Philip Seymour Hoffman: 5 smaller roles that helped make him great

Philip Seymour Hoffman in 1992 as George Willis Jr. in 'Scent of a Woman' (Universal/Everett Collection)

One day after the news of Philip Seymour Hoffman’s death, there’s plenty of discussion online about the number of quality roles he’s played since he broke into films in the early ‘90s.

Like with any great character actor, there are movies he’s been in which you could point out and you might get the response: “Wait, he was in that? … You’re RIGHT.”

Seymour Hoffman was well known for his ability to dig deep into the shame and hurt that underlies many of the characters he’s played (in “Boogie Nights” and “Happiness,” to name a few). But he’s also a master of playing larger than life, brash and utterly unlikable. Or so unlikable he somehow becomes lovable.

It’s in small roles earlier in his film career in which he’s appeared and made a big impact in the eyes of many – including notable directors and producers who took notice. Here are 5 that stand out for us:

Film: Scent of a Woman

Role: George Willis Jr.

Year: 1992

Al Pacino’s scene-chewing histrionics aside, when you’re looking for a model of the obnoxious and privileged, Seymour Hoffman’s portrayal of prep school student George Willis Jr. comes immediately to mind. This is the performance that caught director Paul Thomas Anderson’s attention, and five years later he gave the role of Scotty J. in “Boogie Nights” to Seymour Hoffman.

Film: Nobody’s Fool

Role: Officer Raymer

Year: 1994

The young Seymour Hoffman clearly wasn’t intimidated acting alongside legends Paul Newman and Jessica Tandy, not to mention Bruce Willis and Melanie Griffith. His small-town bumpkin of a police officer in the New York village of North Bath is a delight to watch.

Film: Hard Eight

Role: Young Craps Player

Year: 1996

Seymour Hoffman spends no more than 3 minutes on screen in this early Paul Thomas Anderson film, but he nearly steals the film, playing a mullet-haired gambler with no respect for his elders (specifically, an old-time gambler played exquisitely by Philip Baker Hall). He brings a full commitment to his roles, big or small, and is nuanced and unforgettable here.

Film: The Talented Mr. Ripley

Role: Freddie Miles

Year: 1999

Playing a Princeton friend of Dickie Greenleaf (Jude Law), Seymour Hoffman’s Freddie Miles is the epitome of smarm (without somehow being loathsome -- this could be George Willis Jr. in 5 years). How he plays his suspicion and contempt towards Matt Damon’s character Tom Ripley is remarkable.

Film: Punch-Drunk Love

Role: Dean Trumbell

Year: 2002

Seymour Hoffman is a mattress-selling conman that torments Adam Sandler’s Barry Egan. He’s pretty much cornered the market on contemptible characters who are delightful to watch. How does he do it? He gives them generous doses of humanity with an underlayer of deep insecurity.