The Best Movie Ever: Philip Seymour Hoffman

Best Philip Seymour Hoffman Movie Ever

The world still mourns the untimely passing of Philip Seymour Hoffman, one of the great actors of his generation, who died earlier this year on February 2, 2014. The Oscar-winning star of Capote left behind dozens of incredible performances and, being the hard-working thespian that he was, several more that are still coming to theaters.

With his second-to-last film arriving this weekend – The Hunger Games: Mockingjay, Part 1 – we wanted to take another opportunity to celebrate the career of Philip Seymour Hoffman with a very special installment of The Best Movie Ever. This week, as always, we have challenged our film critics William Bibbiani, Witney Seibold and Brian Formo to look at a single category of film and pick one single movie that represents the absolute best of it.


Related: Philip Seymour Hoffman: 10 Unforgettable Performances


Needless to say, they have their work cut out for them this week. Picking just one Philip Seymour Hoffman performance is like picking just one Beatles song. In the end, it may just boil down to personal preference. So we leave the final decision to you. What’s YOUR favorite Philip Seymour Hoffman movie? You can let us know by voting at the bottom of the page.


Check Out: The Best Movie Ever: Dumb Comedies


Witney Seibold’s Pick: Happiness (1998)

Happiness Philip Seymour Hoffman 

When Philip Seymour Hoffman unexpectedly died back in February, there was an outpouring of affection for the beloved thespian. Although the appellation is thrown about recklessly, it actually applies here: Hoffman was an actor’s actor. He was no mere celebrity or movie star. He was a steely and dedicated performer, a man who used his threatening talent to dredge up the most disgusting and unappealing parts of his characters. Even when playing a broader and more melodramatic caricature – as he did in Mission: Impossible III – he went for humanization rather than scenery chewing. He was never afraid to play undesirable or oblique, and yet still took up the screen, and your attention, with his own curious breed of anti-charm. Not that he couldn’t also be amusing and charming; watch Twister at some point. 

When choosing the best Hoffman film, I find myself sort of at a loss. Do I select his noisy supporting turn in Punch-Drunk Love? His sad sack porno boom operator from Boogie Nights? His Oscar-winning role as Truman Capote? His completely underrated turn in the amazing Before the Devil Knows Your Dead? His quiet one-track momentum in Owning Mahowny? The uncool voice of wisdom in Almost Famous? There are too many to select from. The encapsulation of the entire human experience in Synecdoche, New York

I think I’m going to have to select the Hoffman role that first caught my attention. In 1998, Hoffman appeared in one of the most harrowing suburban dissections in an era that was lousy with them. Todd Solondz’ Happiness is a heart-wrenching tale of several people whose subtle illegal appetites are ripping up the guts of the American suburban idyll from the inside. There is a pedophile, a rapist, a string of clueless spouses, and, most notably, an obscene phone caller played by Hoffman. Hoffman’s character, Allen, wears uncomfortable-looking suits, sweats, sputters, and has no social grace. He grunts on the telephone, and seemingly can only communicate through desperate obscenity. And while Solondz doesn’t make up sympathize with him, Hoffman turns him from a cartoonish criminal into something disturbingly real and relatable. Sometimes, our own appetites get the better of us. Here’s what we look like when that happens. 


Brian Formo’s Pick: The Talented Mr. Ripley (1999)

The Talented Mr Ripley Philip Seymour Hoffman

Philip Seymour Hoffman was an exemplary performer. And while he emerged from supporting cast staple to leading man for Capote, Love Liza, Synedoche, New York, The Master and most recently, A Most Wanted Man, more than any other actor of the past decade I’ve relished his smaller roles that made you hope his character would appear again. Though I wouldn’t call this the best film that Hoffman has starred in, or even his best performance (I do believe that’s The Master), but despite how great Matt Damon was in The Talented Mr. Ripley, I just wanted to see more Freddie Miles (Hoffman). To me that’s the biggest crater of Hoffman’s shortened career: those smaller performances that felt as though Hoffman could have an entire film developed for a character who only drifts in intermittently.

When Hoffman repeated the “I’m a fucking idiot” line in Boogie Nights, he became a character actor star. The reason why that line, repeated eight times, doesn’t become campy is because each time Scotty says it again, it feels more real. Repetition: that’s how we beat up ourselves. 

In The Talented Mr. Ripley, Hoffman uses repetition to debase someone other than himself; smug, and awfully. “How’s the peeping, Tommy?” is a simple line made menacing by Hoffman because he says it with personal amusement, and then repeats the more-familiar-than-they-are name “Tommy” over and over when he doesn’t get an answer. It’s verbal whack-a-mole on another, perceived lesser, human being. 

Tom (Damon) and Freddie are on a boat, invited by young and rich playthings Dickie (Jude Law) and Marge (Gwyneth Paltrow). Freddie is aware that Tommy doesn’t belong in their pre-determined company: there’s a class and private education barrier. But instead of outright admonishing him in a villainous manner, Freddie waits for a moment that’s personally embarrassing and private between just the two of them. He catches Tom looking at Dickie and Marge removing each other’s swimming bottoms below deck. The smugness of Freddie in that scene is deplorable, but Tom isn’t defensible, either. “How’s the peeping, Tommy?” Before Freddie shows up, we feel why Tom is drawn to Dickie. But with Freddie by his side, dancing with a friendly familiarity, Dickie begins to lose some of his luster and appeal. That Hoffman did so much with a role that came fifth in the credits – and that he did that with regularity! –  was his greatest achievement as an actor.


William Bibbiani’s Pick: Punch-Drunk Love (2002)

Punch-Drunk Love Philip Seymour Hoffman


That line of dialogue is mostly just screaming. It is a testament to the late Philip Seymour Hoffman’s unassailable acting prowess that it’s also deeply meaningful and hilarious. In Paul Thomas Anderson’s lauded-yet-still-underrated Punch-Drunk Love, Hoffman plays Dean Trumbell, one of the most believable yet unlikely villains of the 21st Century. He has power because he believes he has power, and not because his twin occupation as the owner of a mattress store and proprietor of a phone sex line actually gives him any. 

To Barry Egan (Adam Sandler, in his best performance), a character with no self-confidence, a figure like Dean Trumbell is an almighty adversary. Barry never learns that Dean’s goons have limited resources, and have to save their receipts. He never learns that Dean’s criminal empire consists entirely of the back of not particularly successful store. Barry only knows that the voice on the other end of the phone is more confident than his own, and in the end he only gets his life back from Dean’s simplistic attempts to extort money by sounding even stronger.

For a bad guy who comes to represent something larger than himself, Dean Trumbell is surprisingly small. But that’s the point, really. His circumstances aren’t much different than the hero’s: he owns a tiny business, he has a side project that skirts the rules, he’s surrounded by a supporting cast of frustrating eccentrics. But unlike Barry, he dominates his own circumstances. As played by Philip Seymour Hoffman as a slightly scary a-hole, Dean Trumbell emerges as one of the most distinctly significant antagonists around. As little as anyone, but as great as he wants to be.


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