Jelly Roll: “I’ve come a long way in my hotel journey” 

Nashville rapper-turned-country sensation Jelly Roll sits down to talk about his most unforgettable hotel experiences, and it’s clear that he understands the assignment. “We started at Super 8s and Motel 6s, and we’ve graduated our way up to some nicer hotels. It’s been a rough course but I’m telling you, I am qualified to have this conversation—I have seen all of the good, bad and indifferent.”  

Jelly Roll, aka Jason Bradley DeFord, is fresh off a triple win at the CMT Music Awards, taking home more trophies than any other artist. The 39-year-old was also nominated for two Grammys this year, including Best New Artist, plus he was crowned CMA’s 2023 New Artist of the Year. But to call Jelly Roll’s rise to fame “meteoric” would be putting it lightly.  

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In life as in hotels, he’s seen the extremes, with enough heartache thrown in to inspire a full catalogue of country songs. He grew up in the lower working-class Nashville suburb of Antioch, and was in and out of youth detention centers. He battled addiction, and struggled to find his footing as a white Southern rapper.

But then came his viral hit Save Me, uploaded to YouTube in 2020 with no promotional spend behind it. It was among his first forays into country music, a highly personal anthem of hopelessness, addiction, and trouble fitting in. The song resonated, quickly amassing millions of views, blasting him from a struggling artist to a beacon of hope for many (fans often seek him out post-show and tearfully share their own heartbreaking stories, as chronicled in last year’s Hulu documentary Jelly Roll: Save Me). Less than two years later, he sold out his home town’s 15,000-seat venue, Bridgestone Arena, marking a milestone moment for the performer.  

Whether he’s on the road in support of his latest album, Beautifully Broken, or traveling with his kids and wife, podcaster Bunnie XO, Jelly Roll tries to forge the same intimate connections with hotel staff as he does with fans. Case in point, his preferred way to be greeted at check-in is with a friendly embrace. “If I had it my way, everybody gives everybody a hug. I think the world’s missing hugs,” he says. “I like the handshake hug, too. And I’m a big fan of the slapping hug.” 

In terms of hotel hacks, Jelly Roll’s top tip hinges on the same power of connection. “I feel like we’re giving away some serious game here, but here’s my best hack: If you’re ever by the front desk late at night, stop in, say hello. Tell them you’re trying to get a late checkout,” he says. “It’s never failed. Nine out of 10 times the morning person turns down my late checkout—they’re always in a bad mood, they just got to work. But the midnight person will give me a late checkout—100% of the time it’s worked for me.” 

While the multi-platinum singer-songwriter enjoys getting to know hotel staff these days, it wasn’t that long ago that he tried very hard to avoid them. “In our early touring days, we would be so broke that we would sleep in our van outside like [one of the chain inns],” he recalls. “And then when they did the continental breakfast in the morning, we would walk in by the desk and all just rush into the breakfast and leave with as much stuff as we could fit in our pockets—this is how we lived for like three years on tour.” 

Jelly Roll the country star now likes to enjoy his breakfast in a more relaxed setting. “My perfect somewhere would be a vacation with the family, the wife, waking up at the The Royal Hawaiian,” he says. “We’d have breakfast on the balcony looking out at an ocean view—I’m a sucker for a balcony. Right after that, we’d rip four wheelers through that park on the island where they filmed pieces of Jurassic Park and all those movie scenes.” 

His newfound fame has opened the door to other elevated hotel experiences, too. “At the Four Seasons, we order them therapy pillows, man. The big body ones. Got to have a good thread count on the sheets. My wife calls me bougie,” he says. Access to extraordinary hotel amenities has made his job easier, too. “At the Sunset Marquis in L.A. they have studios downstairs; it’s probably the best studio for writing and recording music,” he says. “I could come to L.A. and do a whole album and never leave that hotel. It’s the most rock ’n’ roll.” 

Among his fellow musicians, Jelly Roll seems especially worthy of a little luxury and added hospitality in his hotel stays. While he often says he makes “real music for real people with real problems,” the musician also gives back well beyond the therapeutic nature of his songs: Profits from the Bridgestone concert were donated to fund the building of a recording studio in a Nashville-area juvenile detention center—the same place he did time as a teenager. “Just to reflect, we started at Super 8s and Motel 6s. I told you, I’ve come a long way in my hotel journey.” And it seems he’s come a long, long way in his life journey, too.   

Martina Sheehan

Writer

Martina Sheehan is a Chicago-based travel writer-editor who has written for the New York Times, Condé Nast Traveler, Budget Travel, Forbes Travel Guides, and Time Out guidebooks, among others. She has traveled to 38 countries and 46 states, and never leaves home without a good map app, a themed playlist, and her daughter.