He was born in Kansas City, Missouri in 1952, to Holly and Jack Groo Massee. The family moved to Paris, where Massee grew up and, after high school, he came back to the United States settling in New York, where he graduated from Hunter College and studied acting at the Neighborhood Playhouse School of the Theatre.
In 1993, Massee portrayed the character Funboy in the film The Crow, starring Brandon Lee. Massee was the actor who fired the shot that killed Lee by accident on the set in 1993, due to an improperly prepared prop gun. He was so traumatized by the event that he returned to New York and took a year off from acting. He refused to view the film. In an interview in 2005, 12 years after the incident, Massee revealed that he still had nightmares about it, going on to say, "I don't think you ever get over something like that."
In 1995, Massee played the cop Newton in the film Tales from the Hood. He has provided the voice for the villain Spellbinder in The Batman, as well as appearing on the television series 24 as the villain Ira Gaines. He provided the voice of Bruce Banner for the Ultimate Avengers animated film, as well as the sequel Ultimate Avengers 2. He appeared in the film Seven alongside Brad Pitt and Morgan Freeman. He appeared in David Lynch's Lost Highway as Andy. He played the physical manifestation of Management (a.k.a. Lucius Belyakovin) on HBO's Carnivàle. He guest-starred in The X-Files episode "The Field Where I Died". He also appeared in the 2005 NBC TV miniseries Revelations as the main antagonist. In 2006, he guest-starred in Criminal Minds as a serial killer on death row. He also guest-starred in the Law & Order: Criminal Intent episode "Reunion" as a rock star. He appeared in the American TV series FlashForward as villain Dyson Frost. He appeared as a hunter, Kubrick, on the series Supernatural in 2007.
Massee married Ellen Sussdorf in 1997, with whom he has two children: Jack and Lily. The couple owned a clothing boutique in Los Angeles.
Massee portrayed imprisoned serial killer Charles Hoyt in the first two seasons of the TV series Rizzoli & Isles. He played the role of Gustav Fiers (alias The Gentleman) in 2012's The Amazing Spider-Man and reprised the role in the 2014 sequel The Amazing Spider-Man 2.
Massee died of stomach cancer in Los Angeles on October 20, 2016 at the age of 64.
