Jelly Roll Reveals the Story Behind His Powerful Tattoo of ‘Redemption’ and ‘Second Chances’

Wherever Jelly Roll is journeying, it’s with flair.

The 40-year-old artist has recently unveiled his second partnership with HEYDUDE and states that regardless of the event, you can always spot him adorned in the brand. “My team can confirm this firsthand: We go from the hotel to the airplane to the performance to the gathering to rehearsal, which is something to cherish, but you are even more thankful when you can remain comfortable as much as possible,” Jelly Roll shares with PEOPLE. 

The musician, who notes he’s donned HEYDUDES “on the red carpet, in performances, rehearsals for SNL, everywhere,” confesses that this moment makes him feel exceptionally fortunate. “From the people I represent and the individuals I advocate for in America, also within country music, to being among the first country artists to have my own footwear… I don’t know man, it’s just awesome and it could have happened with anyone,” he reveals. 

Jelly Roll adds, “I’m a dude nonetheless, and it worked out seamlessly… They’re budget-friendly, yet stylish. I come from a middle-class, lower-income background and you can wear these with dignity.”

It’s not only his footwear that symbolizes Jelly Roll. The “Lonely Road” artist is also recognized for his tattoos, each narrating a tale. “My broken chains — want to hear the story behind these? This is interesting,” he states. “The broken chains are inked on my arm. One, it symbolizes breaking free from life’s chains — anything that confines us, any bondage we possess, any addiction, anything we believe God can’t assist us with. We can shatter those chains.”

The inspiration for the chains manifested through music. “It originated because Taylor Phillips, Jackson Dean, and I penned a song on the bus titled ‘I Can’t Break These Chains,’” he shares. “We cherished the song so much that we got the tattoo of the breaking chains that very day. And we still haven’t released that song! We should definitely put that track out.”

It only made sense to embed those chains into the sneaker design. “I love that this emblem is featured on the shoes. It’s Jelly Roll represented all over the footwear — redemption, second chances, self-confidence, faith, family. I stand firmly on all I believe in when I wear these shoes.”

Jelly Roll is celebrated for embracing second chances, frequently reflecting on his history as a convicted drug dealer and addict. “I believe second chances must be earned,” he states. “I think at times you can earn them through opportunity — there are prospects for earning — but I maintain that second chances are something that must be earned.”

With his renewed chance, Jelly Roll has afforded himself fresh opportunities, ignited change, and can scarcely believe how his life has transformed. “There are countless experiences that in real time you can’t fully grasp they are occurring because how can you believe you’re at this performance or conversing with this individual,” he conveys to PEOPLE. 

He remarks, “But if you’re asking me what I take the most pride in, it’s returning to visit the youth at the detention center and having the chance to engage with various facilities across the nation and now internationally when I’m on tour and listening to the narratives of those who feel they may not always be represented. Being allowed to speak on a genuine level with someone about how they are just one good decision away from transforming their life and being back on course is something I don’t take lightly that I get to do.”

Jelly Roll is committed to leveraging his journey to motivate and uplift others, never taking any moment for granted. “Demonstrating that second chances are attainable? There is nothing I cherish more,” he states. “And I desire to keep being an example of that.”