From Seven Psychopaths to Wild Horse Nine: Tracing Sam Rockwell's 20-Year Obsession with Playing Broken Men

Published Nov 8, 2026, 6:15 PM EST Ben Brewster is a filmmaker, critic, screenwriter, and actor whose work sits at the intersection of film culture, craft analysis, and storytelling. He is a movie list contributing writer at Collider and a contributing writer for High on Films, where he covers contemporary cinema, independent film, and festival releases with an eye toward narrative structure, performance, and visual language. Ben is an active film festival participant, having worked with Newport Film, the Nantucket Film Festival and as a screener for the Austin, Boston & Woodstock film festivals. He brings to that work a programming instinct shaped by years of close engagement with independent and documentary cinema. This comes with a deep investment in the kinds of films that rarely find their way into the mainstream conversation without someone willing to advocate for them. His background spans documentary and narrative filmmaking, film marketing, and production, including work with award-winning directors. This as well as developing his own indie production company, Lilac Creative Studio, through which he develops and produces original work across fiction and nonfiction forms. His debut documentary, Diamond in the Rust, is an examination of economic redevelopment and displacement in the Queens area of New York City. The film was recently accepted to the Unisphere Film Festival, the Defense of Democracy Film Festival, and the Urbanite Arts & Film Festival. This would mark his first festival recognition as a director. In addition to his writing and programming work, Ben hosts Beneath the Bloom, a film podcast exploring the work behind the scenes in cinema, and the struggles one can face to make a movie become a reality. The show reflects the same sensibility that runs through all of his work. A conviction that film is not merely entertainment but one of the most powerful tools human beings have for understanding each other. Across mediums, his work is driven by a deep belief in film as a communal, transformative art form. Sam Rockwell has spent the better part of two decades building one of the strangest filmography's in Hollywood, and this Fall he doubles down on that reputation with two of his most anticipated projects yet. He has a much-awaited reunion this Friday in theaters nationwide with Martin McDonagh (Banshees of Inisherin) for Wild Horse Nine, a dark comedy spy thriller that looks to promise that same chaotic energy McDonagh has pulled out of him before. He also voices the world-weary detective at the center of Brad Bird's animated neo-noir passion project Ray Gunn coming in December. Both roles fit a pattern Rockwell has followed since long before he signed onto either project, gravitating toward shattered men, hollowed out or quietly falling apart even when the surrounding film is a blockbuster or an animated feature aimed at a broad audience. Rockwell stands out from other actors of his generation for his refusal to chase conventional leading man material. He has never seemed particularly interested in being the hero in any traditional sense, opting instead to play cowards, has-beens, addicts and men undone by their worst impulses. He finds real humanity and even comedy inside characters who could have easily been played as pure caricature. But it is that instinct that has made him one of the most reliably interesting actors working today, someone directors write specific off-kilter roles for because they know exactly what he will bring to them. This piece traces that twenty-year obsession with broken men across nine defining performances. They range from supporting turns that captured the eyes of the audience to leading roles that redefined what audiences expected from him. Taken all together, they explain how Ray Gunn and Wild Horse Nine feel less like new directions and more like the next chapter in a career built entirely on embracing damaged figures. 9 'Good Luck, Have Fun, Don't Die' (2025) Image via Briarcliff Entertainment Sam Rockwell bursts into a Los Angeles diner in a clear plastic poncho covered in wires and tells everyone he is from a ruined future. Gore Verbinski directs the opening with the energy of a filmmaker returning after a decade away, and Rockwell matches him beat for beat. He threatens to set a bomb off unless the phone-obsessed regulars listen, and then promptly launches into a speech intended to recruit them to stop an AI apocalypse. Matthew Robinson's script loops that pitch so many times that the desperation of The Man From the Future becomes the core of the story. Rockwell plays him as a man who has failed and failed again but cannot stop trying. Reviews were split, with some calling it scattershot and others referring to it as a quirky anti-AI delight, though several singled out Rockwell as its best asset. Haley Lu Richardson, Michael Peña, Zazie Beetz, and Juno Temple lead the supporting cast alongside Rockwell's jittery charm. The Man From the Future, however, is a bit more mission than man, and the screenplay could have explored his grief in more depth. His desperation still gives Good Luck, Have Fun, Don't Die a passionate heartbeat. 8 'Ironman 2' (2010) Image via Marvel Studios Justin Hammer is the rare Marvel villain who is more pathetic than truly threatening or menacing, and of course Rockwell leans as hard as he possibly can into that notion. Jon Favreau's sequel to the famous 2008 original that kicked off the MCU saga casts him as a rival weapons contractor who wants Tony Stark's technology, fame and respect while having zero of his charm or charisma. Favreau mostly uses him for comic relief. His suits are sharp, his hair is perfect, and his insecurity exudes from his every step. Rockwell had reportedly tested for Stark, so playing the man who envies his every move carries a pleasing irony. His best scenes come when he realizes Mikey Rourke's Vanko is smarter than he is. Hammer springs him from prison and puts him to work on his armored drones, and discovers far too late that Vanko is working on his own agenda. Iron Man 2 sits low in most Marvel rankings (and with good reason) but Hammer remains one of its more colorful aspects even if the character is more of a sketch than a full portrait. 7 'The Bad Guys' (2022) Image via Dreamworks Rockwell voices Mr. Wolf in Dreamworks' The Bad Guys, the smooth-talking leader of a crew of animal criminals whose plan to fake a good deed spirals into its own mess. The crew consists of Marc Maron's Mr. Snake, Awkwafina's Ms. Tarantula, Craig Robinson's Mr. Shark, and Anthony Ramos's Mr. Piranha. Pierre Perifel directed the adaptation of Aaron Blabey's books, and its slick heist style gives Wolf plenty of room to show off his slippery morality. Wolf has been told his whole life that he is a villain, and the story focuses on the conception of him giving up that identity. It features a stylish heist look amongst jazzy music and sharp angles. Rockwell's voice carries a smirk and a hint of hurt in the same line. The 2025 sequel brought him back, which should say plenty about how well the lost wolf fits the actor's complicated persona. The performance proves that Rockwell's gift for wounded, flawed men translates to animation. Mr. Wolf and the crew land at 7 since it is a family comedy, which keeps his brokenness on the lighter side. 6 'See How They Run' (2022) Image Via Searchlight Pictures Tom George's See How They Run is a 1953 London murder mystery that pokes fun at Agatha Christie. The movie opens with Adrien Brody's Hollywood director narrating a mystery that reveals itself to be his own murder. Rockwell plays Inspector Stoppard, a weary and rumpled detective who drinks too much. Marck Chappell's script gives Rockwell dry one-liners and long stares into the middle distance. He is opposite the case with Saorise Ronan's Constable Stalker, and they make for a fun yet odd pairing. Rockwell's gift here is deadpan. He drags himself through interviews with a sleepy cynicism which acts against Stalker's bright-eyed and diligent note-taking. David Oyelowo, Ruth Wilson and Harris Dickinson round out a lively pool of suspects. Stoppard's sadness appears in glimpses, which suits Rockwell's talent for finding pain inside a joke. This is likely Rockwell's most relaxed performance on this list, and the movie works well as a fun diversion from the whodunit tropes. 5 'Three Billboards Outside Ebbing Missouri' (2017) Image via Fox Searchlight Pictures Martin McDonagh's Three Billboard's Outside Ebbing, Missouri earned Rockwell the Oscar for Best Supporting Actor, along with the Golden Globe, the BAFTA, and the SAG Award. That's a run almost no other supporting performance could match. Officer Jason Dixon begins the film as a bigot with a badge and ends as something much harder to put your finger on. Dixon is a violent man who lives with his mother and idolizes his chief, Woody Harrelson's Willoughby. Dixon attacks Red Welby, the advertising man who rented billboards to Frances McDormand's Mildred Hayes, by throwing him out of a window. Dixon's arc divides viewers, since some see real redemption and others see a character forgiven far too easily. However, Willoughby's letter, read after his death, is the turning point. Rockwell plays the scene with a fierce emotional depth that shows the ugly elements of all of his sadness and hurt. Rockwell finds the wounded child inside the bully, and McDonagh lets that discomfort stand. Fifth place says more about the layered performances encompassing this one and the overall depth of the list than any flaws in Rockwell's Dixon. 4 'The Green Mile' (1999) Image via Warner Bros. Pictures Frank Darabont's The Green Mile is the earliest entry here. Rockwell makes a big impression in a small amount of screen time as "Wild Bill" Wharton, a volatile inmate on a Louisiana death row in the 1930s. Based on Stephen King's serial novel, Michael Clarke Duncan's John Coffey and Tom Hanks's Paul Edgecomb get the emotional beats, while Wild Bill gets all the chaos. Wild Bill arrives like a lit fuse, grinning at the guards and daring them to hit him. Rockwell, barely thirty at the time, plays him with a twitchy glee that makes the whole block feel unsafe. Wharton is pure menace, but Rockwell hints at damage underneath, a man who has made cruelty his only personality. That unpredictability he shows here is the quality later directors would prize. He torments the guards and threatens the prison as a stage. The Green Mile ended up netting four Oscar nominations, including Best Picture and Best Supporting Actor for Duncan. Fourth place reflects how it's an early flash of what Rockwell could do, with the award-winning prison movie spending more time on its other characters. 3 Jojo Rabbit (2019) Image via Fox Searchlight Taika Waititi plays an imaginary Hitler as a cartoon, and Rockwell plays a Nazi with a conscience. Jojo Rabbit sets a satire inside Nazi Germany, and Rockwell is Captain Klenzendorf, the disillusioned officer who runs a Hitler Youth camp. He wears a flamboyant uniform, drinks heavily, and treats the training sessions like a joke he is tired of telling. Roman Griffin Davis's Jojo looks up to him, and Klenzendorf's contempt for the war gives the boy a glimpse of the man behind the costume. Klenzendorf is a broken man in a Nazi uniform who knows the cause is lost and cannot say so. Alfie Allen's Finkel and Rockwell share a private rapport that hints at a life that they cannot live openly. Jojo Rabbit won the Oscar for Best Adapted Screenplay, and Rockwell's quiet moments are a big reason the comedic beats work. Rockwell keeps the performance light and then lets one act of dignity and sincerity land that is among the most affecting tonal shifts of his entire career. 2 Vice (2018) Annapurna Pictures Amy Adams as Lynne Cheney and Steve Carell as Donald Rumsfeld give the political comedy Vice a bite, but Rockwell's Bush gives it a face. Bush is broken in a different way, because his brokenness is inheritance, a son living in a powerful father's shadow. Christian Bale vanishes into Dick Cheney in Vice, and Rockwell plays something far smaller, albeit stranger, as George W. Bush. His Busch is genial, unfocused and quietly desperate to prove he belongs in his father's world. Adam McKay's satire landed Rockwell a second consecutive Oscar nomination and McKay frames Busch as a boy who never outgrew his childhood. Rockwell makes you laugh at him and feel a small pang for him in the same moment. Rockwell's contrast with Bale makes Vice's central power imbalance a funny and disturbing microcosm of the larger thematic messaging. 1 'Seven Psychopaths' (2012) Image via CBS Films Seven Psychopaths arrived in 2012, and Rockwell's Billy Bickle is the fastest, funniest and most dangerous version of his persona. Billy is a would-be actor who steals dogs with Christopher Walken's gentle Hans. He pesters Colin Farrell's blocked screenwriter Marty with ideas for a movie. Marty's life tears open while Billy is trying to help him finish a script. Woody Harrelson's gangster Charlie wants his stolen Shih Tzu back, and Tom Waits shows up with a rabbit. Rockwell portrays Billy as a lonely man hiding underneath a false bravado, and as a person who needs drama the way most people need air. Seven Psychopaths gathers every thread of the broken men Rockwell had been playing since The Green Mile, and McDonagh gives him dialogue to match. Wild Horse Nine is their third film together, after Three Billboards. It follows two CIA agents, Rockwell's Lee and John Malkovich's Chris, sent from Santiago to Easter Island shortly before the 1973 Chilean coup. Walken, who co-starred in Seven Psychopaths, was originally attached to Wild Horse Nine before leaving the project. Early reviews have compared it to In Bruges, and Rockwell's Lee fits the tradition of McDonagh's wounded, wisecracking men. Seven Psychopaths lands at number one because it gave Rockwell the sharpest words and the largest amount of freedom. Release Date October 12, 2012