Actor Powers Boothe, known for Deadwood, Agents of SHIELD, and Sin City, died on Sunday, May 14, 2017. His publicist, Karen Samfilippo, announced that he passed away of natural causes while asleep in his Los Angeles home. He was 68 years old.

Boothe had a reputation for the villain roles and for appearing in Westerns. Born on June 1, 1948 in Snyder, TX, he graduated from Southwest Texas State University then joined the repertory company of the Oregon Shakespeare Festival. In 1974 he made his New York debut in the Lincoln Center production of Richard III.

His film and TV debut came in ’77 in The Goodbye Girl. His film roles included Cruising, Southern Comfort, Red Dawn, Rapid Fire, Tombstone, Con Air, Men of Honor, MacGruber, Senator Roark in Sin City and Sin City: A Dame to Kill For, and The Avengers.

Throughout his career, Boothe appeared in several episodes to full arcs on a variety of TV shows. He was in Skag, Philip Marlowe, Private Eye, voiced Gorilla Grodd in Justice League and Justice League Unlimited, played the key role of saloon owner Cy Tolliver in Deadwood, was the vice president on 24, appeared in Nashville, and played Gideon Malick in Agents of SHIELD.