Jelly Roll brings message of musical inspirations By: Eva Wasney Posted: 11:17 PM CDT Monday, Mar. 17, 2025 Last Modified: 6:37 PM CDT Wednesday, Mar. 19, 2025 Updates

Cowboy hats, four-leaf clovers and too many covers.

Nashville country-rap superstar Jelly Roll made his Winnipeg debut on Monday night, performing to a sold-out St. Patrick’s Day crowd at Canada Life Centre.

The evening was a celebration of the healing power of music. But instead of focusing on their own offerings, the headliner and openers paid more mind than necessary to their artistic influences.

Following an inspirational, intention-setting message, the Jelly Roll took a long walk through the floor — hugging and high-fiving concert goers along the way — to a satellite stage, performing I Am Not Okay underneath a floating set piece made to look like the frame of a burning house.

There was lots of fiery pyrotechnics — including a piano played aflame — and essence of brimstone during the God-fearing musician’s 90-minute performance in support of his latest studio album, Beautifully Broken.

Jelly Roll, given name Jason DeFord (his stage moniker is a childhood nickname from his mom), is a 40-year-old country artist and ex-con who trades in ballads about overcoming addiction and his troubled past, rather than trucks and beer.

The personal content of his genre-blending music has earned him widespread appeal since rising to mainstream prominence following the release of Son of a Sinner in 2021. Jelly Roll now has four Grammy nominations to his name and last month, was tapped to pay tribute to Johnny Cash with a cover of I Walk the Line during Saturday Night Live’s 50th anniversary special.

While there were more than a few crowd members sporting leprechaun hats and green attire on Monday night, Jelly Roll played a different kind of Man in Black and stuck with his usual uniform: a black work shirt, heavy chain and a black baseball cap, worn backwards above his heavily tattooed face.

The only indication of the Irish holiday was an occasional flood of green lighting and a somewhat rowdier-than-usual Monday audience.

With his booming voice and larger-than-life stage presence, Jelly Roll frequently took on the stylings of a charismatic preacher, offering nuggets of inspiration and aspiration between songs new and old. A massive glowing rosary descended from the rafters during Need A Favor, a breakout hit from his 2023 album Whitsitt Chapel.

The mega church vibes were punctuated by a backing chorus and a massive stage topped with video screens and a golden curtain.

While Jelly Roll burned through a range of originals new and old — such as Creature, Wild Ones and Liar, which has spent the last five weeks at the top of Billboard’s country chart — he spent a lot of time covering other artists, from Eminem to Garth Brooks to Green Day.

Paying homage is one thing, but for a headlining artist with 10 studio albums to perform multiple cover medleys is disjointed at best and disappointing at worst.

At press time Jelly Roll was performing under a shower of rain while confetti floated down from the ceiling.

The cover-heavy party started 10 minutes late with a sleepy opening set from Florida country artist Savannah Dexter, who wandered around the stage and attempted to ingratiate herself to the Canadian crowd with an ironically ill-executed singalong of Shania Twain’s Don’t Impress Me Much.

The energy ramped up slightly with the arrival of Dexter’s husband and collaborator Brabo Gator. For the remainder of their set, the pair performed a few bland love songs and bopped around to snippets of hits by other artists. We’re not talking covers here, just dancing to radio tracks while encouraging the audience to sing along. It was a weird start.

A pair of hype-DJs, dubbed the Arena Rockerz, filled the gap between acts with two sets of rushed rap, country, classic rock and far too much call-and-response.

The musicianship and pacing improved with Josh Ross, an ascendant Canadian country star who performed at the 2022 Grey Cup halftime show alongside members of Florida Georgia Line following the release of his breakout hit First Taste Gone. The Hamilton-born singer-songwriter last appeared at Canada Life Centre two years ago as an opener for Nickelback.

Wearing a camo trucker hat and green John Deere hoodie, Ross and his band (also trucker hatted) played some new and original music — such as Trouble and Single Again — but still dedicated a big chunk of their half-hour set to covers, including closing with Iris by the Goo Goo Dolls.

eva.wasney@winnipegfreepress.com