Jelly Roll has been enjoying huge success as a crossover act for the past year or so, but it might never have happened had it not been for some words of encouragement from Lil Wyte.

The multi-genre phenomenon (real name Jason DeFord) who started out as a rapper in Tennessee’s underground Hip Hop scene broke the record for longest reign on Billboard‘s Emerging Artist chart earlier this month. Topping the chart for a record-breaking 25 weeks, he took the title from NLE Choppa who originally set the record with a 24-week run at the top of the chart in 2019 and 2020.

Helping Jelly Roll to achieve this feat were his country/rock-leaning singles “Dead Man Walking,” “She,” “Need a Favor,” and “Son of the Dirty South.” However, his biggest record is the heartfelt and vulnerable “Son of a Sinner,” which became his first chart-topper on the Country Airplay chart last month.

Although the majority of his success is a result of his towering, fervor-stricken vocals, Jelly Roll wasn’t a fan of his singing voice when he first started to experiment with it on record.

It wasn’t until Three 6 Mafia affiliate Lil Wyte pointed out how good it was during recording sessions for Year Round, the 2011 Hypnotize Minds album the pair put out as SNO — a trio of white rappers which also included the late BPZ, who passed away in 2022 — that he began to feel more comfortable with it.

“I had this big record on [Year Round] called ‘Pain No More’ that I wrote in jail,” Jelly Roll explained to HipHopDX. “When I came home it was one of my go-to songs. The first studio session I had with [Three 6 Mafia’s DJ] Paul and them, they were like, ‘What have you got from jail?’ I had this big stack of raps but they wanted to know if I had any songs; I sang that one.”

It was then that Wyte turned to Jelly Roll, blown away by what he had just heard, and told him that he should keep heading in that direction with his art.

“I’ll never forget Wyte looking at me and going: ‘That’s what you need to do,'” Jelly Roll recalled. “I didn’t think I sounded good. I was so self-conscious of it and was like, ‘Nah, I’m not a singer, I’m a rapper.’

“Wyte was one of the first guys that would point back at all these other records where I was singing choruses. ‘You’re singing right here, though. You’re singing right here.’ And I was like, ‘No, I’m just kinda harmonizing.’ I didn’t know anything about music so I was like, ‘Nah, I’m just harmonizing.’ Now I know what a harmony is and it’s the opposite of what I was doing.”

He continued: “I think I then started tinkering with it and started getting more and more comfortable with it as the years went on. It’s just like anything else, the more I did it, the better I felt about it. After the SNO album, I started putting one song with me singing on every album.”

For years Jelly Roll continued to pepper his albums with the occasional singing track. It was his 2020 track “Save Me” that proved to be the “big turning point,” when he decided he was going to go all in and release more songs with him singing.

Jelly Roll and Lil Wyte have known each other for years. Prior to teaming up for SNO, the pair had been booked for some the same shows and hung out a few times. “We were cool but we weren’t what we are now,” Jelly Roll told DX. “To this day, Wyte is one of my best friends.”

Their journey to brotherhood began after Wyte reached out to Jelly upon his release from jail in 2009, after he uploaded his “10 Minute Freestyle” to YouTube.

“I had just got out of jail, and I had put up the ’10 Minute Freestyle’ on YouTube and Wyte was the first person to call me,” Jelly Roll remembered. “He was like, ‘You’re home?’ I was like, ‘Yeah, I’m home.’ He was like, ‘I’m driving up to Nashville right now. I’m starting my own record label with [DJ] Paul and Juicy [J]’s blessing; they’re producing my new album. I wanna help, like immediately.’ And this was when Wyte was on fire.

“So he came up to Nashville and he sat down and was like, ‘Yo, look man, Paul and Juice are in a place now where they’re kinda moving on, they’re getting into other ventures; so they let me have autonomy but with their backing still. So I’m gonna start my own label and put out my own projects.”

He continued: “Paul and Juice wanna do this record called SNO. Project Pat’s got an artist named BPZ — by the way, rest in peace BPZ. He passed away last year — He said, ‘This is how they wanna start it and then I wanna work with you,’ and I was like, ‘Dope.'”

Once Wyte got to Nashville the pair went straight to the studio and recorded their ‘Pop Another Pill’ collaboration. Wyte also hopped on “Hand to the Sky,” a record Jelly had done with Jackson, Mississippi rapper Fat Boy, which ended up on Wyte’s Cocaine & Kush 2 compilation.

“We were just rotating,” Jelly Roll said of his collaborative efforts with Wyte. “I ended up moving down to Memphis and we ended up touring together, and I lived with him in Cordova for probably two years.”

In addition to SNO, Jelly Roll and Lil Wyte also put out two joint albums: No Filter (2013) and No Filter 2 (2016).

Jelly Roll On The Importance Of Tech N9ne: ‘His Energy Is So Pure’

Jelly Roll On The Importance Of Tech N9ne: ‘His Energy Is So Pure’

Working with Three 6 Mafia was a full circle moment for Jelly Roll. Growing up in Nashville, he would listen to all the Memphis mixtapes making their way into the city, by way of his big brother, many of which were by Triple Six.

“We would get all the Memphis mixtapes and the Nashville rap mixtapes,” he explained. “So like Pistol, Haystak, Kool Daddy Fresh, Quanie Cash, they were kinda the big rappers here in Nashville. And then Three 6 Mafia, 8Ball & MJG and Yo Gotti were the big rappers out of Memphis.

“[Street Flavor Records founder] Sonny Paradise and Haystak was getting distribution through Select-O-Hits; so we’d go down to Select-O in Memphis and get all the Underground Kingpin Skinny Pimp shit — all the shit that wasn’t even making it out of Memphis yet. Then I got into Houston rap shortly thereafter and that was the beginnings of the pillars of my sound.”

Asked about his time spent with Three 6 Mafia, Jelly Roll didn’t want to divulge too much about their fabled madcap antics, but he did admit to having some of the “wildest nights” of his life with the legendary Memphis collective.

“Keep in mind we were with ’em right at the peak of like, winning the Oscar. It was — they would takeover bars, like literally,” he said. “They would turn a bar into their living room, anywhere they went. I think that depicts it the best.”