Top 10 Josh Brolin Flicks You Can’t Miss, Ranked

10. Gangster Squad

Kicking off our list with a bang, or rather, a Tommy gun spray, ‘Gangster Squad’ might not be high art, but Brolin’s no-nonsense performance is a solid reason to watch. The film received mixed reviews and grossed $105 million worldwide, which isn’t too shabby for a flick that was delayed due to real-world events. And let’s face it, Brolin in a fedora and a suit is worth the price of admission alone. Josh Brolin’s role in this fictionalized account of the LAPD’s battle against Mickey Cohen and his gang provides enough grit and gumption to make you almost forget the film’s historical liberties.

Top 10 Josh Brolin Flicks You Can’t Miss, Ranked

9. Inherent Vice

Diving into the psychedelic ‘Inherent Vice,’ Brolin’s portrayal of a straight-laced detective in a sea of hippies is as hilarious as it is unexpected. It’s his character’s peculiarities that build up throughout the film, making him the real attention-getter. Josh Brolin’s performance as Sportello’s sometimes-partner/sometimes-antagonist Lt. Detective ‘Bigfoot’ Bjornsen is the real attention-getter, and it’s not hard to see why. His comedic timing amidst the chaos of this trippy narrative is a testament to Brolin’s range as an actor.

Top 10 Josh Brolin Flicks You Can’t Miss, Ranked

8. Oldboy

Sure, ‘Oldboy’ is a divisive remake, but Brolin’s intense performance is worth the price of admission, even if the movie makes you want to lock yourself away for a while. While some may argue that the film didn’t quite capture the essence of the original, Brolin’s commitment to his role cannot be denied. His raw and gritty transformation into a man bent on revenge shows he isn’t afraid to tackle challenging material.

Top 10 Josh Brolin Flicks You Can’t Miss, Ranked

7. Men in Black 3

Time-traveling to save the world? All in a day’s work. Brolin’s uncanny Tommy Lee Jones impression in ‘Men in Black 3′ is so spot-on, it’s almost an alien conspiracy. He spent three months perfecting Jones’ mannerisms and voice, and it shows. Man, this is uncanny, people said, and they weren’t wrong. It’s performances like these that remind us that Brolin can do more than just play tough guys—he can also nail a comedic role.

Top 10 Josh Brolin Flicks You Can’t Miss, Ranked

6. Sicario

‘Sicario’ is a gritty, no-holds-barred look at the drug war, and Brolin’s morally ambiguous character will have you questioning everything, except his acting chops. With flip-flops and casual attire contrasting sharply with the suited men who report to him, his portrayal underlines an unconventional approach to his role. The conflict arising from his character’s actions adds depth to an already intense narrative.

Top 10 Josh Brolin Flicks You Can’t Miss, Ranked

5. True Grit

In ‘True Grit,’ Brolin hides behind a grizzled exterior, giving us a villain who’s easy to hate but hard not to admire for his sheer Brolin-ness. His portrayal added another layer to an already compelling remake led by Jeff Bridges. It’s these kinds of roles that prove Brolin can steal scenes without saying much—his presence alone speaks volumes.

Top 10 Josh Brolin Flicks You Can’t Miss, Ranked

4. Milk

In ‘Milk,’ Brolin goes against type as a troubled politician, delivering a performance so good it almost makes you forget he’s the villain. Almost. The complexity of his portrayal garnered critical acclaim and proved that he could hold his own against heavyweights like Sean Penn. This role showed audiences that there’s more to Brolin than just playing tough guys; he can also play deeply flawed human beings with nuance.

Top 10 Josh Brolin Flicks You Can’t Miss, Ranked

3. No Country for Old Men

In the Coen Brothers’ masterpiece, ‘No Country for Old Men,’ Brolin’s portrayal of Llewelyn Moss, a man on the run, is so compelling that you’ll be rooting for him despite everything—including his questionable haircut. His character may not have been cut out for the world of drug money and violence he stumbles into, but Brolin certainly was cut out for this role.

Top 10 Josh Brolin Flicks You Can’t Miss, Ranked

2. Avengers: Infinity War

In ‘Avengers: Infinity War,’ Brolin’s Thanos is not just any old villain; he’s a giant purple alien with surprisingly relatable motivations (if you squint). His nuanced performance made audiences feel for Thanos—a feat not easily achieved when your character’s goal is mass genocide. It’s this humanity-filled portrayal that elevated what could have been just another bad guy into an iconic figure within the Marvel Cinematic Universe.

Top 10 Josh Brolin Flicks You Can’t Miss, Ranked

1. Avengers: Endgame

Topping our list, ‘Avengers: Endgame’ cements Brolin’s legacy as Thanos, giving us a performance that’s not just universe-altering but also career-defining. It’s hard not to admire how he brought depth and gravitas to what could have been just another CGI-heavy role. As the beating heart of one of cinema’s most significant events, it’s no wonder this flick sits at number one—it’s where both Thanos and Brolin reached their pinnacle.

Top 10 Josh Brolin Flicks You Can’t Miss, Ranked

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