The Best Films of Philip Seymour Hoffman

Mary and Max is the tale of an overlooked 8-year-old girl from Australia starting an unlikely friendship via mail with a middle-aged Jewish man from New York. Shot completely in monocromatic claymotion, it is the first feature film by Australian stop-motion animation writer, Adam Elliot, and the first ever animated film to score the opening slot at Sundance Festival. In all its playful absurdity, Mary and Max is an emotional and wise gem of a film that examines the human condition through the eyes of a troubled child and an autistic American. In contrast to its clay-based animation, it deals with some pretty dark and adult themes, but succeeds in balancing those with happiness and absurd humor. Moreover, Elliott gathered an ensemble cast to do the voice-overs, which includes Philip Seymour Hoffman, Toni Collette, and Eric Bana. We recommend it 8 condensed milks out of 10.

Adam Sandler, though currently imminently marketable, incredibly played out and boring, used to be a real actor. This is the film by which his legacy will be judged, where we see the funnyman drop the mask and actually show real feelings besides bumbling rage. Sandler’s hurt and confused performance is beautifully vulnerable and true and is complimented by P.T. Anderson’s incomparable direction (the man behind Boogie Nights and There Will Be Blood), creating a true masterpiece of American cinema. This beauty also stars Philip Seymour Hoffman and Emily Watson.

A slow-burning US political drama, The Ides of March is a character-driven film with great performances from Ryan Gosling, Philip Seymour Hoffman and George Clooney (who is also the director and in part the writer) among many others. Taking place during the last days of the primaries, Stephen Meyers (Gosling) is an aspiring campaign staffer who uncovers a dirty truth about his candidate (Clooney). When Meyers confronts his boss (Hoffman), moral issues arise that collide with the political profession but which are not only limited to it. A smart film, The Ides of March is less of a political thriller and more of a really well made drama that delivers.

Based on the book by John Le Carre, this slow-burning thriller tells the story of a half-Chechen, half-Russian immigrant suspected of terrorism, who is suddenly spotted in a big German city trying to get his hands on money that was left to him. Gunter (played by Philip Seymour Hoffman) is the head of an international counter-terrorism unit created after 9/11 to spot threats like these early on. Whether this man is a terrorist or not, what he is doing in Germany, how he fits in the grand scheme of things, and whether Gunter will succeed in his efforts – all of these are questions you will be begging to find answers for. Witty, supremely acted, and with a very provocative story line, A Most Wanted Man is perfect if you’re in the mood for a sharp thriller.

The 2008 film Doubt offers a haunting peek into the crisis of pedophilia within the Catholic church. Featuring an all-star cast of Amy Adams,  Philip Seymour Hoffman, Meryl Streep and Viola Davis, it is more than just a fictional tale. With performances that will make you question your intuition and cast a shadow of doubt on your own instincts, Doubt is a difficult film to grapple with. 

I fell in love with this film very early on into the duration of it because it was so honest and it allowed the characters to navigate the nature of their suspicions. With Doubt, however, comes denial, and Viola Davis’s eight-minute monologue is simply smeared with it. Doubt is a fantastic story that has left me stunned for over a decade. 

Already featuring some of the desperation and melancholy that would go on to characterize most of his work, Paul Thomas Anderson’s Hard Eight manages to draw palpable suspense and drama out of, essentially, three characters and a couple of seedy locations. We learn perhaps too little about these characters and why this veteran gambler is drawn to a young homeless man, but there’s also something intriguing about how Anderson suggests much larger and much crueler stories going on just out of sight. It truly feels like these people are just trying to hold on to the smallest things that ease their pain—which works because of incredibly compelling work from Philip Baker Hall, John C. Reilly, and a young Gwyneth Paltrow already at the top of her game.

Philipp Seymour Hoffman stars in this family drama next to Laura Linney as siblings. They have to unite to support their father who after the death of his girlfriend finds himself alone. The Savages, after the family name, have dynamics that are all too common and easily recognizable. This is a beautiful and real movie.

One of those long-lost mid-budget dramas that’s content with observing the rich yet uneventful lives of average folk, Nobody’s Fool reminds us that nothing exciting or shocking needs to happen to make a good story. The late, eternally charismatic Paul Newman leads an ensemble of character actors in relaxed, memorable roles—Bruce Willis, Philip Seymour Hoffman, Margo Martindale, and Jessica Tandy, among others. It’s the authentic, neither-love-nor-hate relationship among all these characters that drives all their individual drama forward and keeps the film from stagnating into anything less than endearing. Here, the idea of things never really changing in this small community is meant to be a comfort, not a lament.

Set in the 1930’s English Countryside, the story of the eccentric Mortmain family is told from the daughter Cassandra’s point of view. Her father, a once acclaimed and famous writer has written nothing in years, leading the family into bankruptcy. Themes such as first love and financial troubles are explored from Cassandra’s comic and intelligent point of view. A classic and a must-see.

Happiness is a difficult, disturbing watch. Unlike films that claim to be brave, Happiness actually goes there and shows us just how deep, dark, and perverse our urges can get. But far from being controversial for the sake of it, this fearless film has important things to say about the facade of happiness, the urgency of loneliness, and the futility of feigning ignorance about both. And it does so with an impressively wry humor delivered by a talented cast that includes Philip Seymour Hoffman, Lara Flynn Boyle, and Dylan Baker. They play their complicated characters so well, they’ll have you thinking about the strange ways you can, in fact, relate to them on some level, long after the credits roll. 

This isn’t a film you’ll want to revisit often, but you will have to see it at least once in a lifetime—if anything, for the kind of painful honesty you’ll rarely find anywhere else.