Try this out as an exercise in futility: Name Philip Seymour Hoffman’s greatest film role.

A close friend and I tried in the hours following the tragic news that we’d no longer get future Hoffman performances to consider. Twitter flooded with admiration for Hoffman’s work in the prestigious (Capote, Doubt, The Master), the accessible (The Hunger Games, Mission: Impossible III) and the iconic (The Big Lebowski, Almost Famous). Scan his resume. Your jaw literally drops at the sheer number of outstanding roles Hoffman delivered in his scant 46 years on this planet. He was one of our greatest living actors.

We here at CinemaBlend are devastated that this incredible talent was cut short, with so much left to give. But we’re choosing to counter our sadness with a celebration, of sorts. We combed through his filmography and selected our five favorite PSH roles. In doing so, we easily left 25 amazing performances in the lurch. Such is the incredible output of Hoffman’s. But these are the performances we’ll always hold dear, with an attempt to explain to you why.

Which roles would you choose?

Magnolia
As hospice care nurse Phil Parma in Magnolia, Philip Seymour Hoffman approached the role with exactly the kind of patience, determination, kindness and incredible compassion one might expect from a person tasked with caring for a terminally ill patient. In a film that ties a lot of characters together, Hoffman's character never really gets his own story, but we learn plenty about the kind of man Phil is through his actions, and Hoffman's talent certainly isn't wasted in the role.

Parma's involvement among the ensemble in Paul Thomas Anderson's film serves as a crucial connector between Jason Robard's Earl Partridge and his estranged son, Frank Mackey (Tom Cruise). As a caretaker for Earl, Parma goes above and beyond to try to track down Earl's son, whether it means taking on an extra shift, patiently relaying Earl's situation to people who might be able to help him find Frank, calmly responding to the emotional reactions of Earl's wife (Julianne Moore) and at one point, awkwardly ordering pornographic magazines through a grocery delivery service in the hopes of finding one of Frank's self-help seminar ads. Parma patiently does what needs to be done to make this reunion happen before Earl dies, and in the process of portraying this man, Hoffman demonstrates his ability to play a genuinely kind and selfless human being, who proves to be a stark contrast to some of the other roles Hoffman has played, including the sleazy Dean Trumbell in Punch-Drunk Love, the music-loving know-it-all Lester Bangs in Almost Famous or the contemptuous Freddie Miles in The Talented Mr. Ripley, to name a few examples.

Hoffman was an actor with range. He could be funny, awkward, dramatic, dark and anything else a role called for. His body of work is a demonstration of his talent and his performance in Magnolia is no exception there.

Synecdoche, New York
There’s no easy guide on playing someone like Caden Cotard, the protagonist of Charlie Kaufman’s Synecdoche, New York. As befitting writer/director Charlie Kaufman, Cotard is not your typical lead character, -- a disgruntled New York playwright who places his life on hold to pursue a work that he finally deems true and real. He’s a character who has to appear intelligent in an attractive manner, but also distant… an inscrutable mess who can’t seem to keep track of his marriages or the age of his daughter. He has to be both maddeningly specific, but also a man lost in a slipstream of regret, emotional abuse and loneliness as he ages before he can count his own accomplishments.

It’s difficult to imagine anyone but Hoffman making this character affectingly concrete, both tragic and inherently unlikable. It’s a performance without vanity: Cotard’s body crumbles and his humiliations reach outlandishly scatological lows. But Hoffman has always had a deep reservoir of sadness and rejection, even in his most blustery roles. Kaufman’s film rarely takes you outside Cotard’s world, and so it’s Hoffman’s task to illustrate the feeling that Cotard’s unfinished experiment (a play within a play within a play within…) is wearing on him as well as his loved ones. He shatters so convincingly in this picture, to the point where it’s probably the most difficult film to watch in the wake of Hoffman’s sudden passing. When he finds the remnants of a gift he procured for his daughter in an abandoned alley, it’s as if a million mirrors have been shattered simultaneously, even as Kaufman downplays Hoffman’s typically-volcanic emotional explosion.

Difficult and dissonant, Kaufman and Hoffman’s collaboration is typical Hoffman: abrasive, difficult, funny and ultimately, deeply, life-affirming.

The Big Lebowski
Starring in a Coen brothers film almost necessarily means an actor will deliver one of the most memorable performances of his or her career, and Philip Seymour Hoffman put his best and most auspicious foot forward in The Big Lebowski for the role of Brandt. A "Yes Man" to the nth degree, Brandt stands tall in a century of cinematic butlers with a nose browner than the Kahlua in the Dude’s White Russian. Good help is hard to find, but Brandt will almost certainly help you look for it.

As the servant to the disabled Lebowski namesake, Brandt is the always-smiling, verbal biographer of his employer, but he’s also one of the only characters who is sympathetic towards the bearded toker at the film’s center. While most uppity people would just make The Dude sit and wait in the least expensive chair in the house, Brandt is warm and welcoming, quick to point out the many accolades that Lebowski has earned, as if that will somehow excuse his rude demeanor. He is visibly intimidated by his boss, and I like to think after the credits have rolled that Brandt rented an apartment near the beach and turned his stiff-lipped introversion into sandal-wearing extroversion, free from pinky toes and mansions with candles in every room. Maybe he could work on his laugh, as well.

The Big Lebowski came at a key point in Hoffman’s career, right alongside his depressed neighbor in Todd Solondz’s Happiness, and between his memorable supporting turn in Paul Thomas Anderson’s Boogie Nights and as the doting nurse in Anderson’s Magnolia. Brandt was arguably Hoffman’s most cult role, and always the one that I think of first when his name is brought up. To quote the character himself, "Perhaps we’ll see you again sometime, Dude."

Almost Famous
Every journalist needs a Lester Bangs – a veteran who has been in the "trenches" and can pass along vital secrets about how to survive. Hell, that mentor role is vital to virtually any profession, but they are extremely important when an up-and-comer like William Miller (Patrick Fugit) is attempting to enter and maneuver an alien environment like "rock-and-roll." Lester is William’s foot in the door. He hands him his first assignment, inviting him behind the velvet rope where a music-loving nerd could only dream of landing. He’s the person William can point to when proving that there’s a career in this, and the person he can lean on when that career choice starts to sound like suicide.

Hoffman, as he has numerous times, has to walk a very complicated line in Cameron Crowe’s Almost Famous, and to the surprise of no one, he nails it. To William – and to the audience – he first must appear as the epitome of cool. William waits outside of a radio station just to meet Lester, and when it becomes clear no one else has, the rock-journo icon is able top drop his guard. But it’s Hoffman’s explanation of the power of the "uncool" that gives Famous its spine… and the whole movie rests on that truth as young William gets seduced by music, by Penny Lane, by Stillwater – by rock and roll. Though he was only in his mid-30s at the time, Hoffman sold a character who had lived a lifetime, and was anxious to share his experience with the next generation so that they could learn from his mistakes (and maybe make a few of the same ones, as well). It’s one of Hoffman’s warmest, kindest and most honest performances, and it goes a long way to explaining why Famous stands out as one of Crowe’s finest, ever.

Punch-Drunk Love
Philip Seymour Hoffman was so talented that he could morph to play any character that a story needs, but one side we could never get enough of is when he would star as one of the bad guys. The actor was able to summon an incredible, intense energy that would fuel his antagonist roles, and when heroes were going up against him, you knew that there was a hard-fought battle ready to be had. No place in Hoffman’s career does this energy come out better than in his turn as the nefarious Dean Trumbell in Paul Thomas Anderson’s Punch Drunk Love.

It may not be the flashiest or even the most famous part of his career, but Hoffman’s turn in the bizarre romantic comedy is nothing if not memorable. Playing a man who owns both a phone-sex line as well as a mattress store, the Academy Award-winning actor spends most of his role in the movie pulling strings behind the scenes, doing his part to make the lead, Barry (Adam Sandler), miserable. But the performance all comes boiling down to a singular in-person confrontation that has the film’s protagonist and antagonist together in the best way possible.

From his over-the-top shouting match on the phone ("Did you just say go fuck myself?" "Yes, I did." "That wasn’t good!") to his final line in the movie, said in the most chicken-shit way possible ("That’s that!"), the character is one of Hoffman’s most oddball creations, and it’s amazing to watch every brief second of it. There were few actors who could take as limited a role as Dean Trumbell in Punch Drunk Love and turn it into something truly brilliant, but it really just speaks to Hoffman’s brilliant talent as an actor.

Boogie Nights
A strong case could be made that there are 10 characters with more textual depth and more of a presence in the Boogie Nights screenplay than Scotty J, the gay boom mic operator with a massive crush on Dirk Diggler. Amidst all the bigger personalities and more shocking downfalls, he’s just not that important to the greater story arc, but in the skilled hands of Philip Seymour Hoffman in one of his first major Hollywood roles, Scotty winds up being so much more. In a weird way, he turns into one of the most genuine, caring and complicated characters in the entire film, a piece so vital it’s impossible to even picture the larger story without him.

Anytime an actor is playing a man who’s awkward, a man who could be considered a bit of a joke, there’s a clear choice he needs to make. He can either turn the dial up on all the negativity and all the unintentional buffoonery or he can dig deep within that graceless, floundering exterior and find something beautiful and human within him. In other words, he can be a funny caricature or he can be a familiar weirdo. Hoffman picked the latter. That might sound obvious, like it’s a conscious choice an overwhelming majority of actors would make, but the truth is it takes balls to turn the knob down and stay away from the easy jokes. It takes extreme confidence to avoid overacting and trust tones of voice and careful dialogue to win out in the long run.

Boogie Nights was the first indication for most of us of just how brilliant Hoffman could be, and as long as movie fans are sitting through that brilliant film, they’ll continue to walk away, thinking and smiling about Scotty J.

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