He is known for playing Thomas Forrester on the CBS soap opera The Bold and the Beautiful and Brandon on Nickelodeon's Winx Club.

He graduated from Oak Hills High School in 2006, and was enrolled at Northern Kentucky University but dropped out to pursue his acting career.

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.