Jelly Roll showed off his dramatic weight loss at the Pre-Grammy Gala ahead of the 2026 Grammy Awards. The country singer, who once weighed roughly 550 pounds, appeared nearly unrecognizable as he walked the red carpet at approximately 265 pounds, as he told Men’s Health in a profile earlier this month. He later took the stage to perform a tribute to late rocker Ozzy Osbourne. The “Winning Streak” singer has frequently spoken about his lifelong relationship with weight, revealing that his nickname Jelly Roll stems from being a self-described “chubby kid.” “I’ve been fat my whole life,” he said on “The Bobby Bones Show” in 2022, noting that his mom gave him the nickname as a child. “She started calling me Jelly Roll when I was young, and I spent the next 20 years trying to grow into the name.” On the “Dumb Blonde Podcast,” hosted by his wife, Bunnie Xo, the singer described his commitment to improving his health since beginning his weight loss journey in 2022, and why he’s been so open about the process. “What I want the world to know, and I want people to see … is that I didn’t become successful because of my weight. I became successful in spite of it,” he said. “I somehow managed to be this successful carrying 550 pounds. That’s insane.” This year, the 41-year-old artist earned three Grammy nominations, one of them for Best Contemporary Country Album for “Beautifully Broken.” ...read more read less