Powers Boothe, the Emmy Award-winning character actor known for playing villains, has died at the age of 68.

According to The Hollywood Reporter, Boothe passed away in his sleep on Sunday morning. His cause of death was believed to be of natural causes.

Few actors could emanate smugness and arrogance better than Boothe, leading to his casting in villainous roles across television and film. On the small screen, he appeared in Deadwood, 24, Agents of S.H.I.E.L.D., and Nashville. On the big screen, he was seen in Tombstone, Sin City, and Red Dawn.

In 1980, Boothe earned his only Emmy Award for his portrayal of cult leader Jim Jones in the mini-series Guyana Tragedy: The Story of Jim Jones. He twice received Screen Actors Guild nominations for his work in an ensemble; the first came in 1995 for Nixon and the second in 2007 for Deadwood.

Beau Bridges, a longtime friend of Boothe, was the first to announce news of his death: