The Complete Transformation Of Jelly Roll's Only Daughter, Bailee Ann

Jelly Roll has made no secret of his troubled past (which included dozens of arrests), and neither has his wife. Indeed, Bunnie Xo's life has also been full of tragedy and hardship, from being abandoned by her mother on a doorstep shortly after being born to surviving abusive partners. However, despite all their tribulations, both Jelly Roll and Bunnie Xo have ended up stronger than ever, building successful careers and a loving family life. Unfortunately, that didn't happen in time to spare Jelly Roll's teenage daughter, Bailee Ann, from experiencing her share of heartbreak, much of which occurred when she was still a young child. However, just like her dad and stepmom, she's risen above the challenges and is now forging her own path to a successful future.

Here's your look inside the complete transformation of Bailee Ann, from a baby who saved her dad's life – "Words can't describe how much of an impact my daughter has had in my life," the country star enthused on Facebook back in 2020 – to a tween who struggled with substance abuse to a sassy teen with her sights set on the White House.

Jelly Roll was just 14 the first time he was arrested, and he would spend the next decade in and out of prison, getting locked up a stunning 40 times. One of his most serious offenses came at 16 when he was arrested for armed robbery, charged as an adult, and faced 20 years in prison. In the end, he was out after 18 months, but even that harrowing ordeal didn't scare him off a life of crime. It wasn't until May 22, 2008, when a then-23-year-old Jelly Roll was in jail on drug dealing charges, that he would vow to turn things around. That decision came the moment a security guard informed him he'd just become a father.

Jelly Roll first met Felicia A. Beckwith through a mutual friend, and they had a short-lived fling before he was incarcerated again. The aspiring singer knew Beckwith was pregnant, but it wasn't until he learned of Bailee Ann DeFord's birth that everything changed. "My daughter saved my life, and she doesn't even know it," Jelly Roll admitted in his 2023 documentary, "Jelly Roll: Save Me," per Hollywood Life. He immediately signed up for a transfer to the education unit, got it, and passed his GED on the first try. "It was like a Damascus Road experience in the Bible," he later told Joe Rogan. "I didn't know what I was gonna do, but I knew that I was dead set on not selling drugs ever again." Indeed, after his release at age 25, he never broke the law again.

When Bailee Ann DeFord was born in May 2008, her father was in prison and her mother, Felicia Beckwith, was already dating someone else. As Bailee Ann told Bunnie Xo's "Dumb Blonde" podcast in 2024, the three of them lived with her maternal grandparents and "things were fine for the first couple of years." Once Jelly Roll was released from jail, Bailee was already two years old, but Beckwith didn't want him around their daughter. "Bailee's mother made it hard on me at first," Jelly Roll admitted in his 2023 documentary, "Jelly Roll: Save Me," per Hollywood Life. "She made me go to court to even see her." However, given the fact that he was constantly on the road and struggling with alcohol abuse, he was the first to admit, "I was a very less-than-present father."

It wasn't until 2016, when Bailee Ann was in kindergarten, that her home life began taking a dark turn. That was when Beckwith was diagnosed with fibromyalgia and prescribed painkillers. Slowly, she developed an addiction to the medication, which ultimately turned into a heroin addiction and thrust a young Bailee Ann into a self-described nightmare. "God, it was terrible," she told Bunnie [19:50] on her podcast. Similarly, while speaking about her upbringing in her father's documentary, she shared, "I had an extra, interesting, traumatic childhood."

Of all the sad details about Bailee Ann's life, one of the most heartbreaking is how much she went through when she was only a preschooler. Just as Felicia Beckwith had begun to struggle with substance abuse, so had her live-in boyfriend, and soon, a six-year-old Bailee Ann found herself living in a home where she had to fend for herself. Opening up about that harrowing time in her young life, Bailee Ann told Bunnie Xo's "Dumb Blonde" podcast in 2024, "The house was horrendous, like, nightmares." She was only in the first grade, but her mother had unfortunately become incapable of taking her to school, keeping the house in order, and raising her daughter.

Indeed, Bunnie recalled the first time she and Jelly Roll visited a then-7-year-old Bailee Ann at home and told listeners she was shocked by the squalid conditions. "The neglect in the house was just horrific," she revealed, noting how her future daughter didn't even have a bed. "My first memory of Bailee is her cooking dinner for her little two cousins," Bunnie continued. "It broke my heart." Despite being a child herself, Bailee Ann had been tasked with raising her aunt's two children when no one else would. In addition to feeding and taking care of them, she even resolved to sleep on the floor, so that one cousin could sleep on the couch and the other in a chair.

Despite Jelly Roll and Bunnie Xo's worries about Bailee Ann's tumultuous home life, she remained in that environment for several more years. Eventually, things got so bad that the electricity and water would regularly be shut off, and when her dad gave her mother money to pay those bills, the cash would go towards drugs instead. Even so, Bailee Ann revealed on Bunnie Xo's "Dumb Blonde" podcast that she saw Jelly Roll as the bad guy due to all the negative things her mom said about him. "I hated my father for the first, like, nine years of my life," she confessed.

Even so, Jelly Roll and Bunnie (who married in 2016) were determined to get her out of there. They filed for custody and, in 2016, the court ruled in their favor – all thanks to Bunnie. "I would have never got custody of my daughter without her," Jelly Roll told Billboard in 2023. "I wouldn't have had the stability or the money." Indeed, as he shared on the "Bussin' With the Boys" podcast in 2023, he was living in a van and didn't even have enough money to hire a lawyer. "Bunnie bankrolled the whole s***," he recalled, sharing how, despite the whirlwind start to their romance, "She said, 'No matter what happens with us, I'm gonna help you get this little girl.'" Looking back at that life-changing moment, Bailee Ann praised the woman she now considers to be her mom on Instagram, writing, "She built my world back up when it was broken in pieces and for that I am eternally grateful."

Jelly Roll isn't the only member of his family with a musical gene. In fact, Bailee Ann has been writing songs since she was 9 years old. Fans got their first glimpse of just how talented she was on 2019's "Sunshine After the Rain," followed by 2020's "Tears Could Talk." However, as the proud papa revealed on Facebook, Bailee Ann didn't just sing on the tracks. "My daughter wrote this verse all by herself," he enthused. As he later revealed on tour, per American Songwriter, "Bailee came to me and said that she wanted to do a song, and she told me she wanted to use writing as a means of therapy." Indeed, her lyrics were deeply personal, touching on her childhood and her mother's addiction. "I used to be Momma's little baby, but now I look at her like she's the villain," Bailee Ann rapped candidly.

In addition to finding catharsis in music, it strengthened her bond with Dad. Recalling their first-ever live performance together in Dallas, Texas, in 2019, a then-11-year-old Bailee gushed on Instagram, "The look of proudness in your eyes made me feel like I had just really improved." As of 2025, she was still pursuing music, even posting a clip of herself to TikTok, playing guitar and singing an original called "Fat in High School." "I literally just wrote this and idk if i like the end yet but enjoy," she mused, eliciting a long slew of compliments.

Jelly Roll and Bunnie Xo gained full custody of Bailee Ann in 2016, and her mother was absent for the next several years. However, as Bailee Ann told Bunnie Xo's "Dumb Blonde" podcast, Felicia Beckwith came back into her life in the sixth grade, right around the time she turned 12. Beckwith was in a sober living facility and, throughout 2021, they tried to mend their relationship. Things appeared to be going fine at first, but in 2022, that changed when a 14-year-old Bailee Ann decided to spend the summer with her mother. That choice put the teen in the midst of a toxic environment that soon saw her developing her own addiction.

"We start drinking together and I'm like, 'Okay, you're just a cool mom,'" Bailee Ann told Bunnie. Beckwith also gave her daughter marijuana and other recreational drugs. As Bailee Ann recalled, she didn't know her mother had relapsed until they visited her dealer on the Fourth of July and Beckwith asked if she wanted to get high with her. She initially refused, but told Bunnie, "I ended up doing it because she's, like I said, manipulative." Over the next eight months, she wasn't sober for a single day, either drinking, smoking weed, or snorting Valium or Xanax. Fortunately, she decided to get clean and cut off all contact with Beckwith, so she could make the most of her freshman year of high school.

Bailee Ann may have lost contact with her mother after deciding to get sober in 2022, but Felicia Beckwith's struggle with addiction has continued to impact her daughter's life. In 2023, Jelly Roll shared in his documentary, titled "Jelly Roll: Save Me," that Beckwith had once again gotten sober, but even so, he noted that it didn't wipe away his daughter's pain. "We're proud of [Beckwith], but it was really rough on Bailee," the singer shared, per Hollywood Life. For her part, Bailee Ann told viewers she had learned to move on, saying, "I've worked through my childhood." However, her dad wasn't buying it. In 2024, Jelly Roll spoke to Congress about the importance of anti-fentanyl legislation and shared personal insight into the impact addiction has on families, especially young children. "Every single day, I have to wonder if me and my wife, if today will be the day that I have to tell my daughter that her mother became a part of the national statistic," he said, per ABC News.

Offering additional insight into Bailee Ann's reality on a 2025 episode of "The Pivot" podcast, the singer shared, "My child's mother has struggled with drug addiction since my daughter's been born pretty much." Fighting back tears, he then revealed that a now 36-year-old Beckwith had once again been arrested and charged with several drug violations. "It's truly affected her life," he said of Bailee Ann, fighting back tears. "It broke my daughter's heart."

Jelly Roll has long been known to channel his fame for good, regularly harnessing his celebrity to help those in need. Like in when he used his 2023 tour to raise $590,000 for at-risk youth, when he donated Thanksgiving meals to inmates, or when he teamed up with Walmart to help orchestrate "the biggest toy drive in Nashville history." Fans were quick to praise the holiday initiative, which inspired so many donations that Jelly Roll was actually able to fill an entire semi-truck with the toys received.

As it turns out, though, it wasn't really his idea – it was Bailee Ann's. "It was kinda my daughter's dream, to be honest," the singer revealed while attending the CMA Awards, per Taste of Country. As he explained, he was simply taking his daughter's own philanthropic efforts and replicating them on a bigger scale. "She started doing it at a real small local level with her aunt that owns a bar in Whitehouse, Tennessee, for the last five years," he said of Bailee Ann's initiative, which is named Buddy's Toy Drive after his late father.

Bailee Ann went through her own struggle with addiction when she was just 14 years old, but luckily, she made the choice to get sober and focus on her studies instead. Even so, Jelly Roll wasn't taking her sobriety for granted, instead choosing to have some very real conversations with his daughter in the hopes of inspiring her to stay on the right path.

Speaking with People in 2024, the singer noted he's not afraid of using tough love to keep a 16-year-old Bailee Ann from making excuses to not reach for the stars. "When I'm hard on her about stuff or a little pushy, she knows it's from love," he told the mag. Sharing details of one particular pep talk he had recently had with his daughter, Jelly Roll explained that it's all about getting Bailee Ann to never follow in his footsteps. "I don't judge you based on what you do, I judge you based on what I know you're capable of," Jelly Roll told the teen. "'You're so much smarter than I was at 16; you're so much better; so much more emotionally intelligent."

It seems Jelly Roll's pep talks are hitting home since Bailee Ann is serious about her studies and her future. Back in 2022, when she first started high school, the singer took a moment to boast about her achievements on Facebook, writing that she was in "all honor and advanced placement classes." Encouraging her to enjoy her experience, he mused, "Don't take anything too serious except the curriculum."

That advice didn't fall flat as a 16-year-old Bailee Ann revealed during a 2024 episode of Bunnie Xo's "Dumb Blonde" podcast that she had lofty academic goals. "I wanna go to Columbia for law," she said of her post-high school plans. "As for music, I don't have any plans to do it right now – I don't know if I ever [will]." Bailee Ann revealed that she was initially interested in studying medicine, but ultimately changed her mind. "I hate western medicine," she explained. "I hate the way that we handle health and health insurance and everything." Instead, she'd like to focus on criminal defence and possibly specialize in cases involving narcotics. "It's very complex, morally and legally," she mused.

Whatever career path she ends up following, though, she's planning to crush it. "Whatever field I get into, I'm ready to turn it upside down," Bailee Ann proclaimed, adding she wouldn't mind being a congresswoman or judge. Setting her sights even higher, she quipped, "Jelly Roll's daughter – president."

Valentine's Day 2025 proved to be a big milestone for a 16-year-old Bailee Ann as she went on her first real date. Mom Bunnie Xo made sure to be on-hand as she got ready to go out for dinner and documented the moment on TikTok, joking, "Can she stop growing?" In the clip, which Bunnie cheekily captioned with "I'm not OK," Bailee Ann shows off her casual outfit made up of baggy jeans and a cropped top and jokingly fends off a slew of questions about her suitor. Just before heading out, Bunnie hands her emergency cash and imparts some important words of wisdom, advising, "If you pay for dinner, that's the last time you're going on a date with that dude."

That obviously wasn't the case because the following month, Bunnie confirmed Bailee Ann was officially dating a boy named Gabe. Taking to TikTok, she introduced fans to "Gabe the Babe," as she dubbed him, and filmed them preparing a secret promposal for Bailee Ann with help from Gabe's mom. As she showed off in a later video, Bailee Ann said yes, although she jokingly told her beau, "This is the most unnecessary thing you've ever done," as she arrived home to find red roses on the floor and Gabe waiting for her with a bouquet and a sign asking her to be his date to prom.