Rapper turned unlikely country music star coming to Rupp: Who exactly is Jelly Roll?

On one of the many tunes from his new “Whitsitt Chapel” album recounting the reckonings of a scorched earth soul on a lost stretch of backroad, Jelly Roll appears wary of salvation — or at least any form of it that comes with conventional conversion.

“I see your fire and brimstone, that billboard sign on the road,” sings the Tennessee artist, one of country music’s more unlikely crossover stars of recent years. “But you can’t scare me to heaven with gasoline on my soul.”

With a voice of rusted iron resolve, Jelly Roll furthers a notion of spiritualism found in the backyard — way, way back in the yard — of the church settings many Nashville artists flock to openly in their songs and press releases.

“I’ve known to find my kind of people that ain’t at home underneath church steeples,” he confides. “You’d be surprised the places I find Jesus.”

The title of the song in question is, quite fittingly, “The Lost.”

From rapper to Nashville favorite

At the age of 38, the artist born Jason Bradley DeFord defies almost every norm of even the most stylistically broad-minded performers who have veered into country territory. Where many new generation Nashville stars have appropriated accents of hip-hop as bait for young audiences, DeFord was a fully-evolved rapper who lived deep in the culture, eventually facing the consequences and incarceration summoned when the extremes of a street life tripped him up.

Perhaps what empowers the music of “Whitsitt Chapel” and its crossroads journey into country is the way DeFord’s hip-hop beginnings so authentically inform his songs with the restlessness and spiritual upheaval that have sat at the heart of country’s darkest, most earnest roots. And make no mistake. DeFord is no rapper masquerading in a different genre as a lark. The longing in both the voice and lyrics of “Son of a Sinner,” a breakthrough country single that pre-dated “Whitsitt Chapel,” is as plain-speaking, poetic and heartbreaking as a Hank Williams tune. Seriously.

“I’m only one drink away from the devil, I’m only one call away from home,” DeFord sings in a voice that reflects remarkable country temperament and timbre for an artist reared in rap. “Yeah, I’m somewhere in the middle. I guess I’m just a little right and wrong.”

The song went double platinum in sales, became a Top 10 country hit and a Top 40 fixture on the all-genre Billboard Top 100 charts and earned DeFord three Academy of Country Music awards (all for the tune’s music video) last spring when many of the Nashville elite in the audience likely knew next to nothing about him.

How he ended up in country music

If one of country music’s essential dues-paying demands was rising to stardom out of adversity, than the artist now known as Jelly Roll would be an even bigger deal than he already is. A one-time drug addict and dealer, he spent his late teens and early 20s jailed in juvenile and eventually adult correctional facilities for robbery and drug possession charges. His devotion to hip-hop bypassed the bling, however, and found DeFord selling mixtapes out of his car.

The country defection would be gradual to the point of glacial — a process that took roughly 12 years. The 2020 single “Save Me” set the path, “Son of a Sinner” set it on fire and “Whittsitt Chapel” (named for the Antioch, Tenn., church where DeBord was baptized mere months before his first arrest) set it in stone.

His summation of the album in press releases was succinct: “Real music for real people with real problems.”

And image? DeBord is as far afield from pin-up, bro-country polish as a Tennessee artist can wander, possessing a massive bodily profile with enough facial tattoos to rival Post Malone and Lil Wayne. Yet he cuts to a country component in his songs that glammed-up contemporaries often sidestep, even the ones with the occasional taste for salvation. The deepest Jelly Roll songs confront the darkest country topic of all: Guilt — the kind one has to confront and eventually be exonerated from in order to properly convey.

In one extraordinarily revealing lyric from “Halfway to Hell,” the leadoff tune to “Whittsitt Chapel,” DeBord references one of the most beloved of country gospel works, but bends its spiritual sentiment to where it purposely collides with his own sense of unrest and urgency.

“This little light of mine,” he sings, “damn near burned me alive.”

Jelly Roll with Yelawolf and Struggle Jennings

When: Oct. 10 at 7 p.m. Oct. 10

Where: Rupp Arena

Tickets: $59.75-$257.50 on Ticketmaster.com.