Philip Seymour Hoffman is an easy actor to love—praised by critics, adored by fans and winner of the Academy Award for Best Actor. Starting his career barely 20 years ago, his countless memorable performances include Almost Famous, Capote and Boogie Nights. In honor of The Master, his upcoming film with Paul Thomas Anderson (their fifth project together), we dug into his IMDb page to decide what our favorite PSH performances were—and man, was it hard keeping it to 10.
10. Lester Bangs, Almost Famous (2000)
Although legendary rock journalist Lester Bangs appears only in brief scenes throughout the movie, his part is a pivotal one thanks to his superb performance. Hoffman embodies the drug-addled, off-the-cuff humor and rock-star disenchantment that has come to define the iconic writer, providing a stand-out performance in just a handful of scenes.
9. Lenny Savage, The Savages (2007)
Hoffman balances Laura Linney’s neuroticism pitch perfectly in The Savages, a film about a brother and sister who are forced to take care of their once-abusive father as he slowly dies. He doesn’t become a hero under the circumstances, but neither does he buckle, remaining stoic while walking a fine line in a performance everyone can find a bit of themselves in.
8. Brant, The Big Lebowski (1998)
The Big Lebowski is filled with large, loud-talking slackers, but Hoffman again stands out in his small role as Brant, the other Jeffrey Lebowski’s lap dog. Becoming a sniveling sycophant is no easy task for an actor who often plays dispassionate characters, but Hoffman manages to accomplish it almost instantly: “You didn’t go to college…”
7. Gust Avrakotos, Charlie Wilson’s War (2007)
Hoffman’s portrait of the crazed, foul-mouthed CIA agent in the political biopic earned him a well-deserved Oscar nod. He balances the film against Tom Hanks’ performance as Congressman Charlie Wilson, managing to outshine him.
6. Jacob Elinsky, 25th Hour
In the Spike Lee-directed film about Monty Brogan (played by also fantastic Edward Norton) and his last 24 hours before going into jail, Hoffman’s character stands by his childhood friend throughout the night. A high-school teacher with the hots for one of his underage students, the role could have easily turned polarizing, but as with so much of Hoffman’s work, he brings out all the character’s intricacies to make him sympathetic rather than merely reprehensible.
5. Caden Cotard, Synecdoche, New York (2008)
In a film about dreams and decisions and death, the viewer watches Hoffman age from his 30s through the end of his life. And while the manner in which he visually ages is miraculous, watching his character mentally evolve in tandem is equally engaging, as he tries to wade through the never-ending list of failures stacked against him.
4. Andy Hanson, Before the Devil Knows You’re Dead
It is hard to be likable when playing a man who plans to rob his own parents, inadvertently kills his mother and murders a half dozen people in cold blood to try and cover his tracks. And while Hoffaman’s take on Andy Hanson could scarcely be called likable, it is eerily relatable: You may not kill one of your parents to fund your laundering and drug habit, but his desperation to escape from a situation he has both created for himself and is trapped in is oddly resonant.
3. Scotty J., Boogie Nights (1997)
Scotty J. was Hoffman’s breakout role, and remains one of his most memorable. As an overly excited soundman with the supreme hots for Mark Wahlburg he created a name for himself, among a fantastic cast that he could have easily simply been lost in.
2. Father Flynn, Doubt (2008)
The entirety of the film Doubt circles around the nagging emotion it’s named for, leaving the viewer with no true take on Hoffman’s character. In his role as Father Flynn, the father at a church in the Bronx who may or may not be having an illicit relationship with an alter boy, Hoffman’s performance walks the line perfectly, alternately convincing the viewer both that he’s guilty and being wronged.
1. Truman Capote, Capote (2005)
Managing a drastic change of voice and somehow seeming to act almost a half a foot shorter, Philip Seymour Hoffman becomes the effiminate and over-the-top personality that was Truman Capote. Even with second Capote biopic Infamous coming out the same year, Hoffman completely shined in what we consider to be his best and most challenging role, the one which earned him an Academy Award for Best Actor.