads of other appointments he has today. He has just finished his US tour with several concerts on the continent. “The tour was amazing. Our tour bus got hit by a drunk driver and we had to cancel a couple of shows due to the strict regulations. But I could meet so many fans, talk about life.” Fans, this is one thing Struggle doesn’t become tired to mention, are one important part of what keeps him moving. “I felt like I was really out there making a difference. People have told me my music helps them through hard times, getting sober, being better fathers and mothers. Watching so many people heading towards my music is very amazing, because I have never been the mainstream kind of person.”

“I felt like I was really out there making a difference.”

Born by the name William Harness, Struggle grew up in Nashville Tennessee and started releasing music in 2013, first appearing on Yelawolf’s mixtape “Wyte Dawg”, then with his first album “I am Struggle”. In the following years he did several EPs, among them “Return of the Outlaw” (2016), “Spiritual Warfare” (2018) together with his mother, “Sunny Days” (2019) together with his daughter and music newcomer Brianna Harness. In the same year he also released his second studio album called “The Widow’s Son”, followed by “Angels & Outlaws” at the end of that year. 2020 brought the EP “Legends” together with rapper Adam Calhoun, and this year was marked by major successes through the solo LP “Troubadour of Troubled Souls” and another collab with Calhoun. Over the past years, Struggle has also done several record collaboration series with his long-time friend and rapper Jelly Roll, called “Waylon & Willie”.

Music having always been part of his life, it has been as much for himself as for the people around him. “On the one hand, music is definitely for me. I can pour my heart out and that helps me. But I don’t want to forget others. I inspire them as they inspire me and I do everything with that in mind. I don’t want to glorify what I have overcome. Success is not monetary, but about peace and doing what you love.” With so many people looking up to him for hope in their lives, Struggle has especially been standing for one thing: The ability to change yourself and your life, and take your life into your own hands. Which, for once, is not as easy when you look at what lifestyle the rapper had been leading in the past. Being in jail for five years from 2011 to 2016, Struggle can tell perfectly well how street life and gangsta business can turn one’s life upside down. “I was in prison two times, shot twice, I went through about everything a man can go through, lost some of the closest people in my life, had drug addiction… I think there is nothing I haven’t seen”, tells us Struggle, and becomes quiet for a moment. But then he looks up and the twinkle is back in his eyes. “But here I am. I could share those stories all day long, but I have made it here. There is more to life, and there is always a way out.” This is the one thing Struggle is also trying to convey to the fans who look up to him. “Sometimes I feel like I was there to give testimony, to speak for the people who fought in the same trenches.” The trenches are deep, and not all have had enough fighting spirit and luck as Struggle to find out. As he tells us, he was in jail mostly for drug charges, accused of selling 200 kilos of cocaine, his federal charge was dealing oxycodone. “I was never caught with drugs, and some things were made up. But I was out there doing wrong. I got charged for some things I did not do, but I also did some things I wasn’t charged for”, says Struggle, and his honesty is remarkable.

“Sometimes I feel like I was there to give testimony, to speak for the people who fought in the same trenches.”

© Struggle Jennings

This gangsta lifestyle, though, has left his marks on him and the people around him. He has had to bury 40 close friends he lost to gang conflicts and drug abuse. “I lost a lot of friends to overdose. The mother of my children died last year, my stepkid´s father died this year. And it continues, it has never stopped”, says Struggle, who knows that his name is more than just playing with words. “But there has always been a silver lining. All this has inspired me to continue doing good, to work harder to show the people that they can overcome their lifestyle, poverty, drug addiction, anything.”

This is what Struggle, now clean, law-abiding, successful, has as his goal. “My entire music and my brand are about overcoming, about transgressions, perseverance. For me it is a determination to get my children a better life, to become a better person. My music is all about change. Regardless what you are, you can overcome it”, Struggle explains, and he means it. For him, it is constant growth. In the music video of the song “Good Die Young”, part of his latest album “Troubadour of Troubled Souls”, he can be seen burying his old self, and returning to his family and home. “I want to throw away all that keeps me from growing to be the man and father I want to be. There are still certain things I need to let go of.”

“My entire music and my brand are about overcoming, about transgressions, perseverance.”

When asked about where he takes his strength from in the face of all the losses he continues to face, he doesn’t hesitate a second to answer. “I find strength in my family and the fans who tell me my music helps them through life. My kids have been through a lot while I was gone, and I never want to put them in that situation again.” When Struggle came out of prison, he had to get back custody for his children, who where then living in foster care. One of the most touching songs, as many fans feel, is “Like Father, Like Son” – a song where Struggle raps about the apple not falling far from the tree, and him becoming the same criminal as his father. But now, with him striving to be the best father possible, this song has got an entirely different meaning. “I learned in prison that I got to be the man I want my sons and daughters to become. When they’re gonna chase the road I took, I want to make sure it is the right one.” In order to achieve that, he has shared a lot of his inner thoughts and experiences with the public trough music, and has talked about very private things in his songs. “Of course I feel vulnerable. But on the other hand, I think I have this responsibility. Some people think to be a tough guy you have to hide all your emotions and tears. But a tough guy does not have to remind you he is a tough guy. My weakest point is my strongest point.”

“I learned in prison that I got to be the man I want my sons and daughters to become.”

As it is not hard to read from “God We Need You Now”, faith has been very important for Struggle as well. “It has kept me alive my whole life. My grandmother and mother were very spiritual and raised me that way. And even on the craziest paths I felt I had protection because of them praying”, he reminisces. “I have been to situations I probably shouldn’t have made it out alive. So I always had a strong sense of God.”

While his story and lifestyle may have countless facets, so does his style of music. His mantra is to make the music just as the emotion is, without any strict adherence to the genre. Yet, country music has always been a big influence to Struggle’s hip hop. “I have love and appreciation for country, and I started blending genres as I love country instruments.” But that does not really make him a country rapper either. “I stand apart from most people in that genre because they rap about country stuff. I am a city kid and do different content.”

“A tough guy does not have to remind you he is a tough guy. My weakest point is my strongest point.”

With everyone knowing the name Jennings, it has not always been easy for him to step out of that shadow. “At first it was hard and I did not want any connection with that name. I just called myself Struggle.” He only started using the name Struggle Jennings during his time in jail because one media outlet called him that way. “I did not like it at first. But Shooter gave me his blessing and said, grandpa would love it. So it became part of my story.” As Struggle recalls, Waylon Jennings was a huge inspiration for him. When his dad was murdered as he was ten years old, the country icon kept him up and influenced him both as a man and as an artist.

Nowadays, it is not only the street anymore that moves him. Struggle may not be an explicitly political rapper, but he is becoming increasingly troubled about the current situation his country is facing. “2020 has caused a bigger than ever divide. The media and the government are stomping on the morals I was raised upon. They are infecting the mind frame of our children. I find that so disturbing.” Struggle is distressed by what the United States – and he does not want to hide his patriotism – are developing into. “I want to preserve the values I was taught: Always treat everybody with respect, don’t judge a man by its cover, judge a man by his character.” This is also why “God We Need You Now” came out, a song that criticizes the growing political divide, the loss of values and principles. “I just came to a point where enough is enough”, says Struggle.

Imprinted on his motorbike is the Second Amendment of the United States constitution, granting the right to bear arms to protect oneself. “I feel this is mandatory. It is about freedom – we don’t work for the government but the government for us. Anyone should be entitled to protect their families because I do know very bitterly how dangerous it can be out there”, explains Struggle. He is not too happy at all with the Biden administration, he is willing to explain, economically on the one side, but humanitarian on the other: He mentions the bombings in Syria, all the people left behind in Afghanistan by the US government. “America is supposed to be the state where people come to from anywhere in the world to chase the American Dream. To achieve something by hard work and determination.” For him, the American Dream of course bears a very personal connotation: “Five years ago I had nothing. Now I have a huge home where every one of my kids has got their own bedrooms, and a swimming pool.”

“America is supposed to be the state where people come to from anywhere in the world to chase the American Dream. To achieve something by hard work and determination.”

©Struggle Jennings

He does not want to leave it on personal level though. Part of his most recent album is the song “Cry for Help”, a strong plead for the safety of children against molesters and rapists. Struggle even sells t shirts saying “Kill all pedophiles”. “I got seven kids”, says Struggle, and for him that is everything. “One of my daughters got molested while I was in prison. The last year opened up my eyes on how often it really happens. With Donald Trump we had the most pedophile president in US history. Watching all this being exposed made me feel like I had to voice this”, says Struggle, and remembers how his dad told him to always protect women.

It is the paradox that really makes Struggle to the intriguing rapper he is today: Having been a true gangsta, not only talking about, but committing crimes, embracing the suffering of the underdog, and yet convinced to always stand up as a role model –  for being a good father, for overcoming a lifestyle in the trenches and for showing that man is able to change for the good. Just like his grandfather, founder of the outlaw movement, Struggle has been and is an outlaw. “An outlaw is not always someone running from law”, he says. “It is someone who is true to themselves, who does not conform to what other people want them to be, who blazes the trail and makes their own way. In that way, I have been an outlaw for a long time, and I still am.”

By Katharina Moser


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