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His death on Sunday was a tragedy, for his family and friends, and for countless moviegoers around the world, who were shocked and surprised and positively dazzled every time Hoffman showed up on screen, even if they couldn't tell you exactly what his name was.
Hoffman essayed a number of memorable roles that go above and beyond the 10 we wrestled with choosing for this list -- it was a hard roundup to compile, for a number of reasons. It's almost impossible to think of a cinematic landscape devoid of Hoffman's esoteric sensibilities and crackerjack choices.
Still, if there were 10 performances in Hoffman's career that were truly unforgettable and deserve to be revisited in the days and weeks ahead, while we all grapple with this senseless death and the loss of a true icon.
Gallery | Philip Seymour Hoffman's 10 Most Unforgettable Performances
- 10. 'Charlie Wilson's War' (Mike Nichols, 2007)
This is one of those examples of Philip Seymour Hoffman's performance being much, much better than the movie it's a part of. "Charlie Wilson's War," Mike Nichols's true-life war comedy, is about a covert operation led by a U.S. senator (Tom Hanks) who conspires with a C.I.A. operative (Hoffman) to arm and train the Afghan mujahedeen during the Soviet war in Afghanistan. Aaron Sorkin's script is smart and Nichols's direction occasionally snappy, but you can feel (violently) each time a punch is pulled, and the movie is a mess editorially (a 9/11-era "Dr. Strangelove" is watered down to accommodate a Hanks/Julia Roberts romantic comedy). Thankfully, none of this seems to impact the power of Hoffman's performance; as a tightly wound, foul-mouthed secret agent, he's the anti-James Bond, spending just as much time facing bureaucratic nonsense as he is trying to sway the war. Hoffman makes us understand how such a fiery loose cannon could get along so splendidly with Hanks's svelte politician; they shared a similar ideology and frustration with a "system." It's a testament to the transcendence of his performance (he was nominated for an Academy Award for Supporting Actor) that it was one of the things I immediately wanted to revisit upon learning of the actor's death.
- 9. 'Happiness' (Todd Solondz, 1998)
Hoffman had appeared in a number of memorable movies before Todd Solondz's genuinely unsettling and hilarious "Happiness"; just a few years before, he had turned in a wonderfully unhinged performance in the Steven Spielberg-produced blockbuster "Twister." But with "Happiness," he became an actor who you got your blood pumping just by showing up. He played a man who made obscene phone calls to a neighbor who he was in love with (Lara Flynn Boyle), only to be rejected and fall in love with another neighbor (Camryn Manheim), who, it's suggested, is an operating serial killer. Ah love. If you haven't seen Solondz's NC-17-rated comedy, it's well worth seeking out, although it should be noted, if the above description didn't make it keenly aware, that it's not for the faint of heart. Hoffman was able to imbibe a role that can charitably be described as a "creepy weirdo" with real heart and pathos. The fact that you can openly sympathize with his character is a testament to his insane abilities as an actor and the odd compassion of Solondz's script. Critics complained that the filmmaker was making fun of his warped characters; what Hoffman showcased was just how much Solondz identified with them. (For bonus fun, watch Solondz's alternate universe sequel, "Life During Wartime," in which Michael Kenneth Williams plays the Hoffman role.)
- 8. 'The Big Lebowski' (The Coen Brothers, 1998)
Hoffman's lone collaboration with the Coens came in the form of the filmmakers' gonzo detective story "The Big Lebowski" (at the time, an ill-received follow-up to their Oscar-winning "Fargo"). His role isn't the largest or the showiest, but as Brandt, the "real" Lebowski's assistant and the intermediary between that Lebowski and Jeff Bridges's The Dude, he brought an unforgettable energy to a relatively minor character. His biggest scene occurs when he is showing The Dude around Lebowski's lavish estate, unable to truly articulate why Lebowski has been awarded so many civic prizes and taking The Dude's asides with a grain of salt ("You never went to college!") Hoffman spent so much of his career playing emotionally damaged, psychologically tortured souls (like his paint fume-huffing tour de force in "Love Liza") that he ended up being something of an under-appreciated comedian. This is easily one of his funniest roles, one in which his raw skill is easily appreciable. He doesn't just handle the Coens' knotty, overly manicured dialogue, he makes it seem like he was coming up with it off the top of his head. As his character Brandt would say: "That's marvelous!"
- 7. 'Mission: Impossible III' (J.J. Abrams, 2006)
When people talk about the third installment in the Tom Cruise-led franchise, it's usually more to do with the movie's striking similarities to James Cameron's "True Lies" than with the film's actual merits (of which there are a handful). One of the biggest pluses of the J.J. Abrams-directed sequel is Hoffman's performance as the villain, a lugubrious arms dealer named Owen Davian, who is looking to get his hands on a mysterious device known as a "rabbit's foot." His character is unique in the sense that he's not a mustache-twirling bad guy, although he does get to chew a fair amount of scenery, especially in the moment where he threatens to murder Cruise's new bride (Michelle Monaghan); instead, he's a coolly collected middleman, between the real villains and the man who want to keep those villains in business. One of the most spellbinding moments in the entire franchise is when Cruise replaces Hoffman using a mask he's fashioned, which allows for Hoffman to play Cruise playing himself. It's subtle but utterly brilliant, and stands as a testament to the fact that even when he's having fun, he's still a force of nature.
- 6. 'Almost Famous' (Cameron Crowe, 2000)
By the end of his career (and life) Hoffman had played a number of real-life characters and, Capoteaside (more on that in a minute), his most lovable based-on-a-real-guy performance was in Crowe's sprawling autobiographical masterpiece, as uncompromising Rolling Stones rock writer Lester Bangs. He occupies a tiny sliver of screen time but, as always, his presence occupies large chunks of the movie when he never appears. He is the voice inside the head of the movie's main character and Crowe surrogate William Miller (played by Patrick Fugit) and the figure who sets the character off on a quest of professional discovery and personal growth. While the movie wasn't initially seen as a hit, like many films in the Hoffman canon, it has grown to become something of a cult phenomenon. Part of that connection with audiences has to do with the fact that it offers a degree of wish fulfillment, and in Hoffman's performance, you get an understanding of the passion, brilliance, and combativeness that made Bangs such a legendary writer and personality. Thanks to Hoffman, you can understand how he could be so inspiring.
- 5. 'The Talented Mr. Ripley' (Anthony Minghella, 1999)
The Mr. Ripley character, as written by Patricia Highsmith and brought to life (beautifully) by Matt Damon in Anthony Minghella's note-perfect adaptation, is a kind of murderous shape shifter -- fearfully insecure and able to blend in, with enough time and practice, to virtually any situation. After befriending a pretty playboy (Jude Law), Ripley starts to expand his social network, growing and changing like the titular creature from John Carpenter's "The Thing" (and just as deadly). Of a particular threat to Ripley is Hoffman's character, a socialite named Freddie Miles who is friends with Law's character and who is immediately suspicious of Ripley. There's also something slinky and velvety about Hoffman's performance that suggests that Miles is able to exist as a homosexual male in a way that Ripley is never able to (another part of the Ripley character that is endlessly fascinating). This obviously makes Miles a prime target, and is able to give Hoffman something that he's only had a handful of times during his career: a really, really great death scene. (Jim Henson's company, which gave Minghella some of his first professional jobs, handled the squishy special effects.) Hoffman is the closest thing that the movie has to a voice of reason, so you're rooting for him even while he remains inherently unlikable. Freddie Miles is also the only Hoffman character whose brains wind up dotting a ceramic bust.
- 4. 'Punch-Drunk Love' (Paul Thomas Anderson, 2002)
At the time, "Punch-Drunk Love" felt like an experimental, Adam Sandler-led one-off from Paul Thomas Anderson, who up until this point had been doing Scorsese-indebted, Altman-esque ensembles. But he retained one key aspect from those earlier films when making "Punch-Drunk Love": Philip Seymour Hoffman, who had appeared in every one of Anderson's features up until this point. You can understand why: Anderson and Hoffman make beautiful, beautiful music together. (His roles in "Hard Eight," "Boogie Nights," and "Magnolia" could all easily be on this list, but then it would be too Paul Thomas Anderson-y.) In "Punch-Drunk Love," Hoffman plays a Mormon sleaze-ball who runs a discount mattress store (he calls himself the Mattress King) as well as a small-time criminal enterprise as a pornographer and phone sex operator. Some of the movie's best sequences happen between Sandler and Hoffman: a confrontation over the phone (too profane to repeat here) and a physical confrontation that plays wordlessly and so, so hilariously. Hoffman brings his usual inhuman levels of intensity to a character who is largely comic, and the results are simply dynamite. The film, as a whole, needs to be reassessed, and maybe with Hoffman's passing, this will finally come to pass.
- 3. 'Capote' (Bennett Miller, 2005)
In Hoffman's sole Academy Award-winning performance, he portrayed Truman Capote, in the events leading up to his unparalleled true crime book "In Cold Blood." Hoffman avoided a number of pitfalls in his performance of such a well known (and highly documented) public figure -- he could have easily given into crass caricature or cartoonish over-acting. Instead, his Capote is carefully modulated and fully, emotionally articulate. As he gets drawn deeper into the crime that he is documenting, his bonds with the accused start to become uncomfortably blurry, and the movie takes on an even more oppressive, claustrophobically dreary mood. Hoffman, writer Dan Futterman, and director Bennett Miller were longtime friends, and you can tell that the three of them worked hard in not simply Xeroxing historical data but creating a three-dimensional character, one that you could believe in instead of simply giggle at. In a movie whose color palette is almost black-and-white, Hoffman strikes like a bolt of lightning, supercharging everything around him. (The fact that he also pulled this off while competing against "Infamous," another Capote movie with almost the exact same plot, with Toby Jones playing Capote, is even more incredible.) And, yes, his Capote voice is spot on.
- 2. 'Synecdoche, New York' (Charlie Kaufman, 2008)
One of Hoffman's very best performances is also one of his most under-seen, thanks to the fact that it's housed within writer-director Charlie Kaufman's house-of-mirrors comedic drama. In the film, Hoffman plays an independent theater director who, throughout the course of the film, recreatesManhattan inside a giant warehouse and populates it with lookalikes of characters from his actual life. While Kaufman's original screenplay was slightly more nimble, Hoffman brings a level of psychological complexity that could have easily been rendered two-dimensional had another actor assumed the role. There's a level of goofiness to his performance, as there should be, but there's also a crushing level of sadness that makes the somewhat oversized plotting more relatable, understandable, and emotional resonant. "Synecdoche, New York" is a difficult movie, full of heady twists and the kind of narrative loop-de-loops that defined Kaufman's screenplay work ("Eternal Sunshine of the Spotless Mind," "Being John Malkovich," "Adaptation"), but those who are willing to take the challenge, they'll be rewarded with one of Hoffman's most original, wholly surprising performances. The movie is a trip. Hoffman is, too.
- 1. 'The Master' (Paul Thomas Anderson, 2011)
This is it. It's the movie that we wanted to put on the second we heard about Hoffman's passing, if only to soak in his genius one last time. It's the movie that stands as a towering achievement and testament to Hoffman's abilities as an actor and a empathetic human being. It's a performance that could only be achieved by Hoffman. And, after three years, it's a performance that we're still boggled by. In Paul Thomas Anderson's film, Hoffman plays Lancaster Dodd (pictured above), a rough approximation of Scientology founder L. Ron Hubbard, who becomes enamored with a troubled young drunk (Joaquin Phoenix). There's a degree of embellishment required of Hoffman anytime he's playing a historical figure, whether its Truman Capote or Lester Bangs, but with "The Master" he was gifted with Anderson's restless imagination, which incorporated everything from literary allusions to old stories Jason Robards had told Anderson on the set of "Magnolia" (stories that Hoffman would undoubtedly cotton to).
There's obviously difficulty in playing this kind of role -- a huckster who might actually believe what he's selling, and a historical figure who has become deified by some and demonized by most -- but Hoffman treats the material with his typical buoyancy. He's allowed to be huge, to a nearly galactic degree, while retaining an element of realism that permits him to be utterly knowable. Dodd isn't just a visionary behind an ever-expanding cult, he's the small-town used-car salesman or the part-time hood who is always dreaming of something bigger. The sequences with Phoenix are astonishing feats in and of themselves, and one pivotal moment with his wife (played by Amy Adams) brings into question just who, exactly, the Master is. If there's one movie that displays the kind of power, charisma, and mystifying complexity of Hoffman's craft, then it's "The Master," a movie so far ahead of its time we're still catching up to it, even now.