Jelly Roll Talks Incarceration, Luck and His Expanding 1st Arena Tour

There’s no doubt about it, Jelly Roll is on a roll. The Nashville-raised rising star has made the incredible leap from prison to No. 1, and assembled millions of fans along the way.

Jelly kept matters humming along when he stopped by Jimmy Kimmel Live! on Tuesday night (June 25) for a glimpse inside his forthcoming Beautifully Broken Tour, his background and how music and family helped turn his life around.

Chatting with Martin Short, who is filling in for Kimmel as guest host, Jelly admitted he’s a lucky guy. “I always say, talent will get you really far but if you don’t have a horseshoe hidden in there somewhere, you could be in a little trouble,” he explained. “Lucky for me, I had a rabbit foot in my butt.”

There was a time when “trouble” could have been Jelly’s middle name. Looking relaxed on the Live! couch, Jelly recounted how he was incarcerated as a juvenile and ended up in the “rotating door” of the system for a decade.

His songwriting flourished when he was locked up, for crimes ranging from aggravated robbery to drug dealing.

“I had a lot of time,” he admits. “I thought, ‘Maybe I should invest this time in something positive.’” His time on the inside left an indelible mark; he got his first face tattoo while incarcerated.

Becoming a father changed his outlook and motivated the Billboard cover star, whose music straddles rock, rap and country. His rags-to-riches moment was the result of “10 years of living in my van and selling mixtapes out of my trunk,” he continued.

On getting his break, he said, “I just did it independently forever. I just kept writing songs, putting them out myself, upload them to YouTube, it started to grow and build.”

Jelly last year achieved a first on Billboard’s charts when “Need a Favor” became the first ever song to have hit the top 10 of both Country Airplay and Mainstream Rock Airplay. He has tasted life at the penthouse, with “Dead Man Walking” (Mainstream Rock Airplay) and “Son of a Sinner” (Country Airplay) topping Billboard charts.

Jelly will play those songs and more when he embarks on his Beautifully Broken Tour late August, which the musician was excited to tell short that he is expanding. “That’s why I’m here!” Jelly said enthusiastically. “I’m here to tell you all that I’ve added 16 shows to my first arena tour to the United States of America — Madison Square Garden … I’m having great week!”

A press release the following morning had a minor correction — the tour is adding 15 new dates instead of the originally stated 16.

The Beautifully Broken tour is slated to kick off on Aug. 27 with a gig at the Delta Center in Salt Lake City and include stops in Seattle, Portland, Los Angeles, San Antonio, New Orleans, Orlando, Boston, New York, Philadelphia, Chicago and St. Louis before winding down with an Oct. 27 gig at the Spectrum Center in Charlotte, N.C.

The newly added dates are:

Watch his late night performance below.