Gregory was born in Cincinnati, Ohio, the youngest of three sons. His brothers are Shannon, a pilot and Scott, who serves in the Navy. He graduated fromOak Hills High School in 2006, and was enrolled at Northern Kentucky University but dropped out to pursue his acting career. He is married since February 2010 to Sheridan Nicole, and their son, Kannon Gregory, was born on 8 January 2013. He appears as Ashley Tisdale's ex-boyfriend in her music video for "It's Alright, It's OK". Gregory played the role of Ty Collins in The CW's 90210, who takes interest in Shenae Grimes' character during the first season. In August 2010, he was cast as the new Thomas Forrester on CBS' daytime soap opera The Bold and the Beautiful, taking over the role from Drew Tyler Bell. He stayed with the show for three years but was written out in late 2013. He models for Nous Models and he is practicing in boxing.

• Saints and Soldiers: The Void (2014)

  
• What Would Jesus Do? (2010)

  
• The Veil (2017)