Philip Seymour Hoffman’s 50 Greatest Roles

Blink and you’ll miss it (but perhaps the only reason we’re even still talking about this movie), Hoffman’s film debut in this ambitiously strange, black-and-white crime flick introduces us to him in all his character glory. Decked out in fingerless gloves, a sleeveless t-shirt, and that BANDANA, his skeezy pool-player goes by “Klutch” and spends all of his screen time laughing maniacally and acting douchey. It’s a brief scene, but fascinating to watch with the knowledge of where his career wound up going.

Where to Stream Triple Bogey on a Par Five Hole

This Alec Baldwin-led adaptation of The Getaway familiarly throws Hoffman into one of his trademark 90s, working class schlubs who meet a grisly fate. Despite the fact that he could have remained relegated to these kinds of roles for his entire career, he truly set himself apart from others doing the same thing by bringing a fresh charisma to an otherwise negligible character.

Where to Stream The Getaway

Basically a knock-off of Pulp Fiction, this bonkers flick does little else but gift us with Hoffman in another scuzzy character role. The flick is packed with an all-star cast, including Stanley Tucci, Robbie Coltrane, John Ritter, and more, but for the most part, it has no idea what to do with them. Due to the film’s general air of forgettability, Hoffman’s conniving money man Duncan turns into one of his most insignificant roles. (Despite all of this, however, it’s still hard to look away when he’s on screen. He’s just that captivating.)

Where to Stream Montana

As the ill-tempered early roommate of Robin Williams‘ zany protagonist, Hoffman unfortunately is given an uneven character arc that pushes an already-silly film into frustratingly twee territory. It’d be one thing if he was consistently villainous, but by the film’s final act, it feels as though the writer forgot what they were doing and just lazily put him in line with the rest of Adams’ admirers.

Where to Stream Patch Adams 

There is a lot going on in Flawless, and Hoffman is arguably the most redeeming part of the whole thing. Directed by Joel Schumacher, the flick follows a super conservative police officer (Robert De Niro) who suffers a stroke and gets assigned to a rehab program that involves singing lessons with the drag queen next door (Hoffman). The flick is rife with cliches, but Hoffman’s Rusty is soulful, melancholy, and absolutely compelling, even under all that makeup.

Where to Stream Flawless

As with many early Hoffman roles, his part in Leap of Faith may be small, but he makes it mighty. Featured among an ensemble cast led by Steve Martin, Hoffman plays one of the eccentric cronies who help Martin’s con-artist evangelist swindle people out of their assets for their own gain. While most of the dramedy falls short of expectations, Hoffman and his team manage to breathe life into an otherwise underwhelming flick.

Where to Stream Leap of Faith

Another early role that might have been inconsequential for any other actor proves to be a memorable one for Hoffman in this quirky comedy starring Diane Lane. As Chris, another on the list of crooked, big-talking small timers, Hoffman is nothing short of magnetic despite his limited screen time.

Where to Stream My New Gun 

Once again proving early on he could hold his own opposite A-listers like Michael Madsen, Benicio Del Toro, John Cusack, James Gandolfini, and more, Hoffman’s supporting role as a small-time crook a little better at his job than he lets on helps to slightly elevate a largely middling film.

Where to Stream Money for Nothing

Sure there’s twisters, Bill Paxton, and lots of tense scenes, but Hoffman’s goofy Dusty brights a lightness to Jan De Bont’s high-stakes nature film. It’s worth noting that this easily could have been the kind of character Hoffman played for his entire career (and lived comfortably because of it). We should be grateful that he went on to diversify his resume with the projects that followed, because even if Dusty’s goofy schlub was entertaining, what Hoffman later showed us he was capable of was just too good to pass up.

Where to Stream Twister

That mop of red hair and totally effortless charm despite his total privilege and deceptive innocence have been credited for helping Paul Thomas Anderson to fall in love with Hoffman. Even in a film led by screen god Al Pacino, Hoffman manages to steal the show in a relatively minor role, schmoozing it up with whoever to ensure that his life remains as easy as possible. While Chris O’Donnell may have been the intended young lead, it’s hard to pay attention to him when Hoffman’s up to his antics.

Where to Stream Scent of a Woman

Armed with an all-star cast and directed by Mad Men alum John Slattery, God’s Pocket is unabashedly festival fare, gritty and grimy as these flicks come. While the flick is mildly murky, Hoffman’s low-level criminal Mickey is as solid as protagonist as any when it comes to films with this DNA, and he easily delivers on the promise of his talent as Mickey begins to fear losing everything he’s worked for.

Where to Stream God's Pocket

It’s hard to plunge Hoffman into a role that carries the same wise leader charisma as his iconic Almost Famous part, and unfortunately, it mostly feels like Richard Curtis’ flick can’t really support Hoffman’s greatness. Pirate Radio‘s attempts at nostalgia mostly feel cheap and contrived, even with the help of Hoffman’s passionate rock-n-roll loving American DJ, ‘The Count’.

Where to Stream Pirate Radio

This movie really should have been a home run, but its only real saving grace is Hoffman. Opposite frequent collaborator Catherine Keener, he does create some sparks and intrigue, and his character is far and away the most interesting in the sadly boring A Late Quartet. As with many of the roles Hoffman played, his portrayal of a guy just waiting to catch a break still packs an emotional punch despite the lacking source material.

Where to Stream A Late Quartet

It may only be a cameo, but where else are you going to see Ricky Gervais, Louis C.K., and Hoffman in the same scene? Even in a comedy, Hoffman manages to bring a little bit of pensive melancholy – and unmatchable screen presence – to his short scene and completely steal a large chunk of a mildly flawed flick.

Where to Stream The Invention of Lying

Before it was gender-bent and Lara Jean Chorostecki tackled the role on Hannibal, Hoffman played supremely irritating reporter/tabloid drudge Freddy Lounds, a sleazy, naive man who evidently pays the ultimate price after cockily antagonizing the eponymous serial killer. There are a lot of problems with this Brett Ratner-helmed film, but Hoffman’s emotional, grating, occasionally creepy take on this character makes it worth the watch.

Where to Stream Red Dragon

It’s shocking that My Boyfriend’s Back isn’t on more essential 90s flick lists, because the Bob Balaban-directed film is way more fun than one might expect. Matthew Fox (Lost) stars as a popular high school kid so enthralled by the idea of going to prom with his dream girl that he even finds a way to accompany her after his death, and Hoffman is all-too-perfect as Fox’s ditzy, adoring, muscly henchman Chuck.

Where to Stream My Boyfriend's Back

“THE BEST MAN IS IN THE HOUSE!” is a sentiment that certainly proved to be true after Hoffman spoke the line, because aside from his performance, Along Came Polly is a relatively basic rom-com. We may know and love him for many of his dramatic, heavier films, but this flick adeptly demonstrated Hoffman’s ability to be a showstopper in the realm of physical comedy and supreme goofiness. As cocky former child star Sandy, he’s downright hilarious, and lifts up an otherwise predictable movie.

Where to Stream Along Came Polly

Hoffman’s willingness to embrace even the skeeziest of roles once again came into play with Next Stop Wonderland, a charming, little-seem rom-com in which he plays the entertainingly duplicitous, trashy ex-boyfriend of Hope Davis’ character. There’s a lot to unpack in Hoffman’s funny performance, but his overall look combined with the gross motives behind his actions make for a memorable turn for the actor.

Where to Stream Next Stop Wonderland

Even in another brief cameo role, Hoffman manages to completely hijack all happenings. Despite the comedy occurring around him, he plays Henry’s disturbing obsession with a colleague in a completely dramatic, furious tone, helping to drive the entire scene home in a bizarrely comedic way that few others can even dream of accomplishing.

Where to Stream Strangers with Candy

While a franchise adaptation of a young adult novel series may have seemed a strange choice for Hoffman, he evidently brought a much-needed sense of wisdom and humanity to the films. His role was introduced in the second film in the franchise as a rather small but important one, and the revelation that he’s actually fighting for the good guys later on made his performance even more compelling.

Where to Stream The Hunger Games: Catching Fire

Delightfully theatrical and thoroughly seedy, Hoffman’s womanizing, hypocritical Reverend Veasey might have seemed like strange casting choice had it not been for his total willingness to take it to bonkers, enthralling levels. “Big talker” is a moniker that could be used to describe a handful of Hoffman’s roles, but he somehow accomplished new things with the type every time.

Where to Stream Cold Mountain

While Hoffman’s collaborations with Bennett Miller are much better remembered in Capote, his turn in this other based-on-a-true-story tale was still a top-notch performance. Hoffman played the stony Art Howe, the real-life coach of the Oakland A’s set on doing things in his old, tried-and-true ways rather than adapting innovative ideas from Brad Pitt’s Billy Beane, the fresh GM. His role may be a supporting one, but he proves to be absolutely crucial in the progression of this quiet film.

Where to Stream Moneyball

Another gorgeous early display of the genius to come, Hoffman’s role as a neighborhood cop in this flick also starring Paul Newman and Bruce Willis makes us wonder how the late actor didn’t wind up playing more law enforcers over the course of his career. He’s on screen pretty briefly, but when he is, we’re wondering what he’s up to and what things might lie ahead for him.

Where to Stream Nobody's Fool

This HBO miniseries may seem like a distant memory, but Hoffman’s performance remains unforgettable. Based on the titular 2001 Richard Russo novel, the two-part miniseries tells the story of Miles Roby (Ed Harris), the seemingly content manager of the Empire Grill who has lived in the town all his life. Hoffman beautifully stars as Charlie Mayne, a mysterious man and evidently pivotal character in Miles life who carries a lot of significance – including why Miles has never left Empire Falls.

Where to Stream Empire Falls

The first of many stunning collaborations with Paul Thomas Anderson, Hoffman doesn’t even boast a real character name and still runs away with his few minutes of screen time in Anderson’s debut. Between his wonderfully awful getup, grating grin, and delight in tormenting Philip Baker Hall, Hoffman wasted no time in proving that he was ready to dazzle us in any way we asked of him.

Where to Stream Hard Eight

In what turned out to be Hoffman’s final role, he continued to gift us with a uniquely pragmatic and sensitive leader who understood our protagonist and attempted to ensure that all parties were content with the progression of their new world. Because Hoffman did not finish filming, some parts of his performance are CGI, but there’s no denying those expressive eyes when they fill up the screen and talk to Katniss about the treacherous state of things.

Where to Stream The Hunger Games: Mockingjay Part 2

With his directorial debut, Hoffman proved that he wasn’t any one-trick pony and managed to avoid the plight of many actors-turned-directors-of-themselves – Jack Goes Boating never feels too self-indulgent. As the eponymous Jack, Hoffman plays a rare, bumbling romantic lead opposite Amy Ryan. The movie is a steady, endearing one, and Hoffman elevates it to a place it may not have gone in the hands of another actor/director.

Where to Stream Jack Goes Boating

In his second go at the role, Hoffman brings more nuance and sensitivity to a chaos-filled franchise alongside the here-malicious screen partner (and frequent collaborator) Julianne Moore. The revelation of his true alliance and intentions to help build a better world give his character a surprising depth, and despite his limited screen time, he is armed with an emotional, intriguing character arc.

Where to Stream The Hunger Games: Mockingjay Part 1

It’s tough to shine when you’re amongst legends like Jeff Bridges, John Goodman, and more, but somehow, this small role became one of Hoffman’s most universally beloved. As Brandt, the unfortunate lackey to the grumpy, wheelchair-bound Big Lebowski, he’s smarmy, meek, and completely cringey all at once – a perfect Coen Brothers player. Who could forget that laugh?!

Where to Stream The Big Lebowski

In George Clooney‘s political drama, Hoffman may play the only character truly on the straight and narrow, and he does so with a fascinating, prudent sense of righteousness. As a veteran campaign manager who prioritizes loyalty above all things, he tries to steer his protégé (Ryan Gosling) in the right direction and keep everything afloat – until it’s too late. Many other actors might have taken on this role as a harsh, angry old-schooler, but Hoffman’s depth is truly something to behold here.

Where to Stream The Ides of March

Who knew “shut up” could be such a showcase for a brilliant actor? While Punch-Drunk Love is largely remembered for giving us one of Adam Sandler‘s best performances, the Paul Thomas Anderson flick also presents us with a menacing, greasy villain in Hoffman’s unrelenting Dean. This list really could have been a ranking of Anderson and Hoffman collaborations alone, because a look at any of their pairings demonstrate that these two men truly completed each other on a cinematic level.

Where to Stream Punch-Drunk Love

When Hoffman’s Gust Avrakotos spits out Aaron Sorkin‘s words in Mike Nichols‘ Charlie Wilson’s War, they bite, they sting, they smack you in the face. Between his totally thrilling delivery of dialogue and all-out physical performance, you’re left with no question about why Hoffman was nominated for an Oscar for playing Avrakotos (and really, really wish he’d gotten to do a little more Sorkin).

Where to Stream Charlie Wilson's War

The only animated character Hoffman ever played could not have been more suited to him. This beautiful, stop-motion animated film follows Max, a middle-aged man with Asperger’s who strikes up a pen-pal correspondence with a strange Australian girl, and Hoffman’s voice – ever so distinct, so sensitive – brought the same heart-wrenching, soul-searching quality he did to all of his on-screen roles.

Where to Stream Mary and Max

Spike Lee‘s critically-acclaimed exploration of a post 9/11 New York as one man (Edward Norton) experiences his last 24 hours of freedom with his childhood friends (Hoffman and Barry Pepper) before he turns himself in for a long prison sentence is a flooring film in many ways, helped in part by Hoffman’s type-breaking role in Jacob. The shy teacher overcome with unrequited longing for a 17-year-old student doesn’t seem like the kind of role that one would typically cast Hoffman in, but boy, does he fill it in a beautifully painful way.

Where to Stream 25th Hour

What a dream it would have been to see more Mamet from Hoffman, because State and Main is a total treat. Much like the way he bit down on Sorkin’s words in Charlie Wilson’s War, Hoffman embodied Mamet’s on-screen imagining of himself in a painstakingly earnest playwright who falls victim to the corruption of Hollywood. Despite everything thrown his way, Hoffman filled the role with a sense of lightness and commonality that was rarely seen amongst his work.

Where to Stream State and Main

This brutal neo-noir does not give us a sympathetic character in Hoffman’s Andy, but he is impossible to stop caring about. His desperate, in-too-deep heroin addict often seems to not fully grasp the implications of what he’s done, and the overwhelmingly heavy sense of dread over the film pushes Hoffman to a dark, fascinating place that’s difficult to see now knowing his fate.

Where to Stream Before the Devil Knows You're Dead

Viewers, beware: you won’t want to start this one without tissues handy. Another that’s difficult to watch because of Hoffman’s passing, his heartbreaking performance as a man who loses his wife to suicide and becomes addicted to the gas used in remote-control planes is absolutely gut-wrenching. There’s a lot of pain in this movie, and you can see it all in Hoffman’s eyes.

Where to Stream Love Liza

Oh, did he play those slimy guys well, and boy is it a delight to behold. Watching him get under Matt Damon‘s skin in The Talented Mr. Ripley offered a supreme case of schadenfreude, and his ability to play the life of the party who just ooooozes sexuality despite his lacking of unconventional good looks made Hoffman’s performance even more unforgettable (and enduringly enjoyable).

Where to Stream The Talented Mr. Ripley

Proving once again that he could fill the shoes of living, breathing people, this true story cast Hoffman as a sad, gambling-addicted man who managed to concoct a near-unprecedented embezzlement scheme to hide his addiction. What’s truly incredible about this performance is the surface-level poker face and the complete psychological dismantling occurring underneath it all that Hoffman manifested on screen.

Where to Stream Owning Mahowny

This breathtaking turn presents itself like a stage performance (because it mostly is), and that’s not a dig at John Patrick Shanley’s adaptation of his own play. Opposite a worthy sparring partner in the cold, stoic Meryl Streep, Hoffman’s passion as Father Brendan is absolutely thrilling, and the war of ice and fire at play between the two of them is something of a revelation.

Where to Stream Doubt

One of the last performances he ever gave speaks to the enduring quality of his work and his talent, and his subdued German accent and cold, calculating performance in this espionage thriller offered a glimpse into a unique side of Hoffman that we rarely got to explore. Hoffman’s ability to play someone both cautiously optimistic and entirely defeated at the same time remains unmatched.

Where to Stream A Most Wanted Man

I know, I know – a Mission: Impossible film in the top 10 seems crazy. But hear me out. Hoffman singlehandedly manages to make this movie chilling and interesting all at once. He’s sinister, intriguing, and absolutely terrifying, and there’s a raw sense of suaveness to him that makes him a perfectly unconventional villain who breaks what might have otherwise been a fairly tired formula.

Where to Stream Mission: Impossible III

Charlie Kaufman’s weird, wonderful directorial debut placed Hoffman in the shoes of a troubled playwright, and despite the near-inability to really categorize this flick into one genre, Hoffman plays both sides of the aisle with ease. Sure, Kaufman may get carried away with his sense of surrealism, but the weight and misery brought to the role by Hoffman keeps the film grounded no matter how wild it wants to be.

Where to Stream Synecdoche, New York

Laura Linney and Hoffman are near-perfect opposite one another in The Savages, a strangely funny exploration of a brother-sister dynamic that makes to be smart, emotional, and memorable all at once. As Jon, Hoffman fully embodied the conflicting, confusing emotions of dealing with an ill parent, his own depression, and familial relationships all while attempting to get through the day.

Where to Stream The Savages

Hoffman should have won many Oscars, but the one that finally did leaves no questions as to why he walked home with that golden statue. The actor truly poured his everything into manifesting the iconic author; his voice, physicality, and raw emotion all combined to make for what became one of the most stunning performances Hoffman ever gave. It’s no walk in the park to play a real person, and the way Hoffman captured Capote’s social quirks and supreme loneliness is difficult to shake, even days after watching the film.

Where to Stream Capote

It may seem strange to place a role so seemingly small so high up on the list, but this Anderson-Hoffman collaboration once again showed us that Hoffman could play a sleazeball one moment and a sad sack the next and pull at our heartstrings in way we never imagined. As Scotty J., the gay crew member of the film’s central porn flick team, Hoffman never comes close to becoming a caricature or footnote as he harbors an unrequited crush on Dirk Diggler (Mark Wahlberg). In Boogie Nights, he shines in both early moments of humor and later instances of despair, and turns Scotty into a dimensional, sensitive character that easily gains our empathy and support.

Where to Stream Boogie Nights

Pervy as he may be as Allen in this wildly wacky film, Hoffman’s ability to play a fundamentally miserable outsider is perfectly utilized in Happiness, a flick that finds him prank calling to express his dirtiest desires and hide behind the telephone wire. He’s uncomfortable in his skin, he’s sweaty and confused, he’s totally petrified of what face-to-face interaction means – so when it happens, watching Hoffman’s worst fears manifest on his face is almost heart-stopping.

Where to Stream Happiness

The ensemble in Paul Thomas Anderson’s 1999 emotional Los Angeles epic made it hard to stand out, but even in his smaller supporting role, Hoffman perfectly brought vulnerability, awkwardness, and devotion to every moment he breathed on screen. A viewing of any scene he’s present in over the course of Magnolia‘s 3 hours makes it clear that his heart is fully in this project, and watching him fight for the man he’s caring for and eventually fall prey to his own emotions as he witnesses this progression of events almost certainly puts viewers on a roller coaster of empathy. Phil Parma is all of us, more than any of the other characters in the movie; he’s not perfect, but he’s not harboring some big, deep, dirty secret, either. He’s filled with compassion and the desire to give people what they most desperately want, and his own desperation and big, bleeding heart is put on full display in Hoffman’s voice, in his eyes, in the way he carries himself whenever he’s on screen.

Where to Stream Magnolia

There’s a lot that’s wonderful about Almost Famous, but it’s probably safe to say we can credit Hoffman in large part for turning it into the phenomenon that it became. Cameron Crowe’s semi-autobiographical coming-of-age story puts Hoffman in the shoes of Lester Bangs, a legendary rock journalist who puts a philosophical lens on the world and is damn-near bursting with compassion. It’s almost frustrating to watch the film when you realize how little he’s actually in it, but his messages of self-acceptance, and the value of being uncool, no matter how hard everyone else is trying to reach peak coolness – is the perfect legacy for Hoffman, who made a career out of playing accessible, strange characters. It’s the perfect embodiment of the persona he presented to us over the course of his on-screen performances, and that’s why it’s so transcendent and incredibly memorable.

Where to Stream Almost Famous

There is something about Hoffman’s captivating cult leader in The Master that almost makes his loss sting more than any of his other roles. In what is seemingly Paul Thomas Anderson’s take on Scientology, Hoffman stars as Lancaster Dodd, the charismatic leader of “The Cause” who takes the troubled Freddie Quell (Joaquin Phoenix) under his wing. He takes Freddie on as something of a surrogate son, treating him as such when he misbehaves. There’s a magnetism, a wildly compelling quality to Hoffman every second he’s on screen – and the film would not work if it weren’t for this. You have to believe that these normal, intelligent people would throw it all away to follow this captivating leader, and you do – all because of what Hoffman does in every moment. Whether he’s giving a grand, stirring speech, losing his cool and calling someone a “pig fuck”, or emotionally singing as he bids farewell to his temporary child, every single matchless moment is a testament to why Lancaster Dodd is the greatest part Hoffman ever played. There’s a majesty, an enduring, breathtaking quality to his performance here, to his laughter when he rides the motorcycle through the open plains, to his pensive, furrowing brow as he examines members of his following, to his frustration with Freddie when he strays from the path but knows he just can’t shake the addiction they have to each other.

There’s no other way to describe what Philip Seymour Hoffman does in this film but “magic”, plain and simple. Because that’s what the man was – he was magical, magical in every sense of the word, and the world got a little less so when we lost him. Lucky for us, however, he left a lot of it behind.

Where to Stream The Master