After No Country for Old Men, Josh Brolin started landing more prominent, and sometimes even leading roles in promising pictures. He nabbed a part in Ridley Scott’s American Gangster and then took on the task of portraying embattled outgoing President George W. Bush in Oliver Stone’s 2008 feature W. It was his turn as San Francisco politician-turned-assassin Dan White in Gun Van Sant’s biopic-drama Milk that earned Brolin his first (and, so far, only) Oscar nomination for best supporting actor.

He’d soon earn the title role in Jonah Hex; reunite with Tommy Lee Jones (well, sort of) as the younger version of his Agent K in Men in Black 3; and work with the Coens again for True Grit

Brolin has also had his fair share of letdowns, of course, including the ill-advised 2013 remake of Oldboy, the lackluster period crime-drama Gangster Squad, the little-seen and critically disfavored romantic drama Labor Day, and the too little, too late sequel to Sin City

That downturn proved short-lived, as Brolin found himself right back in the critical sweet spot with appearances in highly respected pictures such as Paul Thomas Anderson’s Inherent Vice, Denis Villeneuve’s Sicario, and the Coens’ Hail, Caesar! 

With that kind of filmography, it’s no wonder Brolin became a prime candidate for not one, but two superhero spots.

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