Riley was born and raised in Brooklyn, New York. His mother is from Trinidad and father is from Barbados. Riley attended Brooklyn Technical High School where he participated in the school's drama club. He went to college and received his B.A. in Theater from Lehigh University in Bethlehem, Pennsylvania in 2003. In 2006, he received his Masters in Theater from Ohio University. He played college football and wrote his first theatrical script which he also directed.
On Broadway, Riley played the role of Dave Robinson in Lombardi and starred in the 2009 production of Tennessee Williams Cat On A Hot Tin Roof as Brick, succeeding Terrence Howard in the role. In 2014, he appeared as Jay "The Sport" Jackson in the Old Globe Theatre's production of television Writer and Producer Marco Ramirez's The Royale. He also played Jared in the 2016 TV One movie Bad Dad Rehab.
From 2013 to 2016, Riley played Terrence Wall in the VH1 television drama series Hit The Floor.
In March 2017, Riley was cast in The CW's Dynasty reboot as chauffeur Michael Culhane.
