Celebrity Entertainment Booking Agent - Headline Entertainment
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Billy Ray Cyrus

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BIOGRAPHy

Billy Ray Cyrus grew up surrounded by gospel music. Cyrus went on to fame as the multi-platinum hunky heartthrob behind such country hits as “Achy Breaky Heart,” “Could’ve Been Me,” “In the Heart of a Woman” and “Busy Man.” In March 2001, Cyrus hit TV screens in the role of a country doctor moved to Manhattan in the sitcom Doc. He returned to music world with 2003’s Time Flies and the gospel-inspired The Other Side, and in 2006, the same year Cyrus appeared on the Disney Channel’s Hannah Montana, a show starring his real-life daughter Miley, Wanna Be Your Joe came out and went gold. Riding on the wave of Hannah Montana’s popularity, Cyrus released his tenth studio album, Home at Last, in 2007. The album debuted at number 20 on the U.S. Billboard charts, both re-establishing Cyrus as a presence in country music and highlighting the popularity (not to mention influence) of his daughter’s show. More recently, Cyrus released Thin Line in 2016. Cyrus is still touring and breaking hearts wherever he plays.

Career Path

1992Released his debut album "Some Gave All," featuring the inescapable cultural phenomenon "Achy Breaky Heart."
2006Began co-starring in the Disney Channel hit series "Hannah Montana" alongside his daughter Miley Cyrus.
2019Featured on the massive record-breaking remix of Lil Nas X's "Old Town Road," winning two Grammy Awards.
2021Released custom collaborations focusing heavily on mixing traditional country with modern rap influences.
2022Gained attention for his engagement and subsequent marriage to singer Firerose, releasing music with her.
2023Continued to release independent EPs tapping into his folk and Appalachian musical roots.
2024Filing for divorce from Firerose amidst public speculation and heavily focusing strictly on family.
2025Scheduled to release a quiet, acoustic studio album re-recording his 90s country hits.
2026Planning a nostalgic acoustic-only storytelling tour across small theaters in the deep South.
2026Expected to release a comprehensive memoir detailing his massive highs and heavily publicized career shifts.

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WHAT OUR CLIENTS SAY

Sinai Free Synagogue
Mt. Vernon, NY
“Thanks so much for a terrific show at our synagogue last weekend. Everyone thoroughly enjoyed it and there’s already talk about planning our next show with you. There had been some skeptics who thought a comedy night wouldn’t work at our temple, but your great acts won them all over. Thanks again. We’ll be in touch to plan our next Sinai Free Synagogue Comedy Night.”
Monika E.
Westlake Village, CA
“Thank you for getting us Chicago for our gala. They were great to work with. I totally recommend this band… Great show! And they really work the audience. It’s nice that there are still original members too.”
Lisa B.
New York, NY
“The show was AWESOME. 10’s across the board. The comedians had people in tears! I would definitely use Headline Entertainment again for any occasion hands down!”
Valarie W.
Houston, TX
“I’d like to express my appreciation for Eric Dittelman’s performance for our United Way luncheon. He was a true professional. Employees are still commenting on how funny and amazing he was. I will definitely be referring him to others.”
Emmie L.
Washington, DC
“Eric Dittelman was wonderful! The audience really loved him and his performance really made the whole event”
Stacy B.
Trevose, PA
“I just wanted to thank you for the comedian you sent to our corporate meeting. Everyone was raving about him! My VP even said that in the 12 years we have been doing this event, he’s the best comedian we ever had. Thanks again!”
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.”
Bill A.
Houston, TX
“Thank you for securing Jeff Foxworthy for last night’s Gala. He was incredible and did a fantastic job with his routine and finished with a memorable testimony that tied in nicely with our mission and values.”
Amy C.
Gladstone, NJ
“Just a thank you for the great comedy night you provided the golf club with last evening. I received several messages from members this morning that said they laughed their heads off. Many thanks to you for the great recommendations.”
Sarah Z.
New York, NY
“The evening went great! I received so many compliments on The Mahoney Brothers. No only were they a pleasure to deal with – they were great performers and fun! You totally led us in the right direction. We shall work together again!”
Sarah L.
Topeka, KS
“Playing crazy catch up after a very successful event. All-American Rejects were awesome & our team absolutely loved it. Thanks for all your help.”
Congregation Beth Israel
Short Hills, NJ
“Thank you so much for hosting such a wonderful Zoom event for Congregation. We had over 100 family units sign up for this event. The comedians were funny, respectful and had us laughing all night long. We felt like we were sitting in a comedy club, not watching on a computer screen. We look forward to hosting another event with Headline Entertainment in the future!”

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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

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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.

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