There aren’t many former drug addicts and felons who become white rappers only to transition in their late 30s to country music.
But that’s exactly what Jelly Roll has done over the past couple of years, becoming one of the most beloved country music artists in the world today in the process.
And jaws hit the floor when country star Jelly Roll revealed a secret about meeting the rapper Diddy.
Jelly Roll, whose real name is Jason DeFord, began his music career in 2010 as a white rapper who sold his mixtapes out of the trunk of his car to try and make ends meet.
And for over a decade, he fought to build a career that ultimately allowed him to obtain custody of his young daughter and support his family like never before.
But Jelly Roll knew he was capable of even more and inevitably returned to his Tennessee roots by attempting to transition to country music, making his first Grand Ole Opry appearance in November 2021.
His debut country single, Son of a Sinner, was released in January 2023 and immediately skyrocketed up country music charts, ultimately becoming the number one song on country radio in the nation and spending a record-breaking 25 consecutive weeks at number one on Billboard’s Emerging Artists chart.
Less than three months after Son of a Sinner was released, Jelly Roll won CMT Awards for Male Video of the Year, Male Breakthrough Video of the Year, and Digital-First Performance of the Year, went on to be nominated for a Grammy, and even beat out new country music powerhouse Zach Bryan for the CMA’s New Artist of the Year – all less than a year after his debut single was released.
In January, the 39-year-old used the platform he’s built through his music to testify before Congress in support of anti-fentanyl legislation – a cause near to him due to his own personal struggles and those of others close to him.
As a former drug addict and dealer, Jelly Roll offered a unique perspective on the fentanyl crisis, telling Congress, “I was a part of the problem, but I am here now, standing as a man [who] wants to be a part of the solution.”
The music sensation recently appeared for a sit-down interview on the popular CANCELED podcast with YouTuber Tana Mongeau, in which he shared a jaw-dropping story about meeting the rapper Diddy when they both were guests on Jimmy Kimmel’s show.
In March, Homeland Security officials raided Diddy’s residences in connection to a sex-trafficking investigation.
According to the Tampa Bay Times, Diddy, whose real name is Sean Combs, allegedly held “sex parties so brutal that the young women and men lured into attending them would often vomit and pass out from being drugged, beaten, and raped, sometimes for hours on end.”
The paper also reported that Diddy allegedly filmed these events and used the recording to blackmail other famous people into submitting to his demands.
Jelly Roll had an opportunity to hang out with Diddy after they both appeared on Kimmel’s show, which he recalled as the first time he was in a position to meet a prominent celebrity.
“I will tell this story, and I’ll probably get in trouble for it,” Jelly Roll began. “Not harping on it ’cause it’s a hot topic, but I did Kimmel the day Diddy did Kimmel.”
But after agreeing to meet the rapper at first, Jelly Roll got a feeling in his gut that led him to change course.
“This is the first time in my career, ever, where they said, ‘Do you want to meet such-and-such?’” Jelly Roll recalled. “And I said, ‘Yeah,’ and I started walking that way, and as I was getting down the hallway — this is a true story — I said, ‘Nah,’ and went and got back in the car.”
Jelly Roll said he changed his mind in large part due to a joke he had previously made about Diddy allegedly being the one who had legendary rapper Tupac murdered.
“I don’t know what it was, and I made a joke at first, I was like, ‘Who don’t wanna meet the guy that got Tupac killed?’” Jelly Roll said. “Nobody thought that was funny, so I was like, ‘Ooh that’s a bomb, maybe I shouldn’t go do this anyway.’”
“So I was already skeptical, ’cause I thought I had a funny one,” he added.
Jelly Roll ultimately decided that he did not even want to get his picture made with Diddy, a decision he is now glad he made.
“When we were walking, I was like, I don’t know,” he said, before adding that “very seldom [do] things rub me in a way where I was like, ‘I don’t even know if that’s a picture I want.’”
“I’ve ended up in pictures with people I don’t want to be with,” he admitted.
Needless to say, Jelly Roll’s decision to listen to his gut on meeting Diddy is proving more and more to be the right decision with each passing day.
