Ryan Gosling and Sean Penn's Biggest Disaster Is Now Streaming, Even If They'd Rather Forget It

13 Years Later, Ryan Gosling's Greatest Flop Is Now Streaming

Published Sep 27, 2026, 7:57 AM EDT

Erik Hawkins is an award-winning writer and editor who's been obsessed with cinema since he was old enough to hold Roger Ebert's Video Home Companion in his hands. He lives in NYC, where he rabidly watches everything from the newest releases to the more odd and obscure, and regularly shares his thoughts on Letterboxd. From ghost-writing fiction and webisodes in South America to local news, trial coverage, and politics in NYC, he's rarely put down his laptop over the past 15 years.

For decades, Hollywood has periodically chased the highs of the classic gangster picture, with Brian De Palma himself, years after his blockbuster hit The Untouchables, even trying with 2006's The Black Dahlia. Few of those films have fallen quite so hard on their faces, though, as Ruben Fleisher's expensive, star-studded attempt, Gangster Squad. Armed with a $60 million budget, a ludicrously stacked cast, and master cinematographer Dion Beebe, Fleisher somehow turned out a startlingly empty film that's jaw-dropping to watch today, 13 years after its release.

Ryan Gosling, Josh Brolin, and Emma Stone appear to be largely sleepwalking through the film — with Gosling appearing particularly sleepy — and the only potential bright spot, Sean Penn as an unhinged Mickey Cohen, isn't given much to do except occasionally shout from underneath pounds of Dick Tracy-style villain makeup. Gangster Squad did make some money at the box office, but was widely trashed and, today, could easily be considered the most disappointing film in both Penn and Gosling's filmography.

What Is 'Gangster Squad' About?

Set in 1949, Gangster Squad tells — in extremely historically loose fashion — the story of a small group of LAPD officers who fought against gangster Mickey Cohen and the blocs of elite Los Angeles society that helped him operate largely unimpeded for decades (the real Cohen was even reportedly friendly with Richard Nixon and evangelist Billy Graham). Brolin plays Sergeant John O'Mara, an almost comically straight and even "untouchable" detective who puts together a squad of similarly dedicated officers with the goal of disrupting Cohen's operations by any means necessary.

He's joined by Gosling, Giovanni Ribisi, Anthony Mackie, Michael Peña, Nick Nolte, and even Robert Patrick as they battle across the L.A. underworld and, in Gosling's case, fall in love with a similarly thinly-sketched femme fatale-cum-damsel in distress, played by Emma Stone. The plot largely follows the outline of The Untouchables to a T, despite being about an entirely different gangster and squad, with the group bonding, practicing shooting, losing members, almost losing hope, and, inevitably, proving victorious against Cohen (in an entirely fabricated encounter).

What Went Wrong With 'Gangster Squad'

To be honest, almost nothing goes right with Gangster Squad, and that issue starts with its director, Ruben Fleisher. Even if they're working from a dire script, a talented director with a sense of fun can bring something worth watching to the screen, as has been shown over decades of surprisingly fun and compelling DTV action films. However, Ruben Fleisher is a director whose best film is widely considered to be Zombieland, and here he is, trying to play De Palma with a script that was written as a barely coherent highlight reel of De Palma homages.

When the film was released, it was hit by some critics for "excessive violence," and while that may imply at least some pulpy, gory thrills on offer, Gangster Squad even disappoints in that department. Aside from a couple of brutal but obscured executions, the action scenes are rote, offering little spatial understanding or strategy but lots and lots of slow motion. It's possible the film suffered as well from reshoots following the Aurora, Colorado, movie theater mass shooting, but that wouldn't explain the lifelessness of virtually every scene before that redone shootout.

As noted above, every member of the cast is wasted. Penn at least offers energy, but he isn't given any fun lines to chew on, so his performance largely comes down to brooding and shouting. Gosling and Stone are intended as star-crossed lovers, but she's given nothing more to do than saunter slowly toward the camera in a red dress and warn Gosling about the wrath of Cohen. It's clichéd to an almost comical degree; as if a sketch writer were trying to do a quick send-up of every gangster picture ever made.

The story of the real Mickey Cohen is a fascinating and thorny one, packed with genuine brutality and hallucinatory meetings between the mob world and the "legitimate" one of business and politics. A straight, documentary retelling of that story would doubtlessly prove more engaging than the endless-feeling two hours of rote, childish cliché Fleisher offers here. It's the rare unqualified disaster for actors as gifted as Stone, Gosling, and Penn, and almost worth a watch as an instructional "what not to do" blockbuster.

Gangster Squad is streaming on Howdy.