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According to his publicist, actor Powers Boothe died in his sleep last night in his Los Angeles home due to natural causes at the age of 68.

Boothe was known for his roles in Deadwood, Sin City, Tombstone, and, most recently in the Avengers movie and Agents of S.H.I.E.L.D. where he portrayed Gideon Malick, a key figure in Hydra who eventually turned on the organization. His iconic voice made him a favorite choice to play such villains, and even voiced Gorilla Grodd in the Justice League animated series.

Boothe is survived by his wife Pam, whom he’d been married to for 48 years and their two children Parisse and Preston.