Benjamin was born in New York City. He studied at The Actors Studio. He honed his craft in Off Broadway plays at the Joseph Papp's Public Theatre. His theatre work included "Short Eyes", "Cuba and his Teddy Bear", "The School of the America" and "The Resistible Rise of Arturo Ui". He received critical acclaim for performance in both his CBS and ABC Showcase. Benjamin moved to Los Angeles and garnered series regular roles in "Tru Calling", "Wanted" and "Moonlight', as well as recurring roles in "My Name is Earl", "Life", "Gemini" and most recently "True Detective: Season 2". Some of Benjamin's recent roles have included appearances in 'Castle" and "Ray Donovon". His favorite activities include, abstract painting, riding motorcycles, boxing and traveling.