Denisof was born in Salisbury, Maryland, the son of Christiana Taylor and Gerald Denisof. He is of Russian, Russian-Jewish, French, and Irish ancestry. He moved to Seattle, Washington, when he was three years old. He attended Highline College, where his mother was head of the drama department. After graduating from St. Paul's School in Concord, New Hampshire, he moved to London, England, at age 17, where he lived and worked for several years. While there, he studied at the London Academy of Music and Dramatic Art.
Beginning his career in the film industry, Denisof was the fight director for a stage production of Hamlet, and in 1991 was the fight director for the BBC's The Other Side, Romeo and Juliet, and The Soul's Dark Night. His first lead role was alongside Sir Christopher Lee in the feature film Murder Story (1989) where he played an investigative reporter. One of his first known works in television was on the arcade version of the video for "Got My Mind Set On You" by George Harrison. In 1995, he landed a small part in the 1995 movie First Knight, appearing as one of Arthur's round table knights in multiple scenes with Sean Connery and Richard Gere. Following those roles, Denisof worked with Sean Bean in three episodes of Sharpe as Lord John Rossendale in 1997.
His best-known character, Wesley Wyndam-Pryce, was first introduced in 1999 in season 3 of Buffy the Vampire Slayer as Buffy's replacement Watcher. Originally, Wyndam-Pryce was supposed to be killed off in the season 3 finale but, due to Whedon's surprise at how well he fit into the series, Denisof was given the choice about his character's fate and chose for him to live. As a result, Wyndam-Pryce later arrived as a motorcycle riding rogue slayer in season one, episode 10 of Angel, and was an official main cast member from episode 11 on, effectively replacing the late character Doyle. Wyndam-Pryce appeared in 100 out of the 110 episodes of the series.[citation needed]

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