Santiago graduated in 2002 from F.H. LaGuardia High School for the Arts in New York City (known as the Fame school).
Raymond Santiago played Jorge Villalobos in the film Meet the Fockers, and had minor roles in 2005's Dirty Deeds and 2006's Accepted. He also starred as Michelle Rodriguez's brother, Tiny Guzman in the 2000 film Girlfight, as Lardo in 2009's Endless Bummer and as Alberto in Suburban Gothic.
He also played in the 2006 film The Sasquatch Dumpling Gang (also known as The Sasquatch Gang), alongside Justin Long, and in American Son along Nick Cannon. He also appeared in the 2011 film In Time. Santiago appeared in episodes of the television series My Name is Earl, Crossing Jordan, Law & Order: LA and Dexter. In the Ash vs. Evil Dead television series, he portrays Pablo Simon Bolivar, a Latino immigrant co-worker who becomes Ash's sidekick.
