Growing up, this rapper was frequently in and out of jail and lacked the home stability needed to develop a healthy relationship with food. He struggled with his weight for years, but by 2025, he had made some significant progress.

This singer came from poverty to achieve his current success, and although he faced widespread hardship, his most persistent challenge since childhood was his weight. Here’s the story of how he eventually lost more than 100 pounds—and what he looks like now.

Growing up Poor and In and Out of Jail

This star was the youngest of four children in Antioch, with the other three being his older half-siblings. He was the only child from his parents’ union, though it was his father’s fifth or sixth marriage.

The

singer grew up

in a “very rural” neighborhood southeast of Nashville. He recalled the area’s racial diversity and described the residents as mostly middle or lower-class. Reflecting on his upbringing, he

said

, “I don’t think I knew anybody with a real job,” and admitted he also didn’t know any barbers.

Despite his poor background, this vocalist recalled that he never truly went without, thanks to his father, a hustler who worked as a meat salesman and bookie. His father often made bets to bring in money. The star remembered feeling like their home was a big middle-class house.

However, as an adult, he

realized

the house was quite small—more like the size of a “garage.” Meanwhile, his mother struggled with mental health issues and substance abuse, which began with pills.

He recalled how reclusive his mother was, rarely leaving her bedroom. On the rare occasions she did, the singer

reflected

, “I’d watch the temperature change.” She would come downstairs, sit at the table, and light a cigarette.

He

remembered

how his mother would “hold court” while neighbors flooded into their home. She would tell wild stories and play records, creating what he

described

as a “cool atmosphere” in the house.

These gatherings happened only twice a year, but sadly, when he was just 13, his parents divorced. He was left feeling responsible for his mother. In 2019, before his father’s death, the star shared his thoughts with him.

He wondered if life would’ve turned out differently—perhaps he would have gone to Vanderbilt University—had he moved in with his father after the divorce. However, he had felt compelled to take care of his mother, and that sense of responsibility eventually led him into crime.

The singer

said

, “When he left, I was like, ‘Somebody’s got to do what he was doing, at least trying to figure out some money.'” He also shared how unstable his mother was. The star said he had never seen his mother out of her nightgown until he was tried as an adult at age 17.

His mother showed up at court wearing a T-shirt, sweatpants, and house slippers. The rapper joked that he knew he was getting off since she’d cared enough to come. He also shared how he made money before teenagehood. As a preteen, he earned an allowance by waking up early on Sundays to gather betting slips from the day before.

He

shared

, “ESPN didn’t run what happened between Alcorn State and Northwestern. If you wanted to know what happened between Bowling Green and whoever, I was the guy.” He was actually a teenager when he first brushed against his future success in rap.

Working on Finding Fame

His journey out of poverty took decades. He wrote his first rap at age nine or ten. By eighth grade, he was handing out his mixtapes in the high school parking lot. There was a place in his hometown where they could cut demos for $30 an hour. The singer

said

, “We had a dude who had a rolling keyboard and he’d make beats.”

At 15, while out on his first-weekend pass from a juvenile facility, a friend invited him to a car show in nearby Lebanon, where his cousin, Nashville rapper Haystak, was performing.

The singer

recalled

, “For the first time in my life, I’m in the room with somebody with a big chain, a Rolex, he’s dressed cool as [expletive], everybody’s saying ‘What’s up’ to him, girls are flashing him on cars. It’s wild!”

Recognizing

him as “the kid who’s locked up,” Haystak asked him to rap. He seized the opportunity and

received

praise, along with the advice to “stay out of trouble” because “you’ve got something.”

Although he failed to avoid jail, he continued to build his rapping career, even becoming close collaborators with Haystak. Still, he

admitted

that singles like “Welcome to the Trap House” and “Pop Another Pill” were “misleading.”

However,

those tracks allowed fans

to understand “the depths of who I was,” with more introspective songs buried deeper in his albums. As he started selling a few hundred tickets to shows around the South, he noticed a stronger audience connection to his more contemplative music.

This trend shifted his writing style, with only a few of the dozens of tracks he recorded for each album exceeding 65 beats per minute. He once

said

, “My soul is to write ballads—that’s what pours out of me, dude.”

His current creative process combines emotional authenticity with technical dissection. He

explained

, “It’s still precious to me. I kind of enjoy feeling that way; I’m still glad I get real palm-sweaty before interviews, get real nervous before shows. I love that. I’m still here for the right reasons.”

Now, his goal is to reach children facing circumstances as difficult as his once were. By 2024, the juvenile facility where he spent his 15th to 17th birthdays had started offering writing workshops to residents.

Each cell block hosts a workshop to reduce the risk of violence. He aims to write a hit song with one of the incarcerated youths. The star

believes

that if he had seen what success looked like or had access to a studio while in jail, “I’d be light-years ahead of where I am.”

During one visit, he and a child in the facility went through a “Who’s on First?” routine. The kid

asked

him, “Why are you here?” to which the rapper simply replied, “‘Cause I was here.”

Showing how much he loves and honors his late father despite being a

famous rapper

, Jelly Roll uploaded a throwback picture in March 2022 featuring his two older brothers—whom he’s still close to—and his paternal grandmother.

Roll mourned his father, describing him as an incredible man of few words. “I’ve carried the lessons he taught me through life everyday [sic],” the rapper

said

. He

added

, “One of his last conversations with me was how proud he was of me . [sic]”

The rapper expressed how much he wished his father were still around to witness his continued success. “He taught me how to live and he showed me how to die. He didn’t cry one time laying on his death bed just smiled and told stories. Miss this man every day of my life.😢[sic]” he

concluded

.

His father’s death wasn’t the only hardship Roll faced. Throughout his life, he endured bullying because of his weight.

Roll’s Weight Loss Struggles

In 2017, Roll posted a throwback photo of himself on Facebook,

noting

that he was “180 lbs heavier than I am right now” in the image. He

wrote

, “I’m just getting started on this health journey. I’m about to dedicate the winter to really getting my heart right. I FEEL A SPRING TOUR COMING!”

The following year, he uploaded a new photo, flashing a lewd hand gesture and smiling. Reflecting on the past, he recalled hitting a devastating low point in 2015 when he discovered he weighed over 500 pounds—so much that a regular scale couldn’t register him.

The moment was not just humiliating—it was a harsh wake-up call made worse by destructive coping habits: overeating, drinking, and substance abuse. It wasn’t until late 2016 that he began a slow, determined journey to reclaim his health and ultimately lost around 200 pounds.

However, the unhealthy lifestyle of touring—late nights, junk food, and constant alcohol—led him to regain 60 pounds in early 2018. This setback reignited his ongoing battle with obesity and addiction. Roll declared that day a fresh start and recommitted himself to change.

He also launched a YouTube series

called

“Fatman Fridays” to document weekly weigh-ins and hold himself accountable. He didn’t go it alone—he brought in a fitness mentor and friends for support.

Roll thanked his community for their encouragement and expressed his desire to live life fully—whether that meant skydiving or riding roller coasters. He invited fans to help, asking for tips on meal prep and gym contacts, stressing that his journey was far from over.

In 2021, he shared another Instagram photo, opening up about his lifelong battle with depression. He revealed how this mental health struggle had shaped both his personal life and his creative work.

Roll shared that he was

diagnosed with manic depression

at a young age. He described experiencing intense highs—filled with creativity and confidence—followed by long, silent lows of emotional withdrawal.

These cycles affected everything: his music output, online activity, and health. They led to erratic posting, weight swings, and recurring addictive behaviors. He admitted that behind his outward joy was deep emotional pain, often hidden behind humor.

The singer explained that fear of judgment had kept him silent for years. But now, breaking that silence was part of his healing—and his promise to stay accountable. He committed to continuing his music and sharing his journey, regardless of his mental state.

The rapper hoped his openness would foster empathy and inspire others to speak up or support someone in need. In his post, Roll extended heartfelt thanks to his followers and expressed hope for continued healing, connection, and creative progress.

In May 2022, the star explained on “The Bobby Bones Show” how he got his nickname—saying it’s because he looked the part. He shared that his mother gave him the name,

saying

, “I’ve been fat my whole life.”

Roll joked that he spent 30 years growing into the nickname. However, in a later interview that year, he revealed his goals for the upcoming months. “I’m going to spend the first couple months of the year just focusing on family and health,” he

said

.

The singer

added

, “I lost some weight this year,” but hoped that 2023 would be the year he truly made progress. He

continued

, “I don’t leave for a big tour until about the middle of the year. So I plan on taking the first half of the year to tighten the album up and get some work in.”

By April 2024, his wife, Bunnie XO, spoke on her “Dumb Blonde” podcast, revealing why Roll had stepped away from social media. She said he was tired of being bullied about his weight, which deeply hurt him.

XO admitted that the bullying made her want to cry,

describing

her husband as the “sweetest angel baby.” She said that although Roll didn’t show it, the comments hurt. She urged listeners to be kinder, reminding them that others might be struggling mentally.

In November, her husband proudly revealed the results of a year’s hard work: he had lost 110 pounds. The “Winning Streak” singer

said

, “The battle was with the food addiction, changing the way I’ve looked at food for the last 39 years.”

The star

added

, “I’ve never had a healthy relationship with food, so that was the hard part. But once you get into that discipline and commitment, it’s like an avalanche. Once that little snowball started rolling, it was on its way.”

Roll estimated that he’d dropped 60 to 70 pounds during his Beautifully Broken tour, which ran through August. To stay active, he played basketball with his crew and prioritized healthier routines while touring.

Roll

said

, “It’s cool because there was once a time in life that the culture I built on tour was the opposite. It revolved around alcohol and [substance abuse].” He

continued

, “And now our tour culture is around good eating and around exercising and doing emotional check-ins with our crew every day.”

The musician attributed his unhealthy relationship with food to his upbringing. “Nobody in my house ever had [a healthy relationship with food], so that was the hard part, really fighting that demon at first and getting into that discipline and that commitment,” he

admitted

.

That same year, in December, during an interview with his wife on her podcast, Roll

reflected

on his weight: “I became a success in spite of it.” He revealed that he once weighed 550 pounds. His wife commented that his success worked despite his size because he had the mentality of a skinny man.

XO elaborated, “You are a skinny man trapped in a big guy’s body.” By April 2025, Roll shared another update on his health journey. During a live appearance, sports analyst Pat McAfee joined him onstage and

remarked

, “It looks like you lost a person.”

Celebrating the milestone, McAfee invited Roll to share more. The rapper proudly

declared

, “I started at 540 pounds and I was 357 pounds this morning, baby!” He

added

, “I’m gonna lose another 100 pounds and go skydiving with my wife in Sweden!”

Beyond his weight loss, becoming a father played a pivotal role in helping Roll set his life straight.

Jelly Roll, the Family Man

While in jail in his twenties, Roll learned that the woman he had been seeing was pregnant. He

admitted

, “I was just irritated by it. Like, ‘I’ve really [expletive] up now.'” But when his daughter Bailee was born, her arrival became the turning point that inspired him to change.

After being transferred from the violent offenders’ unit to the education unit, he started working toward his GED. “I spent less than 60 to 70 days in high school. I thought I was a real dumbass. I thought I was learning disabled,” he

said

.

Roll finally met his daughter when she was two years old. They celebrated his release by grilling burgers and hot dogs together. Today, Bailee lives with him and his wife, and he also has a son, Noah—nicknamed “Buddy”—from another relationship, whom he sees often.

The rapper credited his wife, XO, for helping bring stability to his life. He

called

her “a beacon of change in my life” and expressed deep gratitude, saying, how she bravely took in a child that was soon to be born and another one they were going to have full custody over soon.

Roll

added

, “I would have never got custody of my daughter without her. I wouldn’t have had the stability or the money.” In another interview, he

said

this about his wife, “My world shrunk when I focused on one woman.”

The couple first met at one of his shows in 2015 and eloped in Las Vegas the following year. After leaving jail, Roll committed to pursuing music as a career—releasing albums independently, posting on YouTube, and taking any gig he could find.

From 2010 to 2015, he lived in an old van and traveled wherever there was work. He

recalled

, “I’d go to Columbus [Ohio] and do $50 features; I’d sell rap verses for 50 bucks,” adding, “I was so petrified of sitting idle because I was afraid I would resort back to what I felt like I knew.”

Roll now credits his family as the foundation that keeps him grounded while navigating fame. “I prioritize family, and that’s what anchors me down,” he

said

. He

added

, “Everything that I believe going right for me is in the fact that I’m pretty grounded in my family. [sic]”

Jelly Roll

‘s story is one of perseverance, transformation, and love. From struggling in a rural town to becoming a symbol of redemption, his journey continues to inspire many.