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An Evening with Heather Headley

By Stephanie Woods-McKinney



The 92nd Street Y brings culture and enchantment uptown with the performance of iconic talent and Broadway star Heather Headley. Headley, a Trinidadian Grammy and Tony Award-winning artist, graced the stage to a sold out crowd . 92NY, is a cultural institution that embodies an impressive history of servicing the community with wellness, health & fitness, lifestyle classes and bringing diverse entertainment for all to enjoy. 


Headley is not your everyday R&B singer. The  accomplished artist is multifaceted jazz, gospel musician, record producer, and actress.


As the songstress strolled on stage as effortlessly as walking on clouds, the crowd of fans chanted and applauded. She opened with The Wizard of Oz classic “Over The Rainbow”, the timeless classic written by Edgar Yipsel Harburg and composer Harold Arlen. For the record, her version of the song was not your everyday chorus-Headley mesmerized the crowd with her transformation as she wore dazzling Cinderella shoes and flowing ensemble.


Headley, described the event as ‘songs from her wardrobe’ meaning she was presenting ‘layers of her being’. All of the musicians involved including her pianist Jason Webb were considered her ‘dressmaking’ tailors. Webb was named the seamstress which drew warm laughter from the crowd and she expressed the importance of the customized vision of the event. 

The positive tone for the afternoon was filled with heartfelt songs and melodies that touched the soul, she was witty, charming and took the audience down a long path of her impressive career which included her starring role in the critically acclaimed play “Aida” and gave her fans some insight regarding her close-knit family life, her music career and her bond with British pianist, songwriter, award-winning and worldwide best selling artist of all time Sir Elton John  


She described the moment John’s representative asked her to perform at his Kennedy Center Honors Award show where she sang “Your Song” her rendition of his classic track. Their relationship runs deep and she credits her role as Nala in the 1997 Broadway play “The Lion Kings" John personally asked her to star in the staged musical. 


All in all, Headley’s performance was an honor to witness.


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