Celebrity Entertainment Booking Agent - Headline Entertainment
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Jelly Roll

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BIOGRAPHy

Jelly Roll

Powerhouse singer, songwriter, and rapper Jelly Roll has staged one of the most remarkable crossover triumphs in modern music history. Born Jason DeFord in Antioch, Tennessee, he spent over a decade building a dedicated underground following by independently releasing a prolific string of raw hip-hop mixtapes and independent independent rock projects. His career shifted dramatically with his 2023 country  debut, Whitsitt Chapel, which launched chart-topping singles like “Need a Favor” and “Son of a Sinner.” His transformation from a struggling independent artist to a multi-platinum, Grammy-nominated superstar was cemented by his vulnerability regarding his past battles with incarceration and addiction. Jelly Roll has captured top honors at the CMA and ACM Awards while solidifying his status as a major mainstream mainstay. Expanding his cross-genre dominance, his hit collaboration “Amen” alongside alternative country trailblazer Shaboozey took home a 2026 Grammy Award. Celebrated for his powerful live shows and deeply moving lyrics, Jelly Roll stands as an inspiring icon of redemption in American popular music.

Career Path

2021Released 'Ballads of the Broken' on BBR Music Group as his major label debut, with lead single 'Son of a Sinner' climbing the Country Airplay chart and 'Dead Man Walking' topping the Mainstream Rock chart.
2023'Son of a Sinner' hit No. 1 on Billboard's Country Airplay chart, giving Jelly Roll his first country radio No. 1 after two decades as a rapper and mixtape artist.
2023Released 'Whitsitt Chapel', his ninth studio album and first country full-length, which debuted at No. 1 on Billboard's Top Rock and Alternative Albums chart and No. 3 on the Billboard 200, featuring 'Save Me' with Lainey Wilson.
2023Earned five CMA nominations as a first time nominee, including single and video of the year for 'Need a Favor', and won New Artist of the Year over Zach Bryan, Parker McCollum, Megan Moroney, and Hailey Whitters.
2024Was nominated for Best New Artist and Best Country Duo/Group Performance for 'Save Me' with Lainey Wilson at the 66th Grammy Awards, capping his breakout debut year as a country artist.
2024Released 'Beautifully Broken', his tenth studio album, which debuted at No. 1 on the Billboard 200, his first career chart topper after Whitsitt Chapel's No. 3 peak the year before.
2024Launched the Beautifully Broken Tour, his biggest headlining run to date, selling more than 550,000 tickets across sold out arena stops including Madison Square Garden and Crypto.com Arena, before wrapping the run at Charlotte's Spectrum Center on October 27.
2025Landed four ACM nominations, including Entertainer of the Year, Male Artist of the Year, and Album of the Year for 'Beautifully Broken', and joined Shaboozey for a performance of 'Amen' at the ceremony.
2026Won three Grammy Awards for 'Beautifully Broken' at the 68th Grammy Awards, including Best Contemporary Country Album, Best Country Duo/Group Performance for 'Amen' with Shaboozey, and Best Contemporary Christian Music Performance/Song for 'Hard Fought Hallelujah' with Brandon Lake.
2026Was inducted into the Grand Ole Opry on March 10 by Lainey Wilson, with Craig Morgan joining the ceremony, becoming the fourth artist inducted during the Opry's centennial celebration.

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WHAT OUR CLIENTS SAY

Ray A.
Scotland, CT
“The services of Headline Entertainment has allowed Scotland Vol. Fire Dept. to be the leader in comedy events in Eastern CT. Headline has provided outstanding talent and gone above and beyond to ensure that our fundraisers are successful.”
Sherry P.
Bolton, MA
“OMG!!!!! We had a blast and nothing but positive feed back for our Youth Football Comedy Night fundraiser. Their acts were hilarious! I will pass your name around to let everyone know of your services.”
The Country Club at Woodmore
Mitchelville, MD
“I would like to take this opportunity to express our satisfaction with the comedians you booked at our Member-Guest Tournament. All of the members in attendance had a wonderful time and those who weren’t were advised as to what they missed. A great time was had by all. The show and professionalism in preparation of the show were both superb.”
Sabrina S.
Mt. Laurel, NJ
“Thank you for booking us Paul Reiser and making sure the event went so well. We appreciate all the time he gave us. Please pass along our heartfelt thanks for an AMAZING evening. People are still retelling his jokes. It was the perfect event!”
Nancy J.
Las Vegas, NV
“I just wanted to let you know how much awesome feedback I have received on Tom Cotter’s performance last night. My attendees are saying he was the best we’ve ever had!!!”
CM Events
Minneapolis, MN
“Johnny, It’s been a pleasure working with you over the years on booking national talent. We appreciate your informed guidance throughout the process from contract to showtime, knowing you’ve got our back. Looking forward to our next show!”
Tom C.
Woodland Hills CA
“I want to personally thank you booking Tom Cotter for us for our State Farm event. His balance of humor and professionalism was a big hit. We appreciate all that you did to make our event a success.”
Matt J.
Washington, DC
“Tom (Cotter), you were the highest rated speaker of the entire meeting! Thanks again for such a great performance!”
The Fulton County YMCA
Gloversville, NY
“Thank you so much for joining us this past Saturday. The show was terrific! I have been stopped numerous times on the street and in offices by people who attended the event, and the comments have been uniformly enthusiastic. They loved you.”
Emmie L.
Washington, DC
“Eric Dittelman was wonderful! The audience really loved him and his performance really made the whole event”
Lou P.
Branchburg, NJ
“Here we are days after our Company Holiday Party and I am still hearing how everyone enjoyed the comedian. The construction trade is not always east to amuse, but you hit it on the mark. We will surely pass along your info to our collegues.”
Janis H.
Chicago, IL
“Our team absolutely loved Tom Cotter! Not only did Tom put on a great show, but he was very generous with his time as well. A pleasure to work with. All in all, a wonderful experience.”

HOW BOOKING WORKS

We make hiring top entertainment simple with our easy 3-step process.

01
INQUIRE

Tell us about your event,
date, and your vision
for entertainment.

02
WE HANDLE
DETAILS

We work directly with the talent’s team to negotiate
and coordinate.

03
ENJOY YOUR
EVENT

Relax and enjoy as we
ensure a seamless,
memorable experience.

WHY CHOOSE HEADLINE ENTERTAINMENT

20+

Years of industry
experience.

600+

Professional
Entertainers.

5,000+

Successful Events.

500

Trusted by Fortune
Companies.

Celebrity Entertainment Booking Agent - Headline Entertainment

PREMIER BOOKING AGENCY FOR CELEBRITY TALENT

Your trusted source for America’s top corporate comedians, musical acts, and celebrity entertainment. Our philosophy is simple: deliver exceptional acts and expert guidance to make your corporate event, fundraiser, or private celebration unforgettable from start to finish.

Our discerning eye for talent, industry experience, and impeccable service sets us apart. Using long-standing entertainment industry relationships, we secure the right performers for your event at the right price. From affordable local headliners to world-famous celebrities, we ensure your next corporate meeting, gala, fundraiser, or special event becomes the success you need.

Ready to book your perfect entertainment? Contact us today for a personalized quote.