Headline Jamaica

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Headline Jamaica For Artistes Bookings. Visit www.headlinejamaica.com or Email: [email protected] or Call 876 754 1526

Suite 15, Braemar Suites
1D Braemar Avenue
Kingston 10
Jamaica, W.I. Phone: (876) 754.1526
US Line: (305) 748.4602
Fax: (876) 906.3634

Today, we honour the courage, sacrifice and legacy of our national heroes. Happy Heroes Day 🇯🇲!
19/10/2026

Today, we honour the courage, sacrifice and legacy of our national heroes. Happy Heroes Day 🇯🇲!

Join us for Authentic: A Tribute to the Life of Allan “Skill” Cole, an evening of live performances, music and remembran...
16/10/2026

Join us for Authentic: A Tribute to the Life of Allan “Skill” Cole, an evening of live performances, music and remembrance in honour of a Jamaican icon.
📍 Ranny Williams Entertainment Centre
📅 Saturday, October 17, 2026
⏰ Performances begin at 9 PM
Featuring I-Wayne, Tjean, Warrior King, music by Rassarella, and special guest DJ Debz. Hosted by Tommy Cowan and Ali McNab.
Come out as we celebrate a legacy that continues to inspire.

Two powerhouse performers. One unforgettable celebration✨🔥.Headline Entertainment is proud to have Agent Sasco and Kevin...
08/10/2026

Two powerhouse performers. One unforgettable celebration✨🔥.

Headline Entertainment is proud to have Agent Sasco and Kevin Downswell joining the lineup for Diamonds Forever: Gospel & Reggae Fest on December 20.

Get ready for an unforgettable day of reggae, gospel and Jamaican music at the Diamond Hub Entertainment Complex.

01/10/2026

A special moment at Ras Ajai’s Setup. Sean Paul performing “Stand on Business,” with Tarrus Riley in the frame at Ranny Williams Entertainment Centre🔥.

01/10/2026

A night of reggae, dancehall and pure Jamaican energy🔥🇯🇲.
Spragga Benz,Sizzla Kalonji and I-Wayne in the building for the launch of Endeavors Reloaded.

Celebrating the life, work and legacy of a Jamaican musical icon. 🇯🇲Join the School of Sacrament Rastafari University fo...
30/09/2026

Celebrating the life, work and legacy of a Jamaican musical icon. 🇯🇲

Join the School of Sacrament Rastafari University for “Ibo Cooper: A Third World Hero”, a reflective conversation honouring the life and legacy of musician, educator, cultural advocate and founding member of Third World, Ibo Cooper.

📅 Sunday, October 11, 2026
⏰ 11:00 AM JA
💻 Join via Zoom - details are on the flyer.

A conversation on the legacy of a man whose work continues to shape Jamaica’s cultural and musical landscape.

Rest in peace, Lt Stitchie. 🕊️Stitchie holds a special place in my heart. I boarded my very first flight as a member of ...
29/09/2026

Rest in peace, Lt Stitchie. 🕊️

Stitchie holds a special place in my heart. I boarded my very first flight as a member of the entertainment fraternity with him, on a trip to the BVI. Mickey White managed him then, and I worked for Mickey. I will never forget that trip.
Long before that, Stitchie was my favourite artiste while I studied at the University of the West Indies. His energy, his humour and his lyrics carried me through those years. “Ambition” remains my favourite Stitchie song, and I will play it loud today in his honour.
Stitchie gave us laughter in the dancehall and hope in gospel. He fought hard these past two years, and he leaves a legacy that will live on.
To his wife Sophia, his family, his friends, his church family and his fans around the world, I offer my deepest condolences. We share your loss.
Tomorrow would have been his birthday. Walk good, Lieutenant.

— Jerome Hamilton, Headline Entertainment
HeadlineEntertainment

24/09/2026

A moment of praise, power and timeless Jamaican music🙏🏾✨

Flourgon takes the stage at the Excellence in Music Ceremony 2026 with a moving performance of “Glory Glory Hallelujah.” 🎶🇯🇲

A celebration of music, legacy and excellence.

Happy Birthday to the incredibly talented ALAINE ✨🎂Wishing you another year filled with love, light, beautiful music and...
21/09/2026

Happy Birthday to the incredibly talented ALAINE ✨🎂

Wishing you another year filled with love, light, beautiful music and countless moments worth celebrating. May this new chapter bring you continued growth, joy and inspiration.

Keep shining, Alaine💛🥂!

Legends in the house. Barrington Levy (centre) and Yellow Man (right) stopped by the Headline HQ at the same time. Big...
03/09/2026

Legends in the house. Barrington Levy (centre) and Yellow Man (right) stopped by the Headline HQ at the same time. Big up to Boss Man Jerome Hamilton in the mix.

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