From 'Tombstone' to 'Nashville' : the Late Powers Boothe's Most Villainous Roles

Fallen Film Villain

Actor Powers Boothe, best known for his roles in the television shows Deadwood and Agents of S.H.I.E.L.D., as well as films like Tombstone, Sin City and The Avengers, died in his sleep from apparent natural causes on Sunday, his rep confirmed to PEOPLE. He was 68.

The actor was known for his effortless and convincing portrayal of baddies or "heavies," as he called them. "The heavies are more fun," Boothe told American Profile magazine in 2014.

Here's a look back at some of his best, baddest roles.

Cult Leader Jim Jones

Boothe's breakthrough role was in the 1980 CBS docudrama Guyana Tragedy: The Story of Jim Jones. The actor starred as demagogue and cult leader Jim Jones, a preacher who led 980 of his followers to commit mass suicide. The movie was released just two years after the real life incident, and earned Boothe an Emmy for his portrayal, which used dialogue from real tapes recorded by Jones as he instructed his followers to consume poisoned fruit punch.

Sinning Senator Ethan Roark

In 2005's Sin City, Boothe shined as the film's chief villain -- corrupt politician Senator Ethan Roark. The shady Senator was one of Boothe's most vile, R-rated characters -- Roark's dirty deeds included beating his wife to death with a baseball bat and continuously covering up for his rapist son.

Grinning Sociopath 'Curly Bill'

With his cunning portrayal of nefarious outlaw "Curly Bill" Brocius in 1993's Tombstone, Boothe stood out among a cast stacked with A-list actors like Kurt Russell, Val Kilmer, Bill Paxton and Sam Elliott.

Kilmer, aka Doc Holliday, paid tribute to the actor after his death on Twitter: "God bless Powers Boothe. Our very own Curly Bill from Tombstone. A true original."

Rogue Agent Joshua Foss

In 1995's Sudden Death, the actor squared off against legendary action hero Jean-Claude Van Damme as former CIA agent-turned terrorist Joshua Foss. Boothe's scene-stealing rogue agent takes the vice president hostage during the Stanely Cup Finals.

Marvel Baddie Gideon Malick

The actor appeared in The Avengers and in Marvel's Agents of S.H.I.E.L.D. as Gideon Malick, the duplicitous World Security Council leader who was evenutally revealed to be the leader of the terrorist-friendly criminal organization Hydra.

Dazzling Officer Vince Johnson

Though not a 100% villain, Boothe played Jessica Lange's lover in Blue Sky as she grows estranged from her husband played by Tommy Lee Jones.

Bad Dad Lamar Wyatt

In Nashville, Boothe played Rayna James' (Connie Britton) smooth-talking, manipulative father, Lamar Wyatt --- aka the reason behind James's (and her sister's) daddy issues.