Oprah was in The Bahamas supporting her good friend, Sir Sidney Poitier, while The Bahamas was honouring him to kick off their 40th anniversary celebrations. Rolle was commissioned to present a portrait of Poitier for that occasion when the Paradise Island bridge was renamed in Poitier’s honour.
“Throughout my professional career Oprah Winfrey has always been an inspiration to me, ever since I listened to her many orations on life and principles of success,” said Rolle. “During the organizing of the Sir Sidney Poitier bridge dedication, I was commissioned to commence a portrait for Oprah Winfrey who I had been in a pursuit to meet for years now.”
Rolle considers this piece to be one of his best works to date. A private dinner was organized where he presented it to her as a gift from the Bahamas government. Oprah was said to be immediately captivated by the portrait saying, “Wow, that is me. You got everything right. Wow, my eyes and everything.”
The artist said he was shocked to hear her reaction as she looked at the drawing with delight. Miss Winfrey took the time to chat with Rolle about the portrait, as she was interested in the mechanics of how he was able to draw her in such detail. “She took my contacts with her as she constantly praised me. It was a surreal experience and a blessing of notoriety that I will always cherish,” said Rolle.
