Judging by Jelly Roll‘s colossal 2024 so far, 39 is definitely the new 19. The “Save Me” country star who spent his teenage years and twenties rolling in and out of lockup for a variety of charges has seriously been making up for lost time since January. With an infectious joy and gratitude infusing everything he does, the Tennessee rapper-turned-singer (born Jason DeFord) has crammed a lifetime (or two) or career highlights and firsts into the past nine months.

He capped that annus mirabilis with a rare quadfecta last weekend, which kicked off with his first-ever gig at Madison Square Garden in New York (which was sold out), followed by a headlining slot at the Global Citizen Festival, a musical guest spot on the season 50 premiere of Saturday Night Live and a performance and debut couch visit on Monday night’s (Sept. 30) The Tonight Show Starring Jimmy Fallon.

That is just a sliver of the high points Jelly has achieved this year. Check out Billboard‘s month-by-month breakdown of Jelly’s epic 2024 roll so far.

January

Jan. 1 — Nothing says “it’s gonna be a good one” more than ringing in the New Year with Dick Clark’s New Year’s Rockin’ Eve With Ryan Seacrest. Technically this one belongs in the 2023 column, but we’ll fudge it because Jelly helped usher in his monumental 2024 by headlining the biggest NYE gig alongside Megan Thee Stallion, Renée Rapp, Green Day and others.

Jan. 7 — In a testament to the former Billboard Country Power Players cover star’s rising profile, he stopped by CBS News Sunday Morning to revisit his former jail cell at Metro-Davidson County Detention Facility in Nashville to reflect on how far he’s come. “There was a time in my life where I truly thought this was it,” the singer said, growing emotional. “And then, coming here after being nominated for two Grammys just hits different.”

Jan. 11 — In keeping with his giving back vibe, JR testified in front of the U.S. Senate Banking, Housing and Urban Affairs committee on behalf of the FEND Off Fentanyl Act to describe the devastating toll that fentanyl has had nationally and in his community. “I’ve attended more funerals than I care to share with you all on this committee. I could sit here and cry for days about the caskets I’ve carried of people I loved dearly, deeply in my soul, good people, not just drug addicts,” he said. “Uncles, friends, cousins, normal people, some people that just got in a car wreck and started taking a pain pill to manage it.”

February

Feb. 2 — The singer was part of the all-star crowd who paid tribute to Jon Bon Jovi at the 33rd annual MusiCares Person of the Year gala, growling out a version of BJ’s “Bad Medicine” — while also continuing to spread the word about the nation’s fentanyl problem via a jacket featuring sobering facts about drug addiction.

Feb. 3 — You know you’ve arrived when Clive Davis invites you to perform at his legendary pre-Grammy gala. Jelly stunned the room with “Need a Favor” and “Save Me” in front of A-listers Mariah Carey, Meryl Streep, Lenny Kravitz, Gayle King, Shania Twain and many more. Though he didn’t win for best new artist at the Grammys the next night, in this case just being nominated was definitely well-deserved and right on time.

Feb. 4 — In a year when he met so many of his heroes, after getting introduced to his longtime crush Taylor Swift at the 2024 Grammy Awards, even Jelly’s wife, Bunnie XO, had to give it up. “When your hubby gets to meet his crush finally,” Bunnie wrote over a TikTok she shared of the country star’s encounter with the 14-time Grammy winner. “Crazy moment,” Jelly commented on Bunnie’s post before making it clear he only has eyes for her. “love my wife so much.”

Feb. 11 — Jelly landed a spot in an Uber Eats Super Bowl “Need a Favor” ad, which debuted during the big game. Joking about his many face tattoos, the singer also proved he had pretty decent acting chops. He also appeared in a more serious Super Bowl ad taking on the outrageous cost of healthcare alongside Lainey Wilson and Valerie June.

Feb. 18 — The awards kept coming with a W over Chris Stapleton, Cody Johnson, Luke Combs, Morgan Wallen, Zach Bryan, HARDY and Kane Brown for the male country artist of the year at the 2024 People’s Choice Awards.

April

April 1 — Jelly brought the crowd to its feet at the 2024 iHeartRadio Music Awards during a candle-lit performance of his Lainey Wilson duet “Save Me.” He also took home the best new artist (pop) and best new artist (country) awards and gave a moving speech that left the audience stunned. “You don’t know what it means to a kid like me. What does it mean when a guy like me has the opportunity to be the new pop artist of the year?” he said. “It means that God will always use the least likely messenger with the biggest message, every single time. I love you, Jesus, and I love you, Bunnie, my wife.”

April 7-8 — Jelly served as a guest celebrity mentor on American Idol for the show’s annual pre-Hollywood Hawaii boondoggle, sharing the sage advice he gave his young charges. “I wanted to make sure they were present. Sometimes you’ll be in the middle of something and won’t take the time to see it. You just hope they see it,” said the singer who knows all about savoring the moment. Not for nothing, departing judge Katy Perry also recommended him to fill her slot.

April 7 — Chalk three more trophies up for Jelly thanks to his trifecta at the 2024 CMT Music Awards, where he went three-for-three with wins for video of the year and male video of the year (“Need a Favor”), as well as CMT performance of the year for his 2023 CMT Music Awards performance of “Need a Favor.”

April 13 — After tipping the scales at more than 500 pounds in 2015, Jelly revealed that he’d lost 70 pounds while training for comedians Bert Kreischer and Tom Segura’s May 7 2 Bears 5K charity run. “I feel really good. I was thinking, I plan on losing another 100, 100-and-something [pounds],” he said. “If I feel this good down this weight, man, I can only imagine what I’m going to feel like by the time I go on tour.”

April 24 — One of Jelly’s hip-hop heroes, Public Enemy’s Flavor Flav, came to the singer’s defense after trolls got at him so hard that the “Save Me” star decided to quit social media. “How dare y’all try to judge my man about his weight and his character,” the rapper said. “This man is winning awards for his music. This man’s music has given a lot of people hope.”

April 26 — Paying tribute to recently departed country icon Toby Keith, Jelly performed Keith’s “Should’ve Been a Cowboy” during his first evening set at the Stagecoach Festival alongside T-Pain in an appearance that also featured guests Ernest and Maddie & Tae.

May

May 16 — In keeping with what he’s quickly established as an expectation of excellence for awards show performances, Jelly Roll debuted his emotional new single, “Liar,” at the 2024 ACM Awards, where he was up for entertainer of the year, male artist of the year, single of the year (“Need a Favor”) and music event of the year (“Save Me” with Lainey Wilson). He won the lattermost, and gave one of his patented emotion-packed acceptance speeches. “This song saved me,” he told the crowd with tears in his eyes. “I was in a dark place. I thought I would die and go to jail, and I’m standing here today an ACM Awards winner.”

May 21 — In another preview of new music, Jelly Roll debuted the vulnerable track “I Am Not OK” on the season finale of The Voice.

June

June 6 — In a year when Jelly Roll met and collaborated with many of his musical icons, his spot crooning “Sing For the Moment” with his “childhood hero” Eminem at the all-star Michigan Central Station re-opening was an all-time moment. Discussing the special moment on Howard Stern’s SiriusXM show (another bucket list item, see below), the singer said it was surreal. “They called back and was like, ‘Eminem wants to know if you would sing a song with him,’” he told Stern. “I get goosebumps up my body. I was like, ‘Dude, I’m so in.’” The lifetime high water mark rose to a new level a month later when Jelly appeared on the song “Somebody Save Me” (which samples his hit “Save Me”) from Eminem’s The Death of Slim Shady album; he also appeared in the song’s video.

June 11 — Jelly signed a worldwide deal with Republic for distribution of his new single, “I Am Not Okay,” as well as for his at that time not-yet-untitled next album. The deal also included plans to expand his music across multiple genres and market him in new territories. He made his first visit to Howard Stern’s SiriusXM show the next morning, where he debuted “I Am Not Okay” and covered Otis Redding’s “(Sitting On) the Dock of the Bay” and Hootie and the Blowfish’s “Let Her Cry.”

June 13 — Continuing to fill his bucket, Jelly hung out with Sylvester Stallone on the set of his TV drama Tulsa King, where they celebrated the singer’s fourth No. 1 hit on Billboard’s Country Airplay chart for “Halfway to Hell.”

June 18 — After patiently waiting, Jelly Roll excitedly announced his first-ever international tour dates with a pair of Canadian shows after revealing that he’d been unable to book shows outside the continental U.S. due to his past felony convictions. He celebrated the landmark a month later at the first show in Toronto when he was joined by the Backstreet Boys‘ AJ McLean for a run through the boy band’s 1999 single “I Want It That Way.”

July

July 13 — Of course he got slimed at the 2024 Kids’ Choice Awards, where he was also a nominee and presenter.

July 16 — WWE chief content officer Paul “Triple H” Levesque announced that Jelly Roll would provide the official theme songs for the Aug. 3 SummerSlam event in Cleveland via his tracks “Liar” and “Dead End Road,” the latter from the all-star Twisters soundtrack. The dream came full circle three weeks later when Jelly stepped into the ring and teamed with Miz and R-Truth to deliver a chokeslam on Austin Theory. Jelly’s new single, “Get By,” was also chosen by ESPN as the anthem for it’s 2024-2025 college football coverage.

July 26 — Ending a yearslong feud, Jelly teamed up with Machine Gun Kelly (call them KellyRoll) for the two-years-in-the-making John Denver-interpolating “Lonely Road.” The emotional video for the song — featuring Jelly’s wife Bunnie and MGK’s partner Megan Fox — took on wife Bunnie’s struggle with infertility.

July 27 — From offender to official, Jelly cut the ribbon on the new Jelly Roll Music Studio at Genesee County Jail in Flint, MI and got sworn in as a deputy with the Community Cares Task Force.

August

August 16 — The singer’s name was on the track list for Post Malone’s all-star debut country album, F-1 Trillion, with their track “Losers” taking its place alongside Posty’s country superstar collabs with Morgan Wallen, Blake Shelton, Luke Combs, Tim McGraw, Hank Williams Jr., Dolly Parton and many more.

August 17 — He kept rolling along with a performance at Stephen Talkhouse in Amagansett, N.Y. for an audience that included Jimmy Fallon, tennis great John McEnroe and Jon Hamm, and an introduction from Smartless podcast hosts Will Arnett, Jason Bateman and Sean Hayes.

August 23 — Jelly announced the title and release date for his anticipated Whitsitt Chapel follow-up, Beautifully Broken, due out on Oct. 11. He then hit the road for the four-month Beautifully Broken U.S. tour on Aug. 27 with guests Warren Zeiders and Alexandra Kay.

August 28 — He joined Tyler Hubbard and Jordan Davis for a cover of “Red Solo Cup” for the NBC concert special Toby Keith: American Icon.

September

Sept. 5 — In one of his biggest bookings to date, Jelly landsed his first headlining slot at the Stagecoach Festival in Indio, CA on the 2025 roster that will also include Zach Bryan, Luke Combs and Lana Del Rey.

Sept. 11 — The “pinch me” moments kept coming with Jelly joining Eminem for an iconic performance of “Somebody Save Me” at the 2024 MTV VMAs.

Sept. 15 — Proving his versatility and emotional depth once again, Jelly made his Emmy Awards debut by singing “I Am Not Okay” during the somber “in memoriam” segment, accompanied by a string section.

Sept. 19 — Already super-booked, Jelly added another gig to his roster when he was announced as one of the headliners — along with Kane Brown — for the New Year’s Eve Live: Nashville’s Big Bash concert from Music City’s Bicentennial Capitol Mall State Park.

Sept. 25 — As if it even needs to be said, of course Jelly Roll was on the list of performers and presenters who will help induct the class of 2024 Rock and Roll Hall of Fame inductees, alongside such luminaries as: Busta Rhymes, Dr. Dre, Demi Lovato, Dua Lipa, James Taylor, Roger Daltrey, Slash and The Roots.

Sept. 26 — After winning best new artist at the 2023 People’s Choice Country Awards, Jelly took home the crossover song of 2024 trophy for his MGK collab “Lonely Road.” The next night, he headlined his first-ever show at New York’s Madison Square Garden.

Sept. 28 — The singer made his Saturday Night Live debut with moving performances of “Liar” and “Winning Streak” on the season 50 opener, where he also made his acting debut in a cut-for-time House of the Dragon spoof in which he played Lord of the Rings‘ Samwise Gamgee to guest Andy Samberg’s equally out-of-place Legolas. That same night, Jelly Roll also co-headlined the 2024 Global Citizen Festival in New York’s Central Park.

Sept. 30 — How do you cap off a truly epic nine month run? By performing an unforgettable version of “Lonely Road” with guests MGK and Travis Barker on The Tonight Show, while also celebrating your first sit-down couch time with host Jimmy Fallon.