Controversies Jelly Roll Has Been Wrapped Up In

Jelly Roll's been through a lot of ups and downs, and his lyrics certainly reflect that. In a 2024 interview with Billboard, he described his songs as "real music for real people with real problems," adding, "That struggle is something that a lot of my music touches on. It's something I am honest about with my own life and something that's for anyone who is going through that."

He knows real problems. Before his career took off, the acclaimed musician dealt with legal woes, substance misuse, and serious relationship issues. His life has calmed down in recent years, but that's not to say Jelly Roll's done stirring up controversies or raising eyebrows. For example, in 2013, Jelly Roll landed in hot water with Waffle House because he named his mixtape "Whiskey, Weed & Waffle House." "That's called trademark infringement," Jelly Roll explained on a radio show years later, per Whiskey Riff. "I didn't know this at the time. And they sent me a cease and desist letter and they froze my YouTube channel up and they threatened to sue me. It was kind of a big debacle." They reached a $10,000 settlement.

No matter the debacle, Jelly Roll seems to roll with the punches. From lawsuits to fan drama and beyond, the "Need a Favor" singer is no stranger to controversy.

Before he became a public figure, Jelly Roll racked up a long arrest record. His first visit to jail happened after he got nabbed for possessing cannabis and a pack of cigarettes while underage. He was supposed to take the citation to court, but his failure to do so landed him behind bars. He told The New York Times, "The police had to show up and haul me to jail. That was at 13. At 14 I think it was a schoolyard fight."

In his teen years and early 20s, Jelly Roll went to prison 40 times for a variety of charges. On a 2024 episode of "The Howard Stern Show," he spoke candidly about prison fights he'd been in and even how he got his first face tattoo. When he was 16 years old, Jelly Roll was given an aggravated robbery charge that had him facing up to 20 years in prison. He only served about a year of the sentence with a seven-year probation afterward. In 2009, after he'd been incarcerated for dealing drugs, he was released from prison for the last time. During his final time behind bars, he learned he'd become a father.

And though he has come a long way, Jelly Roll looks back on the time with a hint of resentment towards what he believes to be an unfair system. He told Billboard, "They were talking about giving me more time than I'd been alive. I hadn't hit my last growth spurt. I was charged as an adult years before I could buy a beer, lease an apartment, get a pack of cigarettes."

If you're a loyal "Dumb Blonde" podcast listener, then you know Jelly Roll and Bunnie XO not only have an open relationship, but don't worry about who might be sliding into each other's DMs. As Jelly Roll said on "Taste of Country Nights on Demand" in 2024, "We just don't live in that world of unnecessary jealousy." And yet, when Bunnie XO met one of her "hall passes," Chris "Motionless" Cerulli of the metal band Motionless In White, it sparked some drama among fans. In April 2024, she shared the moment she got to shake hands with Cerulli before a concert on TikTok. She also made a suggestive gesture while she watched him perform. Alongside the video, she wrote, "you could say we're in love now." 

Jelly Roll was all about his wife's cheeky TikTok, commenting "Bout time" along with two cry-laughing emojis. Despite Jelly Roll's endorsement, there were still some people who questioned their marriage and whether or not the post was disrespectful. As the controversy continued to bubble up, Bunnie XO shared a screengrab of her text conversation with her husband on Facebook. After Jelly Roll told her the post was "so funny," she replied, "I thought so too but ppl are offended ofc lmao." In the caption, she added, "So many ppl offended & upset about my 'hall pass' video. When my husband & I are just giggling over it." 

She continued, "Sorry y'all aren't comfortable in your own skin & too insecure to let your s/o joke around. I'd hate to live in a cage like that. Y'all forget my husband is my bestfriend & love of my life."

In Texas it might be common knowledge that you're not supposed to cuss at the family-friendly event that is the Houston Livestock Show and Rodeo, but that unofficial rule seemed to slip Jelly Roll's wife's mind. As Bunnie XO shared on TikTok, Jelly Roll invited her to the stage during his performance at the rodeo in March 2024. When he handed her the microphone and asked her to say something, she yelled, "Houston, what the f*** is up!" This was a big no-no, In the TikTok, Bunnie XO highlighted Jelly Roll immediately turning away as if to acknowledge the rodeo faux pas. It was, as she put it, "the look of despair."

In the aforementioned TikTok, Bunnie XO explained that she'd been put on the spot, as she had already told Jelly Roll that she did not want to go onstage during his performance. "No. I'm already weird and awkward as it is. I'm not good with a microphone or with crowds and I stick to a script that we have done for the past frickin' decade," she recalled telling him. 

The controversial NSFW moment generated some hubbub — namely, there was a lot of concern about whether or not Jelly Roll would be invited back to the rodeo. However, the rodeo's TikTok account assuaged any fears in the comment section of Bunnie XO's post. "Y'all are always welcome at RODEOHOUSTON," they wrote.  While the coarse language might've ruffled some feathers, Bunnie XO's certainly not the first to slip up. Maroon 5 singer Adam Levine who also had to publicly apologize for using an obscenity during a show at the rodeo, per the Houston Chronicle. 

Jelly Roll's appearance at the 2024 NBA All-Star Weekend in Indianapolis wasn't a total slam dunk. The musician was booked to play an event that weekend, but apparently he took the stage way later than fans expected. As Wide Open Country reported at the time, doors opened at 9:00 p.m., but Jelly Roll did not perform until closer to 11:30pm. 

Fans took to X, formerly known as Twitter, to complain about the long time between doors and show – and Jelly Roll wasn't having it. In a post on X, he said, "I just wanna clear up any misunderstanding about the Indiana show last night. I wasn't allowed to go on until 11:30. That's the way it was set up in the contract and told to only do an hour. I would never leave fans just waiting that late, it was completely out of my control."

But some fans had even more time-related complaints, with one fan claiming on X that Jelly Roll only played for 45 minutes. But Jelly Roll had his eye on the clock too. "I played for 57 mins — for sure — and was mad at myself for coming off those 3 mins early, sometimes when the crowds really good the show goes by quicker than normal — last night was a fun crowd," he replied. "So we kept the energy flowing."

Apparently the world is not big enough for two rolls of jelly. In what could be the precursor to a federal lawsuit, a Philadelphia-based wedding band called Jellyroll has filed a legal complaint against... Jelly Roll. According to the 2024 complaint, which was obtained by Billboard, the wedding band claims that the rap-country artist's name violates the group's trademark rights. The band's attorney alleges that Jellyroll is having a harder time booking clients because their SEO is not as strong as it once was, thanks to the incredibly popular solo musician with a very similar name. 

For what it's worth, Jelly Roll, whose real name is Jason DeFord, has had the nickname since he was a kid. In 2003, he used the name when he released the mixtape "The Plain Shmear Tape." Despite multiple albums and EPs under the Jelly Roll name, the attorney for Jellyroll has persisted, stating, "Despite his receipt of a demand to cease and desist using plaintiff's registered service mark, defendant has ignored this demand and continues to use plaintiff's registered service mark knowing that it continues to irreparably harm plaintiff but has nevertheless callously disregarded the rights of plaintiff to his own service mark." It looks like Jelly Roll is in no hurry to give up the moniker.