Photo-Illustration: Maya Robinson

The culture-wide sense of sadness engendered by Philip Seymour Hoffman’s death of an overdose at 46 in February 2014 has never gone away, or even dissipated. Nearly two years after news of his passing shocked and saddened viewers, it remains a fresh wound. If you are even a casual movie fan, chances are good that Hoffman starred in one of your favorite movies. If you’re a cinephile, then it’s likely the actor plays a central role in many of your fondest movie memories of the past quarter decade.

The loss of an artist of Hoffman’s caliber — he was no mere actor; both collectively and individually, his work allowed us to understand ourselves and our world better — is incalculable. That loss has felt particularly intense as Hoffman’s last remaining films have trickled out; alas, Hoffman does not have a Tupac-like deluge of unreleased posthumous material left (nor did directors possess the shamelessness to digitally enhance what was left behind). Accordingly, today’s release of The Hunger Games: Mockingjay Part 2 — the final film Hoffman made — gives a world that never stopped mourning Hoffman another opportunity to celebrate one of the greatest actors of all time.

With that in mind, we figured this would be a good time to delve deep into Hoffman’s filmography to determine what art of Hoffman’s is objectively, definitively better than his other art. In making our selection, we considered both the quality of the film as well as Hoffman’s performance. Though we strived to be as complete as possible, we were not able to see Mockingjay Part 2 ahead of this article, nor were we able to track down two of his most obscure early films, Szuler and Joey Breaker, left behind in VHS format. We still, however, had an awful lot to sift through, much of it awfully good.

51. Patch Adams (1998)

Patch Adams doesn’t just belong on the bottom of a ranked list of films by a great actor like Philip Seymour Hoffman; it’d belong on the bottom of any ranked list, regardless of context. The sole collaboration between Robin Williams and Hoffman was an enormous commercial hit that has been appropriately pilloried as the unwatchable nadir of Williams’s tendency toward shameless schmaltz. Not even Hoffman’s ornery performance as an early roommate of the good doctor, seemingly the only person not utterly charmed by the protagonist’s zany cult of personality, can redeem this, especially since his character disappears for a long stint, then returns as just another captivated fan of the titular wisecracking yet tender-hearted medical professional. The great thing about Hoffman’s career is that Patch Adams is a glaring anomaly in a life otherwise fiercely devoted to pursuing truthful roles and pushing himself to the brink of his extraordinary abilities. The tragic thing about Robin Williams’s intermittently brilliant but far more checkered career is that Patch Adams was the rule rather than the exception.

50. Triple Bogey on a Par Five Hole (1991)

Hoffman made his film debut in 1991’s Triple Bogey on a Par Five Hole, a black-and-white crime opus with unfortunate aspirations to be Citizen Kane on a budget that, unfortunately, lives up to the groaning pretension of its title. Playing a scuzzy pool-hall low-life named Klutch, Hoffman cackles maniacally for no discernible reason in a blink-and-you-miss-it role that is the film’s sole claim to fame. Hoffman’s appearance is defined by his wardrobe more than his dialogue. When you’re introduced rocking a sleeveless T-shirt, studded, fingerless motorcycle gloves, and a sweet-ass bandanna, there’s nowhere to go but up — though few could have imagined then the heights to which Hoffman’s career would soar.

49. Montana (1998)

In the aftermath of the culture-wide explosion of Tarantino mania in the mid 1990s, the fringes of bloody American genre-movies were filled with knockoffs nakedly trying to recapture Quentin’s bleakly funny, hyperbolically macho brand of tough-guy cinema. None of them were as good as Tarantino but many of them were just as bad as 1998’s Montana, a muddled crime movie that wastes a terrific cast (Hoffman, Stanley Tucci, Robbie Coltrane, John Ritter, Mark Boone Junior) on a rancid, self-infatuated screenplay about the machinations among a group of scuzzy criminals. In one of his most negligible performances, Hoffman plays oily money man Duncan, who is craftier than the short-tempered hoods in his circle, but, as was often the case with Hoffman’s scheming characters, not quite as crafty as he imagines.

48. Flawless (1999)

Robert De Niro. Philip Seymour Hoffman. Joel Schumacher. Two of those three men are among the most revered and brilliant artists of their time. The third directed Batman & Robin. Unfortunately, the Joel Schumacher factor far outweighs the pairing of De Niro and Hoffman in the mismatched buddy drama Flawless, a movie whose premise (ornery homophobe takes voice lessons with a soulful drag queen, life lessons ensue) sounds like it has the potential to be a compelling, 1970s-style exploration of life on the fringes and the strange bedfellows it creates. Instead, the film plays more like a lumbering TV movie that takes forever to clumsily deliver the message that drag queens are people, too, even if it takes close-minded bigots like De Niro’s character some time to accept that incontrovertible fact. Hoffman gives the role of a melancholy drag queen and vocal coach his all, but fails to elevate the proceedings. Seldom, if ever, has Hoffman done more acting in the service of an innately doomed project.

47. The Party’s Over (2001)

Who was Philip Seymour Hoffman? Fans came to feel like they knew him through his art, but for a man who made such a profound impression on the world of film, precious little was known about him as a person. That’s part of what makes the political documentary The Party’s Over so oddly revealing. A follow-up to 1993’s The Last Party, a similar political documentary made by Robert Downey Jr. (an actor whose personal life audiences know, if anything, far too much about), The Party’s Over is interesting today less for the nonexistent insight it provides into the American political process than for the insight it provides into Hoffman, who emerges as a sweet, passionate, and curious man, and, alas, just about the last person qualified to host a political documentary.

46. Twister (1996)

Hoffman’s supporting turn as a storm-chasing weather freak in the enormously popular early-CGI extravaganza Twister hints at an alternative future for the actor in which he wouldn’t be known as a heavyweight thespian revered by the greatest talents of the day, but rather a red-headed goofball screwing around affably on the margins of major motion pictures. Thankfully, that was not to be, and Twister, like Along Came Polly, stands as an outlier in this very serious man’s very serious (but often hilarious) career. Along Came Polly at least has the benefit of a great, humorous performance by Hoffman, whereas the nicest thing that can be said about Hoffman here is that at least he’s not boring. Tacky, silly, and broad? Sure. But boring, he is not.

45. Scent of a Woman (1992)

It’s faint praise to argue that Hoffman’s performance as an oily-prep school creep who tries to manipulate Chris O’Donnell’s scholarship twerp in Scent of a Woman is the element of the film that holds up best today, because other than the film’s cinematography, it’s the only part of the film that doesn’t feel glaringly, egregious false. This includes Al Pacino’s obnoxious performance as a nightmarish sentient shout of a man dead set on getting the actor playing him an undeserved Academy Award. Though Pacino and O’Donnell are supposed to be the heroes (or anti-heroes at least) of the film, they’re so insufferable that they inspire sympathy for Hoffman’s guileful if overmatched antagonist by default.

44. The Getaway (1994)

As a young film actor, Hoffman paid his dues with plenty of lowlife roles that exploited the actor’s sweaty intensity and bruising physicality but otherwise proved equally untaxing and unrewarding. That’s the kind of role Hoffman played in Roger Donaldson’s adaptation of Jim Thompson’s The Getaway, which had previously been adapted by Sam Peckinpah in a memorably reprehensible exploration of the seedy depths of human depravity. Hoffman fits right into his scuzzy environments, but thankfully his days of adding some color and bite to gruff, working-class bit roles was drawing to a close by the mid-’90s.

43. Along Came Polly (2004)

Hoffman’s participation in the Mission Impossible and Hunger Games franchises illustrates that he was not entirely averse to picking up a nice paycheck in a big commercial movie that might play somewhere outside art houses, but the actor’s career is remarkably slim on movies clearly made for commercial reasons. That’s part of what makes Hoffman’s performance as a hilariously overconfident former child star in Along Came Polly so refreshing. Hoffman proves himself a surprisingly deft and confident physical comedian, but his wonderfully loose and goofy performance only elevates this pandering, formulaic Jennifer Aniston–Ben Stiller rom-com to the level of affable mediocrity.

42. Pirate Radio, aka The Boat That Rocked (2009)

It’s tempting to imagine what Lester Bangs, that preeminent martyr of musical good taste and journalistic integrity, whom Hoffman played so unforgettably in Almost Famous, would have made of the cheap, easy rock and roll and 1960s nostalgia of Richard Curtis’s Pirate Radio. Chances are good he’d find the film’s cartoonish deification of ‘60s rock rebellion self-aggrandizing, bland, and mediocre, even if Hoffman’s performance as “the Count,” an American DJ flying the flag for good, old rock and roll on a British pirate radio station, gives this sentimental nonsense what little genuine passion it possesses.

41. God’s Pocket (2014)

There is a certain kind of grim, intentionally modest art film that needs the peculiar oxygen and generosity of spirit found at film festivals (particularly Sundance) in order to live, and dies an unmourned death in the real world. One such film is God’s Pocket, the directorial debut from Mad Men silver fox John Slattery, which Hoffman produced as well as co-starred in as a small-time neighborhood criminal terrified of losing what little he has. It’s a grungy adaptation of a Pete Dexter novel set in the early days of the Reagan era, a well-acted and grim exercise in grubby miserablism that never quite justifies its existence, despite the quality of the people involved.

40. Money for Nothing (1993)

Even when Hoffman’s early films weren’t remarkable, their casts almost always were. It’s difficult to envision a major motion picture more minor than Money for Nothing, a low-budget shrug of a movie in the low-stakes, low-energy, low-yield Touchstone mode about a real-life nobody who finds over a million dollars and then must wrestle with the ramifications of his discovery. Playing a small-timer who’s sharper than his lummoxlike exterior would suggest, Hoffman is joined by a preposterously overqualified supporting cast that includes Michael Madsen, Debi Mazar, Benicio Del Toro, Michael Rapaport, James Gandolfini, and Maury Chaykin, all of whom were destined for bigger and better films.

39. Leap of Faith (1992)

Leap of Faith once again finds a young, attention-hungry Hoffman in a small but memorable supporting role as a small-time criminal, but this time around the criminal enterprise he’s involved in is of an unusual variety. In this promising but underwhelming comedy-drama, Hoffman plays part of a roving band of charlatans and con artists who fleece the faithful at the behest of a sham healer and evangelist played by Steve Martin. The sections of the film devoted to Hoffman and his partners in crime are colorful and engaging, but the central dynamic is a non-starter, the dramatic elements of the film only dragging it down further.

38. A Late Quartet (2012)

How do you make the once-in-a-lifetime teaming of Philip Seymour Hoffman and Christopher Walken a non-event? Get them to star in a film called A Late Quartet, whose PBS-pledge-drive-ready title all too accurately captures the tone and tenor of the film: refrained, highbrow, and respectably, artfully boring. Essentially, the material does not rise to the level of the actors in the film. Of the respected thespians playing the titular quartet of musicians wrestling with decades of resentment, Hoffman has the most to work with, however. His character’s raw yearning for his day in the sun after an endless expanse of patiently waiting is all that breaks through the film’s tasteful tedium.

37. When a Man Loves a Woman (1994)

Addiction was a theme in Hoffman’s career dating back to his pre-stardom days. Before Owning Mahony, before The Devil Knows You’re Dead and Love Liza, Hoffman co-starred in this drama as a recovering alcoholic whose bond with a depressed wife (Meg Ryan) threatens her husband (Andy Garcia). Hoffman portrays the sober side of things rather than, as we’d see in later films, someone in the grips of a compulsion with the potential to destroy him, but his portrayal of the complicated emotions of addiction is just as effortlessly authentic.

36. The Ides of March (2011)

By the time he played a veteran political operative trying to stay one step ahead of a game that changes mercurially and without reason in 2011’s The Ides of March, Hoffman was a man with character, someone who knew a thing or two about the way the world works. That experience informed his performances, particularly when playing characters who were similarly masterful and committed to their craft, like his canny old professional of a veteran campaign strategist, who only realizes how thoroughly outmaneuvered he is until it’s too late to do anything about it.

35. Red Dragon (2002)

There was absolutely no reason whatsoever that Thomas Harris’s Red Dragon needed to be adapted for film by Brett Ratner when the somewhat more talented Michael Mann already brought it to life in the suspense masterpiece Manhunter. The only conceivable reason, beyond commerce and the public’s unending fascination with all things Hannibal Lector, is the opportunity the film provides for Hoffman to channel the sleazy, oily, Über-cynical sleazebag within in his super-fun performance as scuzzy tabloid hack Freddy Lounds, who ends up paying a terrible price for unwisely antagonizing a deranged serial killer played with frothing-at-the-mouth hamminess by an awful Ralph Fiennes. Hoffman gives this lurid potboiler a glorious burst of creepy energy that dissipates the moment he dramatically exits the proceedings.

34. Cold Mountain (2003)

God bless Anthony Minghella. He looked at Hoffman’s sizable frame and unconventional ginger looks and saw an unrepentant womanizer giddy off undeservedly high self-esteem. Minghella memorably cast Hoffman as a slick international playboy in The Talented Mr. Ripley and reunited with the actor for Cold Mountain, where Hoffman plays a big-talking preacher whose personal sins don’t exactly jibe with the piousness of his profession. Hoffman delivers a wonderfully theatrical, flashy performance that gives a jolt of life to what is otherwise a ponderous, overwrought, and lumpen epic.

33. My New Gun (1992)

The old cliché about there being no small roles, only small actors, certainly applied to a pre-stardom Hoffman, who stopped just short of staring at the camera and winking to make sure that audiences remembered him, no matter how forgettable the circumstances or how seemingly inconsequential the role. The sly sleeper comedy My New Gun is a cut above most quirky 1990s independent fare, and it’s never better than during Hoffman’s magnetic bit turn as a small-timer with a very big attitude and a peculiar conversational approach. He’s a real character, played by a man who would go on to become one of our greatest character actors.

32. The Invention of Lying (2009)

Hoffman contributed a goofy cameo in the comedy The Invention of Lying, as a bartender in an alternate universe where everyone is relentlessly and graphically literal in their honesty; he proves an easy mark for the first man in this universe to discover the necessity of fibbing. The Invention of Lying is worth seeing if only for the opportunity to witness Louis C.K., Philip Seymour Hoffman, and Ricky Gervais share a scene, but it’s worth noting that even when Hoffman lent his talents to a comedy, it was in an achingly sad, philosophical fantasy meditation on the essence of truth that irreverently posits God as a lie the world tells in an attempt to distract itself from the infinite pain of existence.

31. Strangers With Candy (2005)

Even when popping up briefly for a cameo in a low-budget adaptation of a cult TV comedy, Hoffman still couldn’t escape the claustrophobic psychodrama of his dramatic performances. In his bit part in the Strangers With Candy movie, Hoffman plays an a school-board member less interested in educational excellence than in divining the sexual history of a colleague he’s clearly unhealthily obsessed with. Hoffman plays his character’s anger and confusion completely straight, which of course makes it even funnier.

29. My Boyfriend’s Back (1993)

Considering the current mania for all things zombielike and undead, the surprisingly clever 1993 zombie high-school rom-com My Boyfriend’s Back is begging for a remake. The film, character actor Bob Balaban’s follow-up to his directorial debut Parents, takes a wonderfully deadpan approach to the darkly comic tale of an earnest young man so excited that the girl of his dreams agreed to go to the prom with him, he isn’t about to let anything as minor as his own death get in the way of that perfect date. Hoffman plays the dumbest and muscliest of his early dumb-muscle roles, this time as the adoring henchman of a high-school creep played by Matthew Fox, but it’s doubtful a theoretical My Boyfriend’s Back could top the cast of the original, which includes not just Hoffman and Fox but also Matthew McConaughey, Cloris Leachman, Austin Pendleton, Paul Dooley, Edward Herrmann, and Mary Beth Hurt.

28. Next Stop Wonderland (1998)

Brad Anderson’s Next Stop Wonderland was such a Sundance sensation that when he purchased it, Harvey Weinstein famously said he wasn’t just buying a single movie; he was “getting into the Brad Anderson business.” That turned out to be a business with exceedingly limited commercial potential, but that doesn’t mean Next Stop Wonderland isn’t still a charming, wry, and low-key romantic-comedy sleeper with a wonderful lead role from Hope Davis and a hilarious supporting effort from Hoffman as her hypocritical phony of an ex-boyfriend, a sleazeball with a Whole Foods–ready exterior but an Axe Body Spray soul.

27. The Hunger Games: Catching Fire (2013)

The fact that Hoffman’s final film is an entry in a billion-dollar dystopian sci-fi franchise attests to the fact that even for an actor as serious as Hoffman, it wasn’t all about art films and scuzzy character studies. Yet even when Hoffman lent his considerable gifts to a lucrative series of surefire blockbusters, he chose a project that reflected his own sensibility, in a way. For all its commercial elements, The Hunger Games is grim, challenging, and unrelentingly dark (as befits a franchise about kids killing each other in a legally mandated spectacle), and it gave Hoffman both great actors to play off of and a complicated character to portray in Plutarch Heavensbee. He’s a savvy political operative who is introduced in a small but crucial role in The Hunger Games: Catching Fire, but would go on to play a much bigger, even more essential role in the films that followed, after it was revealed that Plutarch wasn’t a sinister figure of mystery and menace behind the ruling powers but rather a rebel in disguise.

26. Moneyball (2011)

With Capote, Hoffman and director Bennett Miller had — in Truman Capote exploring the shadowy real-life crime tale that would inspire In Cold Blood — a story so famously compelling that it inspired two competing versions released around the same time, one with Hoffman in the lead, the other with Toby Jones. Moneyball found Hoffman and Miller working together on another ripped-from-reality tale, but this time it’s one so wonky and seemingly non-cinematic — a general manager using a complicated mathematical formula called “Sabremetrics” to win games — that it’s hard to believe it got made in the first place. Hoffman has a supporting but crucial role in Moneyball as real-life Oakland A’s manager Art Howe, a Swanson’s Hungry Man TV dinner of a guy whose old-school approach violently conflicts with the newfangled techniques of statistics-crazed GM Billy Beane (Brad Pitt).

25. Capote (2005)

Several of Hoffman’s most memorable performances were as writers. Though he began his career playing a lot of lumbering thugs, by middle age, he had a cerebral presence that made it easy to imagine he possessed a psyche full of rich, vivid worlds waiting to be splashed onto the page and devoured by readers. Hoffman played a writer whose ambitions overtake him in Synecdoche, New York, and a lovable intellectual in for a rude real-life education amid the ruthless pragmatism of show business in State & Main, but his most notable performance as a writer was his Oscar-winning turn as Truman Capote in Capote. It’s not easy playing a real-life figure the world not only knew well, but knew as a dizzy perpetual exercise in self-parody. Hoffman captures Capote’s ebullience — that sense that he brought the party with him everywhere he went — but also the fundamental loneliness of a man doomed by his own relentless self-interest to lead a solitary existence, despite the famous names in his social circle.

24. Mission: Impossible 3 (2006)

The underrated third entry in the Mission: Impossible franchise didn’t just give Tom Cruise’s supersecret agent Ethan Hunt a nemesis worthy of him, it provided an enemy so terrifying in his nastiness that it rendered Hunt an underdog by default. Hoffman played blinding arrogance as compellingly as he did insecurity and self-loathing, perhaps because he understood that they come from the same place. As Hoffman-Cruise team-ups go, Mission: Impossible 3 doesn’t quite measure up to Magnolia, but that’s because Magnolia is achingly sincere, transcendent art while Mission: Impossible 3 is merely crackerjack entertainment.

23. A Most Wanted Man (2014)

Philip Seymour Hoffman. Anton Corbijn. John le Carré. When these three grim human beings united for A Most Wanted Man, it stood to reason that the results would not be defined by an excess of warm life lessons and hugs. No, A Most Wanted man is a purposefully cold and methodical espionage film awash in ambiguity and complexity that casts Hoffman as a brilliant, hard-drinking counterterrorism operative who is overwhelmed and defeated by an international game that chews up and spits out even savvy players of his experience and skill.

22. Charlie Wilson’s War (2007)

For such a cerebral performer, Hoffman was also an intensely physical actor. Moreover, his physicality often reflected the characters he was playing: that too-tight shirt over a none-too-trim belly defines Boogie Nights’ Scotty on a tragicomic level (and, I would argue, belongs in the Smithsonian, alongside other artifacts from Hoffman’s career). Hoffman’s slovenly doughiness at times added an additional element of pathos and defeat to the sad strivers he often played, but in his performance in Mike Nichols’s juicy, if mildly underachieving, Charlie Wilson’s War, Hoffman’s physique only makes spy Gust Avrakotos even more intimidating. Hoffman plays Avrakotos as a man who could probably get run over by a tank and suffer only a few minor scratches, but if the character is physically a force of nature, he’s even more explosive on a verbal level. He’s the kind of person who can destroy lesser souls with a few perfectly chosen and delivered words, and in a predictably Oscar-nominated turn of incandescent flashiness, Hoffman transforms Sorkin’s monologues into profane, propulsive poetry.

21. Jack Goes Boating (2010)

The cliché goes that Hollywood doesn’t make intimately observed, small-scale character-study movies about the lives of ordinary people anymore, but the truth is this kind of modest, deeply human film has never exactly been in vogue with audiences or studios. Jack Goes Boating, Hoffman’s directorial debut, is a proud throwback to the Paddy Chayefsky school of working-class realism embodied by Marty, which the film sometimes recalls. The film affords Hoffman a rare and unexpected opportunity to play a romantic leading man, albeit of the awkward and shambling variety. The knock on actor showcases like this (especially when they’re directed by an actor) is that they exist solely for the sake of acting, but when the acting is this consistently brilliant, and the storytelling so even and endearing, that’s a strength more than a weakness.

20. State and Main (2000)

Philip Seymour Hoffman and David Mamet aren’t exactly known for their gentleness. They are instead two men renowned for their intensity, fierce devotion to craft, and canny understanding of human nature’s dark side (and in the case of Mamet, regrettably, his shrill right-wing politics). Yet these two Serious Artists’ sole cinematic collaboration is unexpectedly, wondrously charming and wry. In Mamet’s lovingly written satire of Hollywood’s self-serving myopia, Hoffman plays Mamet’s surrogate, an earnest playwright who signs on to write a script and is gradually corrupted by the moviemaking process, yet retains an uncharacteristic everyman quality all the same. State and Main suggests Hoffman could have had a career as a light romantic-comedy leading man (had Hollywood allowed it), but this turned out to be a delightful anomaly in Hoffman’s oeuvre.

19. The Hunger Games: Mockingjay, Part 1 (2014)

Hoffman had a small but pivotal role as rebelling Gamemaker Plutarch Heavensbee in The Hunger Games: Catching Fire, but that role feels like little more than a warm-up to his much more substantive role in its follow-up, where Plutarch’s plan falls into place. Hoffman’s character has a surprisingly satisfying and comprehensive emotional arc, considering his limited screen time. He’s a much different figure here than he was in the previous entry, and this expansion in screen time and shift in allegiances brings with it a new depth to the character.

18. Love Liza (2002)

The fact that Hoffman died of a drug overdose makes this heartbreakingly intense performance as a man who fakes an obsession with remote-control contraptions as a cover for his addiction to the gas used in remote-control planes, only to discover that he genuinely does love all things remote-control, hard to watch. But Love Liza would be tough to sit through regardless of the circumstances. As was his custom as an actor, Hoffman got uncomfortably close to the character of Wilson, a man who has given himself over to hopelessness following his wife’s suicide before fate pulls him in an unexpected direction. Hoffman’s passionate engagement with the almost unbearably painful emotions at the core of the narrative make this one of the most convincing depictions ever of grief, depression, drug addiction, and remote-control-airplane fandom.

17. Nobody’s Fool (1994)

Considering how substantively they figure in pop culture, it’s a little surprising that Hoffman did not play more cops. But he played a neighborhood cop in 1996’s Nobody’s Fool, a perfectly realized adaptation of Richard Russo’s wry novel about a lovable old coot played by Paul Newman (in a wonderful late-period turn) and his complicated relationship with the small town he lives in, his ornery boss (Bruce Willis), and Willis’s wife (Melanie Griffith), whom Newman lusts for openly. Though he doesn’t have much screen time, acting in Nobody’s Fool afforded the passionate young Hoffman the chance not just to share the screen with one of his idols (Newman), but also to get punched out by a man decades his elder, an honor Major League Baseball fans know as the “Robin Ventura special.”

16. Punch-Drunk Love (2002)

Paul Thomas Anderson drew extensively on Adam Sandler’s persona as a rage-filled everyman in Punch Drunk Love. Yet part of what makes the film so fascinating is that Sandler, who played the rage and tenderness-filled hero, and Hoffman, who played its pathetic yet menacing heavy, could easily have switched roles. After all, Hoffman has extensive experience playing outsiders imprisoned by their own neuroses and self-consciousness, like the film’s protagonist, and Sandler is similarly adept at expressing incoherent rage. For two seemingly antithetical figures, Hoffman and Sandler overlap a surprising amount; their pairing is part of what makes the film such a glorious anomaly in Sandler’s career, and yet another masterful collaboration between a director and an actor who invariably brought out the best in each other.

15. Hard Eight (1996)

When a movie star accepts an exceedingly small part in a film, it’s considered a cameo. When an unknown does the same, it’s just a bit part. Though he’d appeared in a few films, including one iconic hit (Scent of a Woman), Hoffman was a lot closer to an unknown than a star when he showed up in a casino with a shit-eating grin and some awesomely terrible clothes to taunt Philip Baker Hall’s elegant, haunted gambler Sydney in Hard Eight, Paul Thomas Anderson’s brilliant directorial debut. Yet despite his relative anonymity, Hoffman contributed what is unmistakably a star turn, a few minutes of razzle-dazzle from a young man keenly confident in his own prodigious gifts. Hoffman’s roles in Anderson’s films would get much larger, but from the very beginning, theirs was a charmed partnership.

14. Happiness (1998)

Hoffman frequently played outsiders uncomfortable in their own skin, but in the ironically titled Happiness, he went even further, playing a man for whom every breath feels almost unbearable, every moment an eternity of misery. He’s a prank caller who uses the telephone’s safe distance to at once satiate his perverted desires and protect himself from the terror of face-to-face communication, only to have the successful, bored woman he’s been menacing (Lara Flynn Boyle) seek him out and subject him to the ultimate horror: being rejected in person by someone he’s both attracted to and deeply afraid of. Hoffman plays a man imprisoned in his own sweaty, pale skin, cursed with thoughts and impulses he cannot control or understand.

13. Doubt (2008)

In Doubt, John Patrick Shanley’s adaptation of his own Pulitzer- and Tony-winning play (not to mention his long-awaited cinematic follow-up to Joe Versus the Volcano), Hoffman plays a priest in the early 1960s whose charisma and progressive ideas about the world and the church’s place in it threaten a joyless scold of a nun played by Meryl Streep in ways she simply cannot abide. As a filmmaker, Shanley doesn’t do much to open up his play, but when you have performers of this quality and a script this intricately wrought and nuanced, the oft-pejorative adjective stagey stops being a criticism and becomes purely descriptive.

12. Before the Devil Knows You’re Dead (2007)

After a supremely checkered ’90s and ’00s, Sidney Lumet ended his lengthy directorial career with Before the Devil Knows You’re Dead, a movie that reconnected him to the brutal, hard-edged psychological realism of his 1970s work. It’s a nasty neo-noir rich in atmosphere and light on sympathetic characters: Hoffman plays a heroin addict whose cursed existence grows even more perilous when a poorly thought-out scheme to rob his parents’ jewelry store turns deadly and threatens to implicate him. An intense air of fatalism hangs over the film, specifically the sense that its characters have all committed sins that will condemn them to hell no matter how badly they try to wiggle themselves out. For Hoffman’s desperately sad schemer, the oblivion found in a needle of heroin is preferable to anything else in this sick, sad world, his miserable addiction blinding him to anything but his own selfish needs.

11. The Savages (2007)

American cinema is distressingly devoid of smart, sensitive explorations of the complicated emotions of adult siblings, which makes movies like You Can’t Count on Me and the bleakly funny The Savages all the more welcome. As a grown-up brother and sister called upon to help take care of a dementia-addled father (Philip Bosco) who was never too concerned with taking care of them as children, Hoffman and Laura Linney create characters who are both united and divided by a complicated web of affection, emotional dependence, resentment, jealousy, and, yes, even love, that stretches back decades and informs everything they do in the present. It’s a low-key character study that captures the alienation of depression and ennui on a visceral level.

10. Mary & Max (2009)

Though it debuted at Sundance, the beautifully sad, sadly beautiful Australian stop-motion animated film Mary & Max never received theatrical distribution here in the States, yet went on to find a rich cult following all the same (users on IMDb rate it as one of the 200 greatest films of all time). It’s easy to see why. As Max, a middle-aged Jewish man with Asperger’s syndrome who becomes unlikely pen pals with an awkward little Australian girl, Hoffman and the animators create a character that is unique and specific, shaped both by his environment and his unusual brain chemistry, yet also strangely relatable in his longing for human connection. Mary & Max finds Hoffman in an unfamiliar role in some ways: He’d never provided the lead voice in an animated film, stop-motion or otherwise, before, and would never do so again. Yet the film keeps with the rest of Hoffman’s filmography in that it finds him getting deep under the skin of a heartbreakingly human character as he tries to understand the complexities of a cruel world and his place in it.

9. Magnolia (1999)

When you make a magnum opus while still in your mid-20s, what do you do for an encore? If you’re Paul Thomas Anderson, you follow up the feverishly ambitious Boogie Nights with the somehow even-more-ambitious Magnolia, and give your troupe of absurdly gifted repertory players another edict to bare their souls. For Hoffman, that meant trading in Scotty’s too-tight attire for the less flashy but just as challenging role of Phil, a good guy tasked with bearing witness to someone unpacking a lifetime of regrets before death renders that level of confession impossible. Anderson needed an actor who could match the presence of a titan of the craft like Jason Robards in his final role, and was eminently justified in thinking Hoffman was an actor of that caliber. It’s tough to watch their scenes together now that they’re both gone, but as with so much of Hoffman’s brutally intense filmography, it was pretty tough to watch scenes in that high of an emotional register even at the time of Magnolia’s release.

8. The Talented Mr. Ripley (1999)

Hoffman spent much of his film career suffering soulfully in a variety of tragic and tragicomic contexts. He was able to inhabit the complete range of human emotions across many kinds of characters, but he didn’t get to play sexy very often. In Anthony Minghela’s brilliant psychodrama The Talented Mr. Ripley, however, Hoffman exuded brash, cocky sexuality (he’s introduced expressing a desire to fuck every woman he meets) as a debonair continental playboy whose life is all about good food, good music, good clothes, and good sex. He’s a man for whom life is one wild party that begins to come to a close once he encounters the title character (Matt Damon), a sociopathic social-climber who wants what Hoffman and a buddy played by Jude Law have, and is more than willing to kill for it. Of course, Hoffman wasn’t quite as conventionally attractive as Law or Damon, but what he lacked in looks, he made up for in attitude.

7. Owning Mahowny (2002)

Addiction has seldom looked as captivatingly mundane as it does in the riveting 2002 Canadian drama Owning Mahowny, which told the stranger-than-fiction story of a sad brown Sears suit of a numbers-cruncher, who orchestrated one of the largest embezzlement schemes in Canadian history in order to cover up his gambling addiction. A tragically mustachioed Hoffman makes for a perversely non-perverse addict, a man whose intentionally dreary exterior purposefully masked a life ruled by an insatiable urge for self-destruction. His performance is appropriately internal, but there are heartbreaking moments throughout when the character’s cultivated poker face gives way to an expression that betrays his psychological unraveling as his secret life gets harder to control and keep separate from his humdrum everyday existence.

6. Synecdoche, New York (2008)

When it comes to human suffering, Sisyphus had nothing on Caden Cotard, the brilliant and troubled playwright Hoffman portrayed in Synecdoche, New York, Charlie Kaufman’s directorial debut. The film takes the desperately human postmodernism that characterized Kaufman’s scripts for Being John Malkovich and Eternal Sunshine of the Spotless Mind and expands it into an epic exploration of the exquisite misery of human existence. It’s one of the most ambitious comedies of all time, to the point where it feels unfair to reduce it to one genre. Synecdoche, New York isn’t just a film about the biggest things imaginable (art, love, family, mankind’s search for meaning in a random and insane world); it’s a film about everything. The immense gravity Hoffman brings to his role keeps the entire movie from spinning off into the ether, no matter how surreal it becomes.

5. The 25th Hour (2002)

In The 25th Hour, Spike Lee’s hyperreal meditation on post-9/11 New York, Hoffman, Barry Pepper, and Edward Norton play childhood friends who have held onto that bond even as adulthood has pulled them in such different directions, it’s doubtful they would be friends if they’d met as adults. The film follows this trio of friends in the uncertain day and night before Norton’s character has to turn himself in for a long prison sentence. Hoffman is cast against type as the most bookish of the trio, a shy teacher with a crush on a 17-year-old student played by Anna Paquin, who shows up unexpectedly during the trio’s night of debauchery in ways that both excite and terrify Hoffman’s character. In The 25th Hour, the city is electric with excitement, and Hoffman’s performance — at once wonderfully life-size yet bursting with unrequited longing — adds to this sense that the city itself is alive, a creature with a will of its own.

4. The Big Lebowski (1998)

In a perfect world, Hoffman would have become a ubiquitous repertory player in the Coen Brothers’ films, joining folks like George Clooney, Steve Buscemi, and John Turturro in playing a series of scamps, ne’er-do-wells, and colorful characters. Alas, Hoffman’s corner of the Coen Brothers’ sprawling cinematic universe is a small one, but as with so many of Hoffman’s attention-grabbing turns in seminal films of the 1990s, there is an inverse relationship between his limited time onscreen and the impact he makes. Acting opposite Jeff Bridges in his career-defining role as shaggily heroic 1960s casualty the Dude, Hoffman is exquisitely smarmy and unctuous as the glad-handing flunky of the wheelchair-bound crank known as the Big Lewbowski, whose life ends up overlapping with the Dude’s in hilarious and unexpected ways. Hoffman plays the character as a man so meek, he’d apologize to his own shadow for getting in its way.

3. Boogie Nights (1997)

Hoffman followed up his scene-stealing bit part in Hard Eight with an even more remarkable scene-stealing supporting role in Boogie Nights, P.T. Anderson’s brilliant, empathetic exploration of the bruised hearts and overheated loins of the late 1970s/early 1980s SoCal porn scene. You’d have to go back to American Graffiti or Dazed and Confused to find a movie that gave as many career-making roles to future stars, but even in this esteemed company, Hoffman’s performance as Scotty, a gay crew member with a tragic lack of awareness about which clothes flatter his frame, stands out. With a lesser actor, Scotty could easily have come across as a homophobic caricature of a pathetic guy delusionally in love with someone he can never have (Mark Wahlberg), but Hoffman makes him wonderfully relatable, a sweet man with an impossible crush neither the movie nor Hoffman judge him for.

2. The Master (2012)

With his pale skin, striking red hair, and unconventionally compelling looks, Hoffman bears a distinct physical resemblance to L. Ron Hubbard, the controversial author of Battlefield Earth who also apparently unlocked the secrets of the universe and was willing to share them with acolytes of the Church of Scientology for a steep cost. So when Anderson was looking for an actor to play Lancaster Dodd, a larger-than-life author and philosopher overtly based on Hubbard, Hoffman’s casting was a no-brainer. Even someone as brilliant as Anderson at utilizing Hoffman’s gifts might not have realized, however, what explosive chemistry the actor would have with Joaquin Phoenix, who tackles the equally challenging but different role as the raging man-child Dodd takes on as sort of a protégé, surrogate child, and strange alter-ego. More importantly, however, Hoffman had the cult-leader charisma required to play a man so captivating in his magnetism that he was able to convince seemingly intelligent people to abandon their critical faculties and give themselves over to his fantasies of endless personal potential. Almost Famous might have given Hoffman a better role than The Master, but no role was bigger than the majestic con of a man he played here. Paul Thomas Anderson’s collaboration with Hoffman began with a small but significant part in Hard Eight, but the scope of their partnership grew in size until it required the largely anachronistic format of 70mm — used in massive epics throughout the 1950s and 1960s before falling out of favor — to contain its majesty.

1. Almost Famous (2000)

Phillip Seymour Hoffman is the big, bleeding heart of Almost Famous, Cameron Crowe’s semiautobiographical comedy about coming of age in the 1970s’ debauched rock-and-roll world. In perhaps his signature role, Hoffman plays legendary rock journalist Lester Bangs as a beacon of compassion disguised as an intimidating grouch, a philosopher in the shabby costume of a slob. Though Hoffman’s role is exceedingly brief, it’s tough to overestimate its importance to the film. Bangs doesn’t just offer crucial mentorship to Crowe’s doe-eyed surrogate at a time when he needs it most. No, the performance transcends the film itself (even a film as beloved as Almost Famous) so that Bangs, through Hoffman — or possibly Hoffman, through Bangs (when an actor and character fuse to this extent, it’s tough to separate them) — is sending out a timeless message of radical self-acceptance to anyone who needs it. In death, as in life, Hoffman belongs to us all, but he belongs to the misfits, outsiders, and oddballs he played so compellingly most of all.