Rolle has received wide attention and critical acclaim for his depictions of U.S. President Barack Obama,[2] Prince Harry,[3][4] Sir Sidney Poitier,[5] Oprah Winfrey, Johnny Depp,[6] and Michael Jackson.
[7] Rolle is a multi-disciplinary artist, working in mediums including acrylic, oils, charcoal, graphite, colored pencil, pastels, digital media, and cosmetics and has embarked on creating artwork using food.
Rolle later transitioned to drawing live portraits and caricatures at the Marina Village, Atlantis Paradise Island in the Bahamas.
[6] Rolle is the artist and writer behind the socio-political news column, "Pushin Da Envelope", featured on weekdays in The Tribune newspaper in the Bahamas.
He displays this portrait at his studio in downtown Nassau and it has received heavy attention from the thousands of American tourists that pass by on a daily basis.