The 15 Best Roles of Philip Seymour Hoffman

Bryan Enk
Yahoo MoviesFebruary 2, 2014

Philip Seymour Hoffman was found dead today at the way-too-young age of 46, leaving behind a legacy of terrific screen roles filled with memorable scene-stealers, intense antagonists and wily anti-heroes.

There really isn't another actor out there quite like Philip Seymour Hoffman. Really, if you had PSH in mind for a role, only PSH would do — and he came from theatre, so you know he had real cred when it came to this whole 'acting' thing. He was one of Paul Thomas Anderson's go-to muses, a reliable character actor and an underrated leading man ("Capote," anyone?) who was probably just getting started in showing us what he had in him.

Here are our 15 favorite roles of Philip Seymour Hoffman, with Honorable Mentions going to his Oscar-nominated performance as Father Brendan Flynn in "Doubt" (2008) as well as his portrayals of Rusty Zimmerman in "Flawless" (1999), Joseph Turner White in "State and Main" (2000), Caden Cotard in "Synecdoche, New York" (2008), Paul Zara in "The Ides of March" (2011) and many others.

[Related: Philip Seymour Hoffman Dead at 46]

1. Truman Capote, "Capote" (2005)

PSH scored an Oscar for his nuanced performance as author Truman Capote, whose uneasy relationship with convicted murderer Perry Smith (Clifton Collins Jr.) inspires the writing of his famous book, "In Cold Blood." PSH later reunited with director Bennett Miller for another true-life drama, "Moneyball" (2011).

2. Lancaster Dodd, "The Master" (2012)

PSH's fifth — and final — collaboration with Paul Thomas Anderson featured one of his most flamboyant and powerful performances. As cult leader Lancaster Dodd, PSH gathered an army of worshipers, mostly made up of lost souls like Freddie Quell (Joaquin Phoenix), wandering post-WWII America in search of meaning ... and leadership. "Leave your worries for a while, they will still be there you get back, and your memories aren't invited."

3. Scotty J., "Boogie Nights" (1997)

One of the most heartbreaking characters in Paul Thomas Anderson's bittersweet love letter to '70s- and '80s-era porn is PSH's Scotty J., a splinter member of porn mogul Jack Horner's (Burt Reynolds) ensemble of California misfits/adult film stars. His self-loathing, tearful breakdown in his car after he attempts to kiss his crush Dirk Diggler (Mark Wahlberg) is especially moving.

4. Gust Avrakotos, "Charlie Wilson's War" (2007)

PSH got to play alongside such Hollywood heavyweights as Tom Hanks and Julia Roberts in director Mike Nichols' account of U.S. Congressman Charlie Wilson (Hanks) joining forces with CIA operative Gust Avrakotos (Hoffman) to launch Operation Cyclone, a program to organize and support the Afghan mujahideen during the Soviet war in Afghanistan. For the record, neither Hanks nor Roberts received Oscar noms for their performances ... unlike PSH.

5. Art Howe, "Moneyball" (2011)

PSH's second team-up with director Bennett Miller following their successful "Capote" (2005) endeavor sees him in the role of Art Howe, the Oakland Athletics manager who isn't a fan of the radical new method in scouting and analyzing players conjured by his colleagues Billy Beane (Brad Pitt) and Peter Brand (Jonah Hill). PSH brings a kind of scowling, exhausted antagonism to this recreation of behind-the-scenes baseball politics ... sometimes comically so as he's rarely seen not in his A's player uniform.

6. Phil Parma, "Magnolia" (1999)

One of the all-time greatest 'guardian angel' characters in the history of cinema is definitely Phil Parma, the male nurse of cancer-stricken Earl Patridge (Jason Robards), in Paul Thomas Anderson's amazing ensemble character drama/semi-fantasy. From his very first beat — tenderly touching Patridge in greeting and asking with a smile, "How's today?" — PSH hits the role out of the park.

[Related: Photos - The Many Faces of Philip Seymour Hoffman]

7. Plutarch Heavensbee, "The Hunger Games: Catching Fire" (2013)

One of PSH's most recent gigs had him catching "Hunger Games" fever in the role of Plutarch Heavensbee, an associate and confidante of the corrupt and ever-scheming President Snow (Donald Sutherland) who might not be all that he appears to be. Lionsgate has reported that Hoffman had already shot nearly all of his scenes the series' two-part finale, "Mockingjay."

8. Freddie Miles, "The Talented Mr. Ripley" (1999)

"Tommy. Tommy, Tommy, Tommy, Tommy, Tommy ..." PSH stole scenes from the likes of Matt Damon, Jude Law, Gwyneth Paltrow and Cate Blanchett in the role of Freddie Miles, a charming yet somewhat creepy spoiled rich kid who eventually became keen to the psycho shenanigans of Mr. Ripley (Damon). Such knowledge made him one of Ripley's victims, but not before he upstaged his co-star at every turn.

9. Jacob Elinsky, "25th Hour" (2002)

PSH brought repressed melancholy to the role of English teacher Jacob Elinsky in Spike Lee's terrific post-9/11 NYC morality play, serving as the voice of reason and restraint as convicted drug dealer Monty Brogan (Edward Norton) has one last wild night of freedom with his pals. Then again, restraint only goes so far when one of your students looks like Anna Paquin.

[Related: Hollywood Mourns Philip Seymour Hoffman on Twitter]

10. Lester Bangs, "Almost Famous" (2000)

PSH apparently had the flu when he filmed his handful of scenes for Cameron Crowe's nice-guy tribute to sex, drugs and rock n' roll, bringing a kind of cagey coolness to the role of veteran Rolling Stone journalist Lester Bangs, who shares his music journo wisdom with young protege William Miller (Patrick Fugit).

11. Andy Hanson, "Before the Devil Knows You're Dead" (2007)

Director Sidney Lumet's final feature film before his death in 2011 was this intense family/crime drama in which two brothers scheme to rob their parents' jewelry store. Things go awry to the point where it becomes hard to watch, with PSH bringing the rage as older brother Andy, whose wife (Marisa Tomei) is having an affair with his younger sibling (Ethan Hawke).

12. Dean Trumbell, "Punch-Drunk Love" (2002)

"No, SHUT UP. Shut, shut, shut, shut, SHUT UP!!" PSH brought bullying villainy to the role of Dean Trumbell, the 'mattress man' whose phone sex operation tries to scam poor Barry Egan (Adam Sandler) in Paul Thomas Anderson's terrific weirdo comedy. PSH also played the character in the rather hilarious "Mattress Man Commercial," featured on the "Punch-Drunk Love" DVD.

13. Jon Savage, "The Savages" (2007)

One of PSH's best-ever 'leading man' gigs had him teaming up with Laura Linney to play two estranged siblings who reunite to care for their father (Philip Bosco), who is slipping into dementia. "The Savages" is so far one of the best 'dysfunctional family' dramas of the 21st century, a much-recommended alternative to the exhausting emotional bombast and histrionics of the recent "August: Osage County."

14. Owen Davian, "Mission: Impossible III" (2006)

PSH reunited with his "Magnolia" pal Tom Cruise for the third installment of the "Mission: Impossible" series, in which he got to go all summer-movie super-villain on us as arms dealer Owen Davian, the latest threat to national security that must be stopped by Ethan Hunt (Cruise) and his gang of impossible mission-goers.

15. Sandy Lyle, "Along Came Polly" (2004)

PSH got to show off his mad comedy skills in the role of Sandy Lyle, "the kid from 'Crocodile Tears,'" in this otherwise mediocre bit of Ben Stiller/Jennifer Aniston silliness. This one gets notice if only for PSH's perfect delivery of "I just sharted" — and his various exclamations as he attempts to put a basketball through a hoop ("White chocolate!" "Iceman!" "Raindrop!") are pretty good, too.