Celebrity Entertainment Booking Agent - Headline Entertainment
Book Now!

Jelly Roll

Book Now!

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

Book Jelly Roll | Request A Quote

  • Important: To ensure our response to your inquiry, we ask that you please take a moment to read the following:

This site is designed for talent buyers interested in contracting artists for live performance at corporate, private functions and special events. Please be aware that all our contracts require pre-show secured financial commitments (binders and/or deposits).

We also regret that for legal and contractual reason we cannot respond to inquiries related to any of the following:

  • Requests for artist to play at non-paying fundraisers.
  • Requests to fwd. messages or for contact information.
  • Invitations to appear to accept awards, donate items for auctions, etc.
  • Requests for print, radio or TV interviews.
  • Upcoming public appearances of artist on the site.
  • Requests regarding TV or film projects.
  • Requests to forward jokes, songs, lyrics, etc.

In order for us to best understand your needs, we appreciate initial contact to be through the form below. If you prefer to speak with someone or your inquiry requires more immediate attention, please call us at 888.5526737.

Regular office hours are Monday–Friday, 10:00 AM – 7:00 PM (EST).

We typically respond within 24 hours

WHAT OUR CLIENTS SAY

Jennifer C.
Perth Amboy, NJ
“I want to thank you and your crew for a great show for our comedy night fundraiser! You guys were awesome!!! It was an absolute pleasure meeting you all!”
Mark F.
New York, NY
“Tom Cotter did an absolutely great job! The feedback from both nights has been outstanding!”
Sarah A
New York, NY
“They absolutely loved Eric Dittelman! They said he was a big hit. It was an absolute pleasure working with you and Eric! We will absolutely be recommending him to our clients for more events!”
Claire C.
Denver, CO
“You knocked it out of the park with Everclear for our private concert on such short notice. I told you what vibe, and genre I wanted and you presented me with a list of bands/artists to pick from and you did everything! The communication and service was nothing but top notch. I highly recommend Headline Entertainment for your next entertainment booking needs.”
Erma R.
Tampa, FL
“Dan Naturman was the headline entertainer at our Night at the Catskills and we could not have asked for a more perfect comedian! His material was fresh, clean, and intelligent.”
Suzanne S
Frankenmuth, MI
“Both Jeff Caldwell & Eric Dittelman were hits! We heard nothing but positive comments from people. As always, you’re a pleasure to work with. Thanks again for providing us with two quality entertainers!”
Corey H.
Palm Springs, CA
“We loved your show at our corporate meeting and sales conference in Palm Desert. It was a gut busting performance that I won’t soon forget. I literally thought the guy next to me had wet himself; he couldn’t catch his breath for 5 minutes!”
Cystic Fibrosis Foundation/CT Chapter
Wheathersfield, CT
“Thank you, thank you, thank you! We have had nothing but rave reviews from our guests about the comedians you sent us. The humor was witty, polished, and lively. Thank you for making my job entertaining, while also helping us raise over $15,000 to find a cure for cystic fibrosis!”
Small Ventures USA
Houston, TX
“The show last week with Natalie Merchant went great. It was a rousing success. Thanks for your help in booking her. Hopefully we will have a reason to work with you again for the next milestone!!”
Muscular Dystrophy Foundation
Dallas, TX
“Mentalist Oz Pearlman was terrific. ! Such a wonderful person and great act. We had a terrific time with him.”
Malachi L.
Jamestown, NY
“We couldn’t be happier with Tom Cotter’s involvement. His show was honestly the best out of the whole festival. I haven’t heard so much laughter from an audience before – kudos!”
Adrien G.
Berks County, PA
“Thank you for the terrific evening of comedy you provided for our fundraising event. The show was absolutely perfect. This was our first year doing a comedy night, but it was such a success that I already know we will be in touch for next year.”

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.