Powers Boothe, the character actor known for playing villainous roles in films like Sin City and Tombstone and television series like Deadwood and Agents of S.H.I.E.L.D., died Sunday morning at his home in Los Angeles. He was 68.

Boothe’s representative confirmed the actor’s death to The Hollywood Reporter, adding that Boothe died in his sleep from natural causes.

Actor Beau Bridges was the first to share news of Boothe’s death on Twitter. “It’s with great sadness that I mourn the passing of my friend Powers Boothe. A dear friend, great actor, devoted father & husband,” Bridges wrote.

Boothe was known for portraying rival brothel owner Cy Tolliver on three seasons of Deadwood, where he became the town nemesis to Ian McShane’s Al Swearengen. In recent years, the actor had a reoccurring role as tycoon Lamar Wyatt on the country music drama Nashville.

Born to a sharecropping family in a small town in Texas, Boothe was introduced to acting while performing in summer stock during his junior year at Texas State University. After a fellowship in the dramatic arts from Southern Methodist University and a brief tenure with the Oregon Shakespeare Company, Boothe moved to New York, where he landed a Broadway role in the play Lone Star in 1980.

That same year, Boothe starred as cult leader Jim Jones in the made-for-TV film Guyana Tragedy, a role that earned him an Emmy Award for best actor.

Although Boothe did have his share of roles where he wasn’t cast as the bad guy – like Philip Marlowe in the short-lived HBO series about the Raymond Chandler detective – the actor relished the more nefarious characters. “The heavies are more fun,” Boothe told American Profile in 2012. “And I think they’re more interesting.”

After first finding success for portraying the man responsible for over 900 deaths at Jonestown, Boothe largely spent the remainder of his career typecast as the villain in both movies and TV shows: As a terrorist in Sudden Death, a drug trafficker in Extreme Prejudice, Hydra agent Gideon Malick in the Marvel Cinematic Universe, scene-stealing outlaw Curly Bill Brocius in Tombstone, the manipulative Vice President Noah Daniels on 24 and warped patriarch Senator Roark in Robert Rodriguez’s Sin City.

“I loved working with Powers Boothe. A towering Texas gentleman and world class artist. Rest In Peace, amigo,” Rodriguez tweeted Sunday.

Boothe also played White House Chief of Staff Alexander Haig in Oliver Stone’s Nixon and Colonel Faith in the comedy MacGruber, directed by the Lonely Island’s Jorma Taccone.

“Powers Boothe was an unbelievably talented actor and sweet sweet man. He will be sorely missed. There will never be another Colonel Faith,” Taccone tweeted Sunday.

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