Powers Boothe, star of such films as Tombstone, Sin City, and The Avengers as well as the television shows 24, Deadwood, and Marvel’s Agents of SHIELD has passed away. He passed away due to natural causes according to The Hollywood Reporter. He was 68.

If ever there was an actor born to play the mustache twirling villain in a story, it was Powers Boothe. I first came across his work in the movie Tombstone where he played Curly Bill Brocius, leader of the infamous gang The Cowboys. With all the talent in that movie, the fact that he stole the show playing the one character you wanted to see get what was coming to him spoke volumes of his ability as an actor. Speaking with American Profile in an interview talking about his role on the show Nashville, he talked of his love of playing bad guys

 â€œBut the heavies are more fun,” says the actor, 64, with a laugh. “And I think they’re more interesting.”

Powers also played the role of Gideon Malick in the Marvel Cinematic Universe. Debuting in The Avengers as a member of the World Council, his character would later appear in Agents of SHIELD as a member of the evil HYDRA organization. His appearance on Agents of SHIELD for this viewer gave his short role in The Avengers more malice in hindsight. It made you question the intentions of everyone on the World Council.

As always, when an actor of the stature of Powers Boothe passes on, you honor their work by rewatching the roles that made them famous. Whether it be his roles in movies or television, fire up the wayback machine and enjoy the legacy of a great villainous character actor. Powers Boothe will be missed.