3 Jelly Roll Albums That Led Him Closer to Country and ‘Whitsitt Chapel’

Before the release of Jelly Roll‘s 2023 album, Whitsitt Chapel, and the rapper’s groundbreaking entry into country music, the Nashville-born singer and songwriter was already inching closer to the genre in prior years.

Born Jason Bradley DeFord on December 4, 1984, in Nashville, Tennessee, Jelly Roll — a nickname first given to him by his mother —started releasing mixtapes in 2003. Later, he’d go on to release a number of collaborative albums with friends and rappers Lil Wyte, Haystack, and Shooter Jennings.

Whitsitt Chapel featured collaborations with Miranda Lambert, Ashley McBryde, HARDY, Lainey Wilson, and Brantley Gilbert, among others. The album debuted at No. 1 on Billboard‘s Top Rock & Alternative Albums chart, No. 2 on the Billboard Country Album chart, and peaked at No. 3 on Billboard’s 200 chart. Preceded by singles “Need a Favor” and “Save Me,” featuring Lainey Wilson, the album plays through themes of sin, redemption, and hope.

“This album is about growth and gratitude happening in my life,” Jelly Roll told American Songwriter in 2023. “I wanted to create a project that felt hopeful. I believe the worst feeling a person can have is feeling hopeless or worthless. Therapeutic music. Real music for real people with real problems.”

[RELATED: Who Is Country Music’s Biggest New Star, Jelly Roll]

Though Whitsitt Chapel is evidence of Jelly Roll’s place in country, his previous body of work as a rapper also captures the fuller scope of the multi-faceted artist, in addition to a number of releases that saw him steadily crossing over.

Here’s a look at three albums, including a collaborative series, that led Jelly Roll to Whitsitt Chapel.

1. Waylon & Willie — Waylon & Willie IV (2017 – 2020)

In 2017, Jelly Roll collaborated with friend and rapper Struggle Jennings on a Waylon & Willie album, an homage to the decades-long musical partnership of the outlaw country legends Waylon Jennings and Willie Nelson. The two country legends collaborated on several albums together, including their 1978 debut together, Waylon & Willie, before Jennings’ death in 2002.

The first release led to a series of four albums by Jelly Roll and Struggle Jennings, who is the step-grandson of Waylon Jennings and the nephew of Shooter Jennings. All four albums are their ode to outlaw country, through hip-hop.

[RELATED: The Outlaw Marriage Between Waylon Jennings and Willie Nelson]

“We just released ‘Waylon and Willie 4,’” wrote Jelly Roll after releasing their fourth install,ment in 2020. “This album, in fact, this entire series is so much deeper than music for us it’s an accumulation of decades of friendship and brotherhood. Hardships, up and downs, laughing to the point of crying, crying to the point of laughing, carrying caskets together, collect calls, court dates, visits through sheets of glass. Struggle saying ‘Free Jelly’ while I was locked up, me saying ‘Free Struggle’ while he was locked up. Life changes, arguments, celebrations. I could go on forever. This album is a testament to overcoming obstacles and beating the odds.”

2. Self Medicated (2020)

Jelly Roll’s 2020 album Self Medicated saw him begin to dig deeper into the singer/songwriter arena. The album, which features Struggle Jennings (“Afraid of Me”), was also the first introduction to his soulful ballad “Save Me,” which he would revisit three years later as a duet with Lainey Wilson. “Save Me” was written in the middle of the pandemic, when Jelly Roll knew he needed to write, and make music, following the death of his father — to save himself.

When Jelly Roll first premiered the video for the song in 2020, he stated that the song was a bit of a departure for him from the more revealing track — Somebody save me, me from myself / I’ve spent so long living in hell / They say my lifestyle is bad for my health / It’s the only thing that seems to help.

“This one is a little bit of a curveball for me,” wrote Jelly Roll in the YouTube descriptor. “I don’t usually do these stripped-down acoustic videos, but writing this song made me feel something and I felt y’all needed some insight into the more vulnerable side of the music business.”

3. Ballads of the Broken (2021)

Prior to the release of Whitsitt Chapel, Jelly Roll was already dipping into country with Ballads of the Broken, in 2021. Just two years later, Jelly Roll won three CMT Music Awards for the single “Son of a Sinner,” the artist’s first single released within the country music format.

The song is one of the few country-leaning tracks on the album. It peaked at No. 8 on the Billboard Hot Rock & Alternative Songs chart and went to No. 1 on the Country Airplay chart. The song’s success inspired Jelly Roll to go full-in with country music.

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