Celebrity Entertainment Booking Agent - Headline Entertainment
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Chris Stapleton

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BIOGRAPHy

American singer-songwriter and guitarist, Chris Stapleton is one of the hottest acts on the music scene with six country number-one songs, including the five-week number-one, “Never Wanted Nothing More,” recorded by Kenny Chesney, “Love’s Gonna Make It Alright,” recorded by George Strait, and “Come Back Song,” recorded by Darius Rucker. Over 150 of Stapleton’s songs have appeared on albums by such artists as Adele, Luke Bryan, Tim McGraw, Brad Paisley and Dierks Bentley. Among other artists, he has co-written with Vince Gill, Peter Frampton and Sheryl Crow. After serving as the frontman of bluegrass group The SteelDrivers from 2008 to 2010, Stapleton released his debut studio album, Traveller, in 2015, which reached number one on the US Billboard 200 and was certified double platinum. Among several accolades, he won the Grammy Award for Best Country Album and Best Country Solo Performance at the 58th annual ceremony. His second studio album, From A Room: Volume 1, was released on May 5, 2017. Don’t miss the chance to see this great performer in action!

Career Path

1996Moved to Nashville to pursue a music career.
2007Co-founded the bluegrass band The SteelDrivers.
2010Formed the rock band The Jompson Brothers.
2015Released his debut solo album, 'Traveller'.
2015Won three CMA Awards, including Album of the Year for 'Traveller'.
2016Won two Grammy Awards for 'Traveller'.
2019Honored with the ACM Award for Songwriter of the Decade.
2020Released the album 'Starting Over'.
2023Released his fifth studio album, 'Higher'.
2025Won Best Country Solo Performance at the 67th Grammy Awards.

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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).

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WHAT OUR CLIENTS SAY

Hunterdon County YMCA
Annandale, NJ
“Just wanted to follow up and tell you that I’ve heard nothing but excellent comments from people in the community about the comedy show we had at our YMCA. Thanks for a great night!!! I would be happy to give you a great reference whenever you may need one.”
Meg J.
Newton, MA
“Thanks for adding such a wonderful dynamic to our Leukemia Comedy Night Fundraiser. You provided 300+ guests with the world’s best medicine – laughter. From a business standpoint, you were a pleasure too; responsive, professional and accommodating.”
Jeff T.
Dumas, TX
“Thanks for a great show with Sammy Kershaw. Crowd was into it and I don’t think I have ever seen the dance floor busier!”
Jewish Federation
Tucson, AZ
“Dan Naturman performed at our annual Men’s Night Out fundraising event and was an absolute genius. We had people there ranging in age from 12 years to almost 90 and everyone had a blast. This was one of our most successful events! Thanks Dan!”
Kathy D.
Toronto, CA
“I wanted to convey our deepest appreciation for the outstanding entertainment Tom Cotter performed and just as important, gratitude for the professionalism Tom displayed from his first communication to us until his standing ovation. Tom is clearly in a class of his own!”
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!”
Michelle S.
Nashua, NH
“The comedians were VERY weill received. I will certainly keep you in mind should we decide to hold another comedy night at our golf club. Thank you for your help.”
Emmie L.
Washington, DC
“Eric Dittelman was wonderful! The audience really loved him and his performance really made the whole event”
Kathleen M.
Newton, CT
“GREAT job putting together last night’s PTO comedy night at our Middle School. Your guys were hilarious!”
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.”
James T.
Washington, DC
“Tom Cotter was a pleasure to work with. Not only did Tom entertain an extremely tough and difficult audience but he went above and beyond to make sure his material was appropriate for our incoming Chairman’s young children.We can’t thank you enough and would recommend him highly!”
JCC Rockland
West Nyack, NY
“The comedians were terrific and great people to work with to boot! Just wanted to thank you on behalf of all of us at The J.”

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.