Raymond-James was born in Detroit, Michigan, and graduated Clarkston High School in 1996, where he was a football and track standout. He started out doing theater and studied at the Lee Strasberg Theatre and Film Institute in New York. Following several stage appearances in New York, including 'The Petrified Forest' at the Pantheon Theater, he relocated to Los Angeles.
He has guest starred in such series as CSI: Crime Scene Investigation, NCIS, Medium, Boston Legal, ER and the season two premiere of Lie to Me. He starred in the FX original series Terriers which was canceled by FX on December 6, 2010 after the first season.
In his feature debut Raymond-James played the best friend of Justin Timberlake's character in Black Snake Moan with Christina Ricci and Samuel Jackson.
He also starred in Once Upon a Time as Neal Cassidy/Baelfire.
- In Once Upon A Time, his character's girlfriend was portrayed by Sonequa Martin-Green.