He started out doing theater and studied at the Lee Strasberg Theatre and Film Institute in New York, with George Loros, Geoffrey Horne and Robert Castle.

He has guest starred in such series as CSI: Crime Scene Investigation, Medium, Boston Legal, ER and the season two premiere of Lie to Me.

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.

In an episode of The Walking Dead titled "Nebraska", Raymond-James played a young man named Dave, who presents a threat to series protagonist Rick Grimes and his group.

[4][5][6] In 2020, Raymond-James was cast to play the lead role of Gavin Wolcott in the NBC apocalyptic drama pilot La Brea which was written by David Appelbaum; [7] however, he left the project and was replaced by Eoin Macken.