Celebrity Entertainment Booking Agent - Headline Entertainment
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Estelle

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BIOGRAPHy

She may be a born-and-raised West London girl, but we’d venture that Estelle Swaray is right at home in the energy of New York, her newly adopted city. Estelle debuted with Shine, which was without question one of 2008’s most compelling releases. Executive Produced by John Legend and Atlantic Records Chairman/CEO Craig Kallman, the album proved Estelle’s global breakthrough, fuelled in part by the phenomenal hit single, “American Boy (Feat. Kanye West).” In addition to hitting #1 in the UK, “American Boy” topped the European Airplay Chart, along with airplay charts in the UK, France, Italy, Belgium, Denmark, and Ireland. In the US, “American Boy” has been certified 2x-platinum by the RIAA for digital sales exceeding 2 million. And in 2009, the track earned Estelle her first-ever Grammy Award, among many other prestigious honors. In 2012, Estelle released All of Me. She continues to perform around the globe.

Career Path

2004Dropped debut album 'The 18th Day' on V2 Records in the UK, charting in the Top 40 with singles '1980' and 'Free' and announcing a West London voice built for both rap and soul.
2007Took home the Grammy Award for Best Rap/Sung Collaboration for 'American Boy,' which was also certified 2x-platinum by the RIAA for US digital sales exceeding two million.
2007Performed 'American Boy' live at Apple Music Studios for the new Apple Music series 'The One,' pairing cinematic visuals with an intimate reimagining of her signature global hit.
2008'Shine,' executive produced by John Legend and Atlantic Records Chairman Craig Kallman, delivered the global crossover hit 'American Boy (feat. Kanye West),' which reached #1 in the UK and topped European Airplay charts in France, Italy, Belgium, Denmark, and Ireland.
2012Followed 'Shine' with 'All of Me,' featuring the Grammy-nominated single 'Thank You' and expanding her audience across the US and UK.
2013Joined Cartoon Network's 'Steven Universe' as the speaking and singing voice of Garnet, a lead character whose depth and emotional arc made the casting one of the most praised in modern animated television.
2018Returned to her roots with 'Lovers Rock,' a reggae-soul album that drew glowing critical reviews and showcased range far beyond the club-ready sound of 'American Boy.'
2019Reprised Garnet for 'Steven Universe: The Movie' and the follow-up limited series 'Steven Universe Future,' cementing the character as a landmark representation in children's media.
2025Released 'Stay Alta,' her sixth studio album, featuring collaborators D-Nice, Joi, Teedra Moses, and Durand Bernarr across a predominantly uptempo set that reasserted her as a versatile, forward-moving artist.
2025Released the single 'Live, Love, Learn,' continuing the creative momentum of 'Stay Alta' and keeping her profile active with new material for international audiences.

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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

Birchwood Country Club
Westport, CT
“Thank you so much – rave reviews!! Headline Entertainment provided great entertainment for our annual golf night! This event kicks off the golf season and Johnny Lampert was the kicker – MVP in my book!”
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!”
Kathleen M.
Newton, CT
“GREAT job putting together last night’s PTO comedy night at our Middle School. Your guys were hilarious!”
Emily T.
Omaha, NE
“Our show with Herman’s Hermits starring Peter Noone went great!! Everyone loved it!!”
Muscular Dystrophy Foundation
Dallas, TX
“Mentalist Oz Pearlman was terrific. ! Such a wonderful person and great act. We had a terrific time with him.”
Congregation Chisuk Emunah
Harrisburg, PA
“What a great night! Thanks for being so funny and for staying within the boundaries. Everyone enjoyed. Hope you did too!”
Temple Kehilat Shalom
Gaithersburg, MD
“Folks are still raving about the show. Out of the six or seven Temple Comedy Nights we have had, yours was the best!”
Jen I.
Brookfield, CT
“Our PTO and guests had such a blast with our Comedy Night. Both acts were fantastic and we are still laughing 2 weeks later! You came through in every way! Our PTO is already talking about planning another comedy night, so I will be in touch.”
Daniel G.
North Brunswick, NJ
“On behalf of our entire congregation, I can’t thank you enough for the GREAT show you put together for our comedy night at our temple.. This was our 3rd comedy night and it was the best, thanks to you. We look forward to working with you again!”
Mark F.
New York, NY
“Tom Cotter did an absolutely great job! The feedback from both nights has been outstanding!”
Chris H.
Lakewood, MD
“Thank you for the great performances last Friday night at our country club’s comedy night. All three acts really put on a great show. We are putting next year’s calendar together and I will reach out to secure more of your talents for sure.”
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!”

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.