Until recently, Jelly Roll was unable to book shows outside of the U.S. due to legal restrictions on travel by former felons.
Tell me why!
During his Toronto debut on Wednesday, Jelly Roll brought out AJ McLean of the Backstreet Boys for a surprise performance of the boy band's iconic 1999 single "I Want It That Way."
In a clip of the performance circulating on X (formerly Twitter), it's almost hard to hear what's happening because the sold-out house roars with applause the second Jelly Roll welcomes McLean to the stage. He exclaims, "Get on out here, AJ. Let’s sing some music for these motherf**kers in Toronto, baby!" before greeting him with a big hug.
As the bright lights turned blue, the crowd sang along at the top of their lungs when McLean started with his "yeah-eh-eh" intro, with Jelly Roll joining in perfect harmony on the first verse, singing, "You are my fire/The one desire/Believe when I say/I want it that way."
Jelly Roll's gig at the 2,500-capacity venue History was a part of his first-ever international swing of shows. The "Save Me" singer announced his first international shows last month. He had not previously booked any dates in Canada or overseas due to visa restrictions tied to arrests and convictions earlier in his life.
On Monday, Jelly Roll performed at the Meridian Center in St. Catharines, Ontario, Canada, benefiting the Heather Winterstein Foundation. The following day, he performed at the 30th annual Ottawa Bluesfest.
Prior to booking his first international tour, Jelly Roll shared with Jon Bon Jovi for Interview Magazine that he was encountering some difficulties booking international tour dates due to his felony convictions.
"I'm so excited. We're figuring out the final pieces of some legal puzzles for me to get overseas," Jelly Roll told Bon Jovi, who responded with confusion. "Yeah. It's funny, America has finally agreed to let me leave and give me a passport, but some countries won't let me come because of my felonies."
Jelly Roll added, "We're working on that. I think it's going to work in my favor."
The country star -- whose real name is Jason Bradley DeFord -- has previously said that he's been to jail some 40 times over the years. He was notably arrested at 16 for aggravated robbery and at 23 for drug dealing.
Jelly Roll has openly discussed his past issues with the law and drugs. He even sat before a Senate committee hearing on Capitol Hill in January to discuss the fentanyl crisis in a move many have viewed as yet another example of how the formerly struggling artist has completely turned his life around.
Jelly Roll returns to the U.S. soon for his next tour. The Beautifully Broken Tour kicks off Aug. 27 in Utah and ends Nov. 23 in Florida. Joining Jelly Roll on tour are Warren Zeiders, Alexandra Kay, ERNEST, Shaboozey and Allie Colleen.
ET spoke to Jelly Roll at CMA Fest last month, and he teased his latest music era, which will follow the success of his last album, 2023's Whitsitt Chapel.
"This has been my whole life the last 11 months," he teased to ET. "I have been drowning in this album. I've never wrote more songs. I've never took it more serious and I'm probably gonna release more music this year than I've ever released in a year of my career."
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