Celebrity Entertainment Booking Agent - Headline Entertainment
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Gary Gulman

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BIOGRAPHy

Boston’s Gary Gulman has appeared on just about every television show a stand-up comedian can appear on including The Tonight Show, The Late Show with David Letterman, Stephen Colbert, Conan and the list goes on.  In 2016, he released his popular Netflix special, “It’s About Time.”  His brand of clever, original comedy has delighted audiences of all ages. While Gary has been a headlining comedian for several years now, he is well known for his breakthrough success on NBC’s Last Comic Standing as well. Over the past few years his charm and talent have also caught the attention of numerous television networks who have inked Gulman to star in lucrative comedy projects for them, including CBS, Showtime and FOX. Still relatively young, Gary’s work includes a Showtime Special, a critically lauded CD entitled Conversations With Inanimate Objects and the one hour DVD entitled Boyish Man. Gary also had a guest appearance on Inside Amy Schumer. Hi latest special is Gary Gulman: The Great Depresh (2019) on HBO right now! Comedy experts and fans praise Gary as one of the top comedians in the industry. He’s one of the most original artists out there.

Career Path

2003Broke through nationally as a standout finalist on NBC's 'Last Comic Standing', introducing Boston audiences to his cerebral, story-driven approach to stand-up.
2006Released the debut comedy album 'Boyish Man', capturing the sharp, character-rich voice that had made him a headliner on the club circuit.
2013Released 'Conversations with Inanimate Objects', a critically praised album that demonstrated the literary wit and precise language work that became his signature.
2016Dropped the Netflix special 'It's About Time', featuring his widely beloved riff on U.S. state abbreviations, which became one of the most-shared stand-up clips of the year.
2020'The Great Depresh' premiered on HBO, a landmark stand-up hour that broke open the conversation about mental health and depression with unflinching honesty and genuine comedy craft.
2023Published the memoir 'Misfit: Growing Up Awkward in the '80s', tracing his life from kindergarten through twelfth grade; Amy Schumer called it 'laugh out loud funny and heartfelt'.
2024The Max Original special 'Born on 3rd Base', executive produced alongside Conan O'Brien, premiered on the streaming platform, earning strong reviews for its introspective material about class and family.
2024Brought the 'Misfit Stand Up Tour' to performing arts centers and theater venues nationwide, translating the memoir's themes into all-new stand-up material.
2025Made his Off-Broadway debut with the solo show 'Grandiloquent' at the Lucille Lortel Theatre, directed by Tony Award winner Moritz von Stuelpnagel, for a sold-out run.

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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.”
Hank H.
Buford, GA
“Tom Cotter was absolutely outstanding from beginning to end. He was truly one of our best entertainers ever and class act as well. If you ever need a recommendation, I’d be honored any time to do that.”
Jeff L.
Bethel, CT
“The comedian you sent us for our corporate holiday party did a great job!! Extremely entertaining and funny. My staff is still laughing! If you don’t use Headline Entertainment again for your next event, you are making a mistake!”
TLPA
Las Vegas, NV
“Dan Naturman was a hit! We had one of our most entertaining banquets in years. Not only was his material very good, he was also able to interact off-the-cuff with the audience which really hit home with our group. Thanks for always responding quickly and ensuring the details were properly communicated.”
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.”
New York State Community Action Assoc.
Albany, NY
“You were a key part in the success of our conference. Thank you very much for a job well done. We look forward to working with you again!”
Rich G.
San Diego, CA
“Many thanks again or your part in making the event memorable for our customers.”
Chere C.
Lake Worth, FL
“Thank you so much for recommending Don Felder for ou fund-raising event. He and his band put on a fabulous concert! Our guests filled the dance floor and sang along to all the Eagles’ hits he performed. We could not have been happier!”
Steven K.
Bronx, NY
“I can’t tell you how much I appreciate you sending Johnny Lampert to our company holiday party. Beyond his material, I am still blown how he so smoothly took control of the room and came up with great stuff on the fly. Rave reviews from everyone.”
Katie H.
San Diego, CA
“Tom Cotter was wonderful. I do not think we could possible top him for next year!”
Lakewood Country Club
Rockville, MD
“On behalf of our membership and the management team I would like to thank you for the great show last Friday. We appreciate the extra time the headliner spent on his portion of the performance – realizing that the crowd was very much with him and enjoying the shtick. We are in the process of putting next year’s calendar together and we will be reaching out to secure your talents.”
Michael K.
St. Louis, MO
“You were right! Howie Mandel ls one quick-witted comedian, a total pro and easy to work with! The audience roared for almost an hour. I was amazed how quickly he won them over.”

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01
INQUIRE

Tell us about your event,
date, and your vision
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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+

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Entertainers.

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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.

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