Two of my favorite actors of their generation are/were Philip Seymour Hoffman and Paul Giammati.
Neither of them had leading man good looks (Many would say far from it for Philip Seymour Hoffman) but both were able to provide great performances in many varied roles.
PSH had so many great performances, that it was tough to narrow it down. I have ranked my favorites but I realize that you re-order this list in so many ways.
1. Owning Mahowny-
I'm guessing that most have not seen this role. I have seen it several times and PSH makes me think I am watching a documentary of Dan Mahowny rather than a film adaptation!!
Here's a clip:
2. Almost Famous- Lester Bangs
3. Scent of a Woman- one of his very first roles. When you watch it now, it's hard to believe that is Hoffman.
4. Along Came Polly- Sandy Lyle
- except for Jennifer Aniston, the only good thing in this movie. In a minor role, steals the film.
5. Big Lebowski
- You wanted to punch him in the face in the Big Lebowski. Admit it.
6. Before the Devil Knows You're Dead
- Gets to have sex with Marisa Tomei in this flick. Highly recommend it.
- Not a huge fan of this flick but PSH won an Oscar and he nails the role!!
8. The Invention of Lying
- Another minor role, playing Jim the Bartender. Usually on screen with Louis CK and Ricky Gervais, I laugh at almost everything he says.
9. Love Liza
-plays a man trying to deal with the suicide of his wife. Strong performance.
10. (Tie) Pirate Radio- again, not a great movie except for Hoffman
Nobody's Fool- a very minor role as Officer Raymer
Honorable Mention: Magnolia (did not like this film at all, but PSH is very good in his supportign role); Jack Goes Boating; The Savages: Punch Love Drunk; and, State and Main
I still need to see: Boogie Nights; Charlie Wilson's War; The Talented Mr. Ripley; Doubt; The Master; Ides of March; Moneyball; Happiness; Flawless; and, A Late Quartet.