When Philip Seymour Hoffman died of an accidental drug overdose on February 2, 2014 at age 46, it felt like a huge part of the past two decades of cinema had disappeared as well, as if all the wonderful characters he created were on some level buried with the man who played them. A shocked public experienced a profound double loss. They were mourning the Hoffman who took up such formidable real estate in many modern classics. But they were also mourning all the brilliant Hoffman performances to come, which were extinguished with Hoffman’s death.

It was shocking because of his private nature. He wasn’t a tabloid fixture or subject of gossip. He was an artist who lent the often ridiculous and ephemeral act of pretending to be other people an innate dignity. He wasn’t averse to big paychecks—he appeared in Mission: Impossible III and the Hunger Games films, and was Ben Stiller’s wacky sidekick in the radiantly mediocre Along Came Polly—but he seemed to approach every role with an utmost seriousness that seldom veered into pretension.

The red-headed scene-stealer (1991-1996)

1 Triple Bogey On A Par Five Hole 1991 2.5 Leap Of Faith 1992 3.5 My New Gun 1992 2 Scent Of A Woman 1992 3.5 My Boyfriend’s Back 1993 2.5 Money For Nothing 1993 3 When A Man Loves A Woman 1994 4 Nobody’s Fool 1994 2 The Getaway 1994 2.5 Twister 1996 4 Hard Eight 1996

Hoffman made a big impression in small roles in small movies early in his career, using his unique physicality—that shocking red hair, translucent skin, and giant-toddler body—to upstage the other actors around him, especially when the material he was in didn’t match his extraordinary talent. That happened often during the early years. Hoffman made his big-screen debut in 1991’s little-seen Triple Bogey On A Par Five Hole as an unsavory sort known only as “Klutch.” He doesn’t have much screen time, but he makes his present felt with his fingerless motorcycle gloves, sleeveless T-shirt, bandanna, and demonic cackle. Hoffman briefly livens up the proceedings; then Amos Poe’s pretentious riff on Citizen Kane and the ennui of the idle rich goes back to being deeply boring. In Stacy Cochran’s sly, largely forgotten comedy My New Gun, Hoffman, looking a little like Ralph Malph gone to seed, laughs with seemingly drug-induced glee at how much he loves an epic fucking rainstorm. He talks about vomiting blood, shows off a neck tattoo, then lurches offscreen in the rain, never to be seen again. Hoffman logs maybe a minute of screen time, but even in a movie as offbeat and clever as My New Gun, it’s hard not to wonder, “Who is that man, and why isn’t the movie just about him?”

Hoffman was one of those prematurely wizened types who appeared never to have been young. Even with shaggy hair and a prep-school uniform, Hoffman exudes a distinct worldliness as George Willis Jr., an oily child of privilege who tries to pressure an scholarship underdog Chris O’Donnell into not snitching on Willis’ equally caddish buddies in 1992’s Scent Of A Woman. Alternating between faux-innocence and oily pragmatism, Hoffman gives the character the wise-beyond-his-years caginess of a man who thinks he understands how the world works, even if that knowledge really only extends to knowing just how protected he is by his daddy’s wealth and privilege.

In Bob Balaban’s chipper, surprisingly clever horror comedy My Boyfriend’s Back, no one seems remotely surprised or concerned when the protagonist rises from the grave to take the girl of his dreams to the prom, including Hoffman’s Chuck Bronski, the sidekick of the school’s head jock (Matthew Fox). The young actor distinguishes himself in a surprisingly distinguished company of character actors that includes Edward Herrmann and Cloris Leachman, combining a caveman slouch and an unnerving glare combine to create an unworldly air. Even in a cast full of scene-stealers, Hoffman stood out. My Boyfriend’s Back wasn’t Hoffman’s only half-forgotten 1993 movie with a preposterously overqualified cast. The fact-based slice-of-life Money For Nothing pairs star John Cusack with a supporting cast including a young, mustachioed Hoffman as a disgruntled dock worker who puts the squeeze on Cusack’s protagonist Joey once he figures out that the money Joey keeps flashing wasn’t acquired through legal means. A cigarette dangling from his lips, a hat over his regrettable sheepdog hair, his voice a gravely working-class rasp, Hoffman plays a neighborhood guy who’s a little savvier than the people around him, albeit not in a way that necessary benefits him.

Sporting a dirty bandana and an eternal-summer wardrobe that makes him look a little like a pirate, a young Hoffman made up part of the ace supporting cast in 1993’s Leap Of Faith, playing part of the motley crew of hucksters that make it possible for a sham preacher played by Steve Martin to fleece the faithful. Leap Of Faith roars out of the gate. The camaraderie shared by Hoffman and other crew members is infectious, as is their reverence for their boss’ genius for canny manipulation. But the film eventually devolves into sentimental mush. As always, Hoffman makes the most of his tiny screen time, turning the character into a true believer in the life-affirming powers of fraud, though he’s a richly merited skeptic about religion, particularly when it takes the form of a circus sideshow.

In 1994, Hoffman turned up in another tiny but attention-grabbing role when he played Gary, a recovering alcoholic who strikes up an intense friendship in rehab with Meg Ryan’s self-destructive protagonist Alice Green in When A Man Loves A Woman. Once again, Hoffman isn’t onscreen for more than a few minutes, and has only a few lines, but it’s enough to establish him as a serious threat to Alice’s relationship with her husband Michael (Andy Garcia). The openness and vulnerability of Hoffman’s performance—all cornerstones of his work to come—makes it easy to see why Alice could be attracted to him, and why even a man as handsome and charming as Michael might be jealous of the emotional intimacy Gary shares with Alice, simply by understanding her addiction.

As a seriously pissed-off small-town cop in Robert Benton’s wonderful 1994 character study Nobody’s Fool, Hoffman doesn’t do much more than get knocked out with one punch by an old man. But it’s a testament to his ability to choose films enduring roles that the old man doing the punching was Paul Newman, and the film was one of the year’s most quietly charming sleepers. It wasn’t all prestige films opposite Paul Newman for the young actor, however. He also paid his dues playing sleazy henchmen types like vampire-pale scuzzbucket Frank Hansen in forgettable films like Roger Donaldson’s nasty-but-not-nasty-enough take on Jim Thompson’s The Getaway. Hoffman doesn’t make it past the first act, and he wears a mask during his most memorable scene, but at least he had the consolation of one of what became a series of memorable onscreen deaths. Hoffman lustily devours what little scenery isn’t destroyed by CGI tornadoes in the idiotic 1996 blockbuster Twister. Clad in WalMart finery, Hoffman’s storm-chasing madman Dusty laughs with orgasmic delight at the prospect of getting all up inside a dangerous, even deadly tornado. He’s a wacky slob of a cartoon rocker (hilariously introduced rocking out to a late-period acoustic Eric Clapton song) who gets high off the danger and camaraderie of chasing twisters, and possibly some less-organic mood-enhancers as well. It’s a big, goofy, unselfconscious performance of utter shamelessness that marks the last time Hoffman played a role that could just as easily have been filled by Pauly Shore.

In the bit roles that littered the early years of his career, Hoffman all but lunged for the camera with wild-eyed abandon. But he was brilliant and charismatic enough to ensure that enjoyment was both justly merited and shared by the audience. Take Hoffman’s first collaboration with Paul Thomas Anderson in 1996’s Hard Eight. Though billed only as “Young Craps Player,” he delivers the kind of performance that demands attention. Clad in an airbrushed T-shirt of horses prancing in front of lightning, a cigarette dangling from his mouth, his hair done up in a tragically 1990s mullet, Hoffman’s overly confident jackass makes the mistake of taunting Phillip Baker Hall’s Sydney with a manic, nonstop string of patter that combines age-based insults delivered in a sing-song rasp of some unknown Southern derivation with scat-like bursts of subverbal nonsense like “Shack a lack doody doo.” Sydney, impeccably put together and radiating old-school dignity, understandably looks at his vulgar, classless antagonizer like something foul-smelling he stepped on, but damned if the abrasive nonsense doesn’t fluster Sydney’s stone-faced façade just a little. Forget screen time or lead roles; in his youth, Hoffman didn’t even need for his characters to have names to make them memorable.

The best part of the best movies (1997-2005)

5 Boogie Nights 1997 3.5 Next Stop Wonderland 1998 1 Montana 1998 4.5 The Big Lebowski 1998 4 Happiness 1998 .5 Patch Adams 1998 4.5 The Talented Mr. Ripley 1999 4.5 Magnolia 1999 1.5 Flawless 1999 3.5 State And Main 2000 5 Almost Famous 2000 2 The Party’s Over 2001 4 Punch-Drunk Love 2002 3 Red Dragon 2002 4.5 Owning Mahowny 2002 4 Love Liza 2002 4.5 25th Hour 2002 3 Cold Mountain 2003 2 Along Came Polly 2004 3.5 Capote 2005

Hard Eight marked a turning point in Hoffman’s career, in part because it began a collaboration with fellow wunderkind Paul Thomas Anderson that led to Boogie Nights, Magnolia, Punch-Drunk Love, and The Master. He was still stuck in the realm of supporting roles, but the roles and the films mattered in a way his early dues-paying work never did. Cream rose to the top, and in the middle part of his career, Hoffman worked not just with Anderson repeatedly, but also the Coen brothers, Todd Solondz, Cameron Crowe, Anthony Minghella (twice), David Mamet, Spike Lee, and Bennett Miller (also twice).

Hoffman doesn’t appear onscreen until 40 minutes into Paul Thomas Anderson’s 1997 breakthrough Boogie Nights, and he doesn’t have as much screen time as the rest of the overstuffed cast. His gut squeezed into too-tight tops, his legs jammed into short-shorts so tight they must have cut off his circulation, Hoffman plays Scotty, a boom operator with a desperate crush on charismatic porn star Dirk Diggler (Mark Wahlberg) so intense that he devolves into a state of fluttering semi-incoherence whenever he’s around his object of affection. Scotty is doomed never to fit in with the rest of the guys, as much due to his nervous, geeky disposition as his sexuality. But there’s nothing remotely mocking or condescending about Hoffman’s performance, which invites audiences to feel his pain and yearning rather than laugh at it. Hoffman once again plays a man without barriers or defenses, a sweetheart who is all vulnerability, openness, and yearning for acceptance. He tiptoes around his obsession for rightful fear of being hurt in a way he won’t be able to recover from. His writhing self-hatred as he sits in a car by himself, during the New Year’s Eve party that marks the beginning of the end for the high times, is as raw and electrifying as anything in Anderson’s towering masterpiece.

One of the unfortunate aspects of Hoffman’s too-brief career is that he didn’t get to play more wholly comic roles, because in movies like 1998’s Next Stop Wonderland, he’s hilarious playing Sean, a shaggy hippie activist who tries to use his crunchy lefty ideals to mask a toxic self-regard that has poisoned his relationship with a directionless nurse played by Hope Davis. Hoffman was brilliant at playing both extremes of self-esteem: Few could match his gift for playing quiveringly vulnerable sad-sacks, but he was also brilliant at playing arrogant men like Sean, in part because he understood that such men are almost invariably covering up for deep-seated insecurities. The low-key romantic comedy is entertaining throughout. It’s purposefully slight, but it’s never more winning than during Hoffman’s few scenes.

Throughout the mid- to late 1990s, video-store shelves were filled with dreadful Quentin Tarantino knockoffs peddling a tediously derivative blend of tough-guy philosophizing, twisty plotting, and underworld melodrama. Even Hoffman wasn’t immune to the strange siren song of this regrettable subgenre, and he delivered one of his most forgettable performances as a Machiavellian underworld schemer in the dreadful, inessential 1998 crime drama Montana. He had a much more memorable role as Brandt, a hilarious unctuous flunky to wheelchair-bound crank and pretend millionaire Jeffrey Lebowksi in the Coen brothers’ brilliant 1998 cult classic The Big Lebowski. As a 1960s-burnout-turned-unlikely shamus, Bridges plays the embodiment of slacker zen; he doesn’t seem to be acting, just existing, channeling some Dude-like space deep within his soul. Hoffman, in sharp contrast, is all fluttering artificiality: His fake laughter and fake formality are designed to create the illusion that the Lebowski household is a sane, rational, respectable, and morally sound place, rather than a madhouse spinning out of control, overseen by a petty tyrant pretending to be something he isn’t. The Big Lebowski belongs to Bridges, of course. It’s the most iconic role in his remarkable career. But as in Boogie Nights the year before, Hoffman once again proves to be one of the best parts in a great ensemble.

In 1998’s Happiness, Todd Solondz’s controversial exploration of the brutal folly of all human endeavor, Hoffman plays Allen, a wage slave with the cruel haircut and fashion sense of a nerdy 10-year-old, a speaking voice that suggests a mouthful of peanut butter, and the clammy, almost unbearable air of a man desperately trying to crawl out of his skin. Allen is a crank-caller and sexual harasser who leads a life of sad grey desperation during the day. Then at night, he engages in much louder desperation by calling strangers and his intrigued hipster author neighbor Helen Jordan (Lara Flynn Boyle) and unloads his grotesque sexual fantasies on them while masturbating. Like so many of Hoffman’s outcasts, he’s ruled by his compulsions. Hoffman grunts more than he breathes; everything seems difficult for him. He forever seems on the verge of an asthma attack, a panic attack, or, more disturbingly given his predilections, a messy orgasm. But within this framework of brutal awkwardness and painful dysfunction are flashes of tenderness in the character’s relationship with a depressed neighbor (Camryn Manheim) who may be even more disturbed and in need of connection than Allen. Happiness spends more than two hours staring deep into the void, and Solondz could take comfort in the knowledge that actors like Hoffman would not blink in the face of darkness.

1998 was a breakthrough year for Hoffman, but it also saw the release of two of his worst films: Montana and Patch Adams, a rightly mocked exercise in mawkish sentimentality. Patch Adams cast Hoffman as Mitch Roman, the protagonist’s college roommate and early antagonist, an uptight teacher’s pet in school-picture outfits who views Adams’ antics with justly merited irritation. Hoffman lends a welcome prickliness to his early scenes sparring with Robin Williams’ Adams. Then he disappears for an hour and returns as a convert to Adams’ sappy brand of uplift. He gazes adoringly at Adams, eyes dewy with rapt appreciation as the doctor-clown works his magic. This radical shift from aggravation to worshipful dedication marked one of the few times in Hoffman’s career he was wholly unconvincing.

As Freddie Miles, debauched son of privilege, Phillip Seymour Hoffman zooms onto an Italian street in a sexy convertible and roars, “Don’t you want to fuck every woman you see just once?” in Anthony Minghella’s electrifying 1999 psychological thriller The Talented Mr. Ripley. In a performance rich in mocking, malevolent humor, Hoffman plays Freddie as an unabashed hedonist whose apparent recklessness does not keep him from being the only person in the film who immediately sizes up Matt Damon’s Tom Ripley as a fraud who has what Freddie wants—the attention of Jude Law’s beautiful playboy Dickie Greenleaf—and wants what Freddie has, in his more stable, longterm friendship with Dickie. From the moment Freddie locks eyes with nervous, overmatched Tom Ripley, there’s an electrifying tension as the men jockey for position in a sexually charged conflict that can only be resolved with one party exiting not only the situation, but this earthly plane. Hoffman’s brilliant, bored, but razor-sharp dandy bullies Ripley with such sinister wit that he almost inspires sympathy for a murderous con artist. But in just one of the film’s exquisitely wrought tragedies, Freddie’s savvy and insight aren’t enough to save him.

If Freddie Miles is the voice of debauched experience, Phil Parma, Hoffman’s character in Magnolia, released the same year, is his attitudinal antithesis. He’s an earnest nurse who sits by towering patriarch Earl Partridge (Jason Robards) as he messily unpacks a lifetime of regrets on his deathbed. Hoffman once again gives a performance that’s all raw nerves and aching vulnerability. He plays Parma as an angel of mercy, blessed with a divine light that almost makes it seem possible that he’s capable of saving Earl, or at least offering him some manner of absolution. Playing a man with only goodness and longing in his soul, Hoffman makes decency seem profound, and kindness endlessly compelling. At the time, the scenes between Hoffman and Robards felt almost unbearably intimate; now that both men are dead, they’re almost unbearably sad.

On paper, at least, 1999’s Flawless must have looked liable to keep Hoffman’s winning streak going strong. It cast Hoffman in the challenging role of a drag-queen singing teacher opposite Robert De Niro as an angry, hateful, homophobic retired cop who can barely communicate after a stroke. The pairing of two of the greatest actors of all time radiates promise, but Joel Schumacher pushes what should have been sensitive, measured material into the vulgar direction of a sleazy crime comedy pitting stereotypical drag queens with the requisite hearts of gold against a bunch of cartoonish bad guys. Seldom has a film in Hoffman’s filmography been so mistitled.

Hoffman tended toward extremes of human behavior, hurtling between intense, psychotic villains, tragic heroes, mercurial geniuses, and outcasts just barely surviving on society’s fringes. So it’s refreshing to see Hoffman play a sweet-natured, likable romantic lead in David Mamet’s sly 2000 satire State And Main. Hoffman plays Joseph Turner White, an adorably bookish playwright who comes to a New England town to work on the film adaptation of one of his plays and receives a crash course in the movie world’s ability to corrupt everything it touches, himself included. White begins the film full of misplaced idealism, and ends it older, wiser, and violently disabused of his illusions about the purity of art in the face of the inexorable demands of commerce. Mamet’s quick-witted, eminently quotable take on the duplicity of show-business folk is almost too clever for its own good, but Hoffman’s tender and disarming performance, and his surprisingly strong chemistry with love interest Rebecca Pidgeon, at least lends the illusion that the film is about people worth caring about, rather than Mamet’s own delight in his effervescent wit.

In 2000, Cameron Crowe paid Hoffman the honor of casting him as his mentor, —and a popular candidate for the greatest rock writer of all time—Lester Bangs in the semi-autobiographical Almost Famous. Hoffman plays Bangs as a chain-smoking, righteously contrarian guru of the uncool, and an unlikely paragon of hard-won underdog wisdom. Hoffman’s dialogue has the ring of poetry. He’s the mentor everyone wants and nobody gets, and Hoffman delivers a performance that matches Crowe’s famous love and generosity toward his inveterately flawed dreamers.

Hoffman begins the curious 2001 political documentary The Party’s Over with the line, “I decided to host this documentary because I felt ill-informed.” The words and ideas that follow strongly support his contention. Pot-bellied, shaggy, and baseball-capped, Hoffman spends the documentary awkwardly, earnestly shoving microphones in people’s faces and asking questions only slightly more insightful and specific than, “So, what’s the deal with politics, huh? It all seems pretty crazy!” Hoffman comes across like a Michael Moore who never contests what he’s being told, or alternately, an Ali G who politely nods while ancient politicians prattle on instead of cracking jokes. The idea, beyond informing Hoffman about the issues of the day, is to take a litmus test of where the country was politically and culturally on the dawn of the 2000 election. It’s mostly watchable for the rare, poignant glimpse it provides into an actor who was never accused of playing himself because he had no real public persona.

Following the suicide of his wife, Liza, Hoffman’s Wilson Joel falls apart in the heartbreaking 2002 character study Love Liza. He takes to huffing gas in an attempt to distort a reality he cannot confront sober or lucid. That habit leads to a sense of fraternity with his community’s aggregation of remote-control-loving weirdoes, who are eager to add someone new to their group, even if it’s a suicidally depressed man who uses their hobby largely as a cover for his addiction. Hoffman delivers a performance devoid of vanity of self-consciousness. He’s a wounded, raw nerve who finds it difficult to make small talk or keep up appearances; he’s lost in grief, lost in depression, and just plain lost.

Hoffman wasn’t afforded many opportunities to play unremarkable characters, but he’s quietly impressive in 2002’s 25th Hour as Jacob Elinsky, a meek teacher who comes along with hyper-aggressive Frank Slaughtery (Barry Pepper) on one long, last night of the soul before their buddy Monty (Ed Norton) is scheduled to begin a seven-year sentence for dealing drugs. But even this seemingly unassuming man has secrets of his own, in the form of a crush on student Mary D’Annunzio (Anna Paquin) who isn’t shy about flaunting her adolescent sexuality—or coming on to a teacher who should know better. Hoffman isn’t the focus of 25th Hour, but he is the moral center of Spike Lee’s haunting elegy for post-9/11 Manhattan.

Bret Ratner’s 2002 Thomas Harris adaptation Red Dragon is the least, and least-memorable, of the four films chronicling the cannibalistic misadventures of lovable scamp Hannibal Lecter. But as Freddie Lounds, sleazy tabloid journalist, Hoffman stood front and center in its most memorable scenes. Red Dragon probably won’t be on anyone other than Brett Ratner’s list of the 10 greatest Philip Seymour Hoffman performances, but not every film affords an actor an opportunity to exit the story as a melting corpse in a flaming wheelchair. Even in his most commercial, least-essential films, Hoffman had a way of making his mark.

Much better, though it’s one of Hoffman’s lesser-known films, is Richard Kwietniowski’s masterful 2003 character study Owning Mahowny. Hoffman plays Dan Mahowny, a real-life bank employee who embezzled more than $10 million in early-1980s Toronto to feed an insatiable gambling addiction. Hoffman sports a deeply unflattering mustache and a series of cheap suits as a man who uses his own beige banality to mask a feverish compulsion for self-destruction. Hoffman is equally brilliant playing the three distinct sides of Mahowny: the public self who’s efficient in his professional life to the point of being boring, the personal side who sneaks away from his entirely too accommodating girlfriend to spend bleary nights gambling away a fortune with a stone-faced intensity that earns him the nickname “The Iceman,” and the secret self who trembles with dread over the consequences should his massive theft be discovered. Hoffman does a masterful job revealing the hairline cracks in Mahowny’s carefully cultivated facade.

In 2003, Hoffman re-teamed with Minghella to play another Falstaffian figure, this time Reverend Veasey, a man of faith more obsessed with the pleasures of the flesh than the salvation of the spirit. He’s an incorrigible ne’er-do-well who briefly brightens up Minghella’s elephantine adaptation of Cold Mountain with his raucous good humor and unrepentant lust for the ungodly life, only to commit a sin all too common for Hoffman during this era: not being onscreen nearly long enough. Similarly, the problem with casting an actor of Hoffman’s caliber as the protagonist’s best friend in a forgettable, slight romantic comedy is that it makes every moment he’s not onscreen feel like a wasted opportunity. That’s true of the 2004 surprise hit Along Came Polly. The film cast Hoffman as Sandy Lyle, a former child actor stuck emotionally at the age of his greatest fame, somewhere between 11 and 12. Hoffman throws himself into the role of a narcissistic man-child overflowing with wildly unmerited self-esteem. The cockiness that competed with vulnerability as Hoffman's dominant mode becomes hilarious here; there is more joy and humor in a minute of Lyle, his big beer belly squeezed into a too-tight T-shirt, screaming braggadocio trash-talk as he hurls the basketball somewhere in the general area of a basket than there is in the rest of the entire misbegotten movie.

The role of Truman Capote—witty bon vivant and unlikely chronicler of the Midwest’s murderous underbelly—was not the best in Hoffman’s extraordinary career. It was, however, the most Oscar-friendly. So it’s not surprising that Hoffman picked up his only Oscar as the lead character in Bennett Miller’s 2005 film Capote, a handsomely mounted, slightly remote and overcooked period drama about Capote traveling to Kansas City with friend Harper Lee (Catherine Keener) to research and write about the brutal murders of the Clutter family at the hands of Perry Smith (Clifton Collins Jr.) and Dick Hickock (Mark Pellegrino), the subject of Capote’s In Cold Blood. Hoffman plays Capote as a man of ruthless pragmatism who uses his extraordinary guile and understanding of the complexity of the human nature to ingratiate his way into the story of a lifetime. Hoffman is quietly harrowing and surprisingly understated as a man who posits himself as an empathetic friend to the downtrodden, but whose only real allegiance is to his own professional desires. His performance makes it easy to get seduced by the giddy ebullience of Capote’s public persona before becoming deeply unnerved by his inner heartlessness.

A master emerges (2005-2014)

3.5 Strangers With Candy 2005 3.5 Mission: Impossible III 2006 4 The Savages 2007 3.5 Charlie Wilson’s War 2007 4 Before The Devil Knows You’re Dead 2007 4 Doubt 2008 4.5 Synecdoche, New York 2008 2.5 Pirate Radio 2009 4.5 Mary And Max 2009 3.5 The Invention Of Lying 2009 3.5 Jack Goes boating 2010 3 The Ides Of March 2011 3.5 Moneyball 2011 3 A Late Quartet 2012 5 The Master 2012 3.5 The Hunger Games: Catching Fire 2013 3.5 A Most Wanted Man 2014 2.5 God’s Pocket 2014 4 The Hunger Games: Mockingjay—Part 1 2014

Once Hoffman picked up that Best Actor Oscar, he didn’t mess around with many bit parts: He tended to commit to invariably challenging roles with his whole soul. But he made an exception for the 2006 feature-film adaptation of Amy Sedaris’ cult sensation Strangers With Candy. Hoffman is one of a slew of famous new faces lending a blast of star power to the good-enough cinematic spin on the irreverent spoof of after-school specials. Strangers With Candy obviously did not need an actor of Hoffman’s stature for the exceedingly minor role of a school-board member, but he’s able to make his character’s feverish jealousy funny and sad. Even at his silliest, Hoffman had a gift for melancholy.

J.J. Abrams’ 2006 hit Mission: Impossible III is never less than solid, but it grows exponentially better whenever Hoffman is onscreen as bad guy Owen Davian. Mission: Impossible III gives Hoffman one of his all-time great introductions: He opens the film by threatening to murder Ethan Hunt’s wife, and even though he’s offscreen for most of the film’s first hour, the threat is ever-present. Hunt (Tom Cruise) is defined by his invulnerability, his genius for pulling off impossible missions, as it were, but he never seems more vulnerable or human than when Davian is directing the full force of his concentrated evil in Hunt’s direction. As Davian, Hoffman is so sneeringly malevolent and convinced of his own indestructibility that even when Hunt and his team of world-class spies have him in captivity aboard a plane, Davian never stops making shockingly convincing threats to murder Hunt and everyone close to him. He’s a terrifying force of evil who throws Hunt around like a rag doll. His ferocity in his few scenes can’t help but make the rest of the film seem like a quaint little travelogue by comparison.

As an actor, Hoffman was intimately familiar with the geography of sadness and solitude. It was terrain he knew well, and he brought that understanding of misery to the role of Jon Savage, a professor at a personal and professional crossroads in Tamara Jenkins’ wonderful, meticulously composed, bone-dry 2007 film The Savages. Hoffman brings to the role the exhausted body language of someone who is utterly exhausted and overwhelmed by stress and anxiety, but cannot concede defeat, no matter how badly he might want to. His potbelly pressed into a series of shapeless T-shirts, his eyes sad and lost, Hoffman plays a man forced to care for a dementia-ridden father (Philip Bosco), who was never particularly interested in caring for Jon or his sister Wendy (Laura Linney) when they were kids, and isn’t too pleased about their reunion as adults. The Savages is a brutally funny, boldly unsentimental exploration of the complicated and often painful emotions a parent’s mortality evokes, particularly when the relationship is as dark and emotionally fraught as the one Jon and Wendy share with a man intent on kicking and screaming his way to the grave. Hoffman plays Jon as a man who puts all his energy into just barely holding it together. Over the course of the film, even that proves too much, and more than once, Hoffman weeps openly, as if to finally concede, if only to himself, just how devastated he is by everything around him.

Aaron Sorkin writes two kinds of roles: juicy ones and non-speaking parts. He wrote a particularly juicy role for Hoffman in 2007’s Charlie Wilson’s War: Hoffman plays Gust Avrakotos, a spy who uses his bluntness and the battering-ram force of his personality to plow past social niceties to get what he wants. He’s a gravel-voiced poet of profanity who finds a kindred spirit in Tom Hanks’ Charlie Wilson, a hard-drinking, hard-living playboy congressman who finds meaning when he decides to aid the Afghan Mujahideen in their righteous struggle against their Soviet oppressors. Wilson is all honey-dripping charm and guile, while the defiantly vulgar, working-class Avrakotos is a blunt instrument of a man. For a solid decade, these antithetical figures played a huge role in helping win a secret war against communist oppression they’re both savvy enough to realize could, and probably would, have blowback the likes of which more cautious souls could never anticipate. Hoffman’s flashy, Oscar-nominated performance brings together two types he specialized in over the course of his career: the profane, street-smart tough guy who’s a whole lot sharper than he looks, and the world-conquering innate genius who’s the best at what he does, and has the ego and bravado that come with that mastery.

Hoffman could be a gladiatorial actor, a master of the form whose most memorable performances found him bending other actors to his will. His cold-blooded, calculating would-be mastermind Andy has a much easier time dominating Hank (Ethan Hawke) in Sidney Lumet’s brutal 2007 thriller Before The Devil Knows You’re Dead. But then, Hank is everybody’s patsy. The film found Hoffman playing what what had become a recurring type in his career: a man of ambition who looks put-together from the outside, but is dramatically falling apart on the inside. One Hoffman monologue aimed at a drug dealer explains how on an accountant’s ledger page, everything has to add up and make sense, but that in his own life, nothing does. It’s exactly the kind of on-the-nose, spelling-out-subtext scene that should ring melodramatic, and might if Hoffman didn’t turn it into the heartbreaking confessional of a man who can only fully reveal himself to someone who does not care whether his client lives or dies.

In Doubt, John Patrick Shanley’s 2008 adaptation of his own Pulitzer- and Tony-winning play, Hoffman plays Father Brendan Flynn, a charismatic dandy of a Kennedy-era priest who sweeps into a tradition-bound Catholic church and school and immediately makes a powerful enemy in Sister Aloysius Beauvier (Meryl Streep), the school’s dour principal. Hoffman plays Flynn as a portent of the kind of sweeping social change that terrifies Aloysius, who in turn sees in him all of the shadowy ills of the corrupt modern world. It is a performance rich in ambiguity, turning on the question of whether Flynn had a sexually inappropriate relationship with a student. Part of the genius of Hoffman’s performance—beyond his ability to go toe-to-toe with Streep at her most ferocious and larger-than-life—is that the film ends with that mystery fundamentally intact. Hoffman’s brilliantly measured performance doesn’t tip its hand one way or the other; it’s entirely possible that the character is a dangerous predator grooming a victim with kindness and compassion. But it’s just as likely that he’s being persecuted because he’s effete, progressive, and has personal affectations the prickly Aloysius finds offensive, like taking three lumps of sugar with his coffee, and keeping his fingernails long.

Charlie Kaufman’s 2008 directorial debut, Synecdoche, New York, would be unbearably sad if it weren’t so consistently hilarious. In one of the heaviest and most demanding roles in a life full of them, Hoffman plays Caden Cotard, an ambitious theatrical director who begins the film convinced the decaying mass of meat and bones he reluctantly calls his body will give out on him any day. He only deteriorates, psychologically and physically, from there. Caden is a stoop-shouldered man of constant sorrow who receives a MacArthur grant and sets out to create a theater piece so massive and experimental that it resembles a never-ending nightmare from which Caden, his audience, and his collaborators can never awake. For Caden, being alive means suffering, and letting the people he loves float away from him until he’s ultimately alone with his loneliness and his unrealizable ambition. He becomes the perpetually failing god of an insane, unmanageable world. He wants to leave great art in his wake, but leaves behind only emotional devastation. Synecdoche, New York is filled with far-out science-fiction and absurdist conceits, like a house that is forever on fire, and a play that takes decades to germinate and rehearse, and doesn’t really have an audience in mind. But Hoffman and an amazing cast play the material completely straight, as if it were a docudrama, not a Kafka-esque exploration of the horrors of life.

Hoffman contributed a rare cameo to 2009’s The Invention Of Lying, the bleakly comic tale of an alternate universe where lying doesn’t exist and everyone is brutally honest. As Jim The Bartender, Hoffman is only onscreen for a few minutes, but he gets a memorable chance to act opposite Louis CK and co-writer/co-director/star Ricky Gervais as Gervais’ loser-turned-messiah tries out the concept of lying on two guileless souls programmed to believe everything he says, no matter how far-fetched.

In his only lead performance as a voiceover actor, Hoffman brings a tremblingly sincere soul to the part of Max Jerry Horovitz, a melancholy, older Jewish man with Asperger’s who strikes up an unlikely pen-pal friendship with an Australian girl in the brilliant, sadly overlooked 2009 Australian stop-motion animated film Mary And Max, which premièred at Sundance, but wasn’t able to secure an American theatrical release. In collaboration with writer-director Adam Elliot and a team of stop-motion animators for whom the project is clearly a labor of love, Hoffman created an unforgettable character, extreme in his habits and obsessions, yet relatable in his yearning for connection and meaning.

In 2009, a shaggy, hirsute Hoffman played “The Count,” the sole American DJ on a wet, wild British outlaw radio station in Richard Curtis’ disappointing ensemble period comedy Pirate Radio (released in the U.K. as The Boat That Rocked). Hoffman delivers a larger-than life performance, playing the ex-pat DJ as a rock ’n’ roll true-believer, a shaggy, rambling cross between a less-cynical Lester Bangs and a more motivated version of The Big Lebowski’s The Dude. Pirate Radio’s mindless deification of the spirit of rock ’n’ roll is self-congratulatory hokum, but Hoffman’s performance as a man who understands how ridiculous and regressive rock can be, yet loves it unconditionally all the same, intermittently gives it an otherwise-unearned ring of truth.

Hoffman made what turned out to be both his directorial debut and his swan song with 2010’s Jack Goes Boating, an intimate working-class romantic comedy-drama that let Hoffman make his version of Marty. Hoffman brings a lumbering sweetness to the title role of Jack, a good-natured limo driver who’s made it to middle age without much romantic companionship. That promises to change when his best friend Clyde (John Ortiz) sets him up with Connie (Amy Ryan), a damaged, emotionally delicate woman desperately in need of the kindness and compassion her good-naturedly oafish new suitor offers. Hoffman’s elegantly understated direction doesn’t attempt to hide the film’s origins as a stage play. This is an actor’s showcase, pure and simple, but it’s enormously effective on that level. Hoffman and Ryan are heartbreaking as a man without defenses and a woman learning to let hers down in order to let love in.

Hoffman embodies a fascinating combination of battered idealism—his character believes in loyalty, if nothing else—and weary pragmatism as Paul Zara, a veteran campaign strategist in George Clooney’s slick 2011 political drama The Ides Of March, an ambitious potboiler about the political corruption of a young hotshot campaign worker played by Ryan Gosling. Hoffman brings instant authority to the role of a perpetually dyspeptic old pro at the helm of a presidential campaign amid a major moral crisis, playing the character as a battle-scarred warrior who can be outmatched and outplayed, but never conclusively destroyed. In his wonderful final scene, Hoffman uses something as simple as the way he holds his hands while smoking a cigarette to convey his character’s resilience and fundamental good humor. Hoffman’s cavalier body language alone conveys that he’s already well on his way to being able to laugh about the brutal hits he’s taken over the course of the film, because the only other option would be to be destroyed by them.

Hoffman reunited with Capote director Bennett Miller for the small but key role of Art Howe, the curmudgeonly manager of the Oakland A’s, in the sports-statistics drama Moneyball. Like Capote, they’re both dramas that cast Hoffman as real people in stories ripped from real life, but the characters themselves couldn’t be more dissimilar. Hoffman’s Capote was a social butterfly intoxicated with his own words, while Howe seems like the sort of old-school manager who tries to use as few words as humanly possible. It’s initially a little jarring seeing Hoffman with a buzz-cut, squeezed into a Major League Baseball uniform, but Hoffman is authentic and convincing as always, playing Howe less as a fool than a traditionalist who’s understandably skeptical of numbers-pushing Billy Beane (Brad Pitt) and his sidekick Peter (Jonah Hill). When Beane pushes him, despite Howe getting the A’s to the playoffs on a tiny budget just a year earlier, Howe pushes right back, and understandably so. It’s Beane’s story, but his conflict with Howe feels like a battle between equals, thanks to the quiet forcefulness Hoffman brings to the role.

A Late Quartet more or less lives up to the tasteful tedium of its title and premise, about a 25th-anniversary concert for a prominent string quartet that’s complicated by the leader (Christopher Walken) deciding to retire after the concert due to a recently diagnosed case of Parkinson’s disease. Other soap-opera complications ensue. A hard-driving, perfectionist quartet member played by Mark Ivanir threatens to disrupt the delicate alchemy of the group by having an affair with the hot-blooded daughter of married quartet members Juliette (Catherine Keener) and Robert (Hoffman). Robert, in turn, acts out his frustrations by having an extramarital affair of his own. A Late Quartet is so subdued and restrained that even a world-class ham like Walken gives a borderline-sleepy performance. But Hoffman finds the warm, scruffy, beating heart in this often-stuffy film, playing a kind man who discovers too late that his reward for waiting his turn and being a good team player for 25 years as the quartet’s second violinist has only earned him the opportunity to go on playing the good team player indefinitely.

When it was announced that Paul Thomas Anderson would be making a movie loosely based on Scientology and its enigmatic leader L. Ron Hubbard, rumors flew that the film would be a slashing and vicious satire. But anyone who expected a hatchet job on the eccentric author and philosopher misunderstood the empathetic nature of Anderson and Hoffman’s collaboration. Hoffman makes Lancaster Dodd, the Hubbard surrogate of 2012’s The Master, the best and worst kind of fabulist. He’s so gifted at spinning untruths that he gets himself to believe his lies. He’s all guile and control, a bon vivant who sees in deeply disturbed war veteran Freddie Quell (Joaquin Phoenix) a reflection of the animalistic man he can never allow himself to be, a rampaging id who drinks, fucks, curses, and leads a life as feral as Dodd’s is controlled. Underneath Dodd’s arrogance lies a vulnerability and light he allows the twisted-up Freddie to see as a way of bringing him closer, knowing that the relationship between these two impossible men could only end in heartbreak. Dodd emerges as a loving and chiding father-figure to Freddie, who desperately needs guidance and love, no matter the source. Shot in gorgeous, intimate 65mm, The Master is on some level a tragic love story about two men who need each other, yet cannot convey that devotion in healthy ways. Hoffman is never more powerful spinning seductive lies than in a final sequence where the perpetually tormented Dodd—who speaks with absolute authority about the nature of the universe, yet sees his doubt, anger and confusion reflected in Freddie’s gaze—seduces Freddie one last time with pulpy tales of their past adventures, even as he betrays him.

As Plutarch Heavensbee, the Head Gamesmaker in the second entry of the hit young-adult dystopia series, The Hunger Games: Catching Fire, Hoffman initially appears to represent the banality of evil. He’s a realpolitik Henry Kissinger to Donald Sutherland’s President Snow, all oily menace and sinister, cold-blooded calculation. But it turns out Heavensbee is playing a much bigger, more dangerous game than he initially lets on, and his character’s arc unfolds over the course of the next set of sequels.

By the time the John le Carré adaptation A Most Wanted Man hit theaters early in 2014, Hoffman had died, which lent an additional heaviness to a film that was already awfully grim. Hoffman brings a deep sense of world-weariness and an only occasionally distracting German accent to the role of counterterrorism expert Gunter Bachman. Bachman is another of Hoffman’s lost men, a lonely, struggling alcoholic who has learned from experience not to put too much faith in other people. That serves him well as he plays an elaborate chess match aimed at capturing and turning an ostensibly moderate Muslim professor he suspects of funneling money to terrorists. The dry wit Hoffman brings to the role lends the slightest hint of levity to a film that desperately needs it, and his performance reaches its apex in a final sequence that redeems an often cold and detached film. Hoffman plays a man running out of tomorrows, and the ending gains an added power from the queasy recognition that the brilliant actor playing a man chasing his endgame had already passed his.

Like A Most Wanted Man, John Slattery’s God’s Pocket is grim even by Hoffman’s standards. He plays a low-level criminal whose life is turned upside down when a killing at a construction site ricochets through a close-knit lower-class neighborhood. God’s Pocket overdoses on local color and Sundance-fed indie-film clichés, but the film improves as it goes along, as does Hoffman’s performance as his previously stable character loses his grasp on his life, and his grubby little empire and his defenses are blown apart by life’s random cruelty.

Hoffman returned as Plutarch Heavensbee in The Hunger Games: Mockingjay—Part 1, but this time his role is much more central, as Heavensbee uses Jennifer Lawrence’s Katniss Everdeen as the personification of a rebellion against the corrupt establishment. Heavensbee is equal parts idealism and pragmatism as a man who understands that winning the hearts and minds of a dystopian world is at least as much show-business as politics. Considering the serious, often dour nature of the films Hoffman made and the roles he played, it’s appropriate that he ended his career playing a man for whom putting on a good, convincing show is literally a matter of life and death.

Hoffman was an artist who didn’t play roles so much as inhabit them. Throughout his all-too-brief career in film, theater, and occasionally, television, Hoffman wrestled with the hard truths of human existence in all its richness, beauty, and contradictions. And though apart from the fourth Hunger Games, we’ll never see another performance from Hoffman, we can live forever in the bottomless depths of his professional past.