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Boogie Nights, 1997
The first of several successful collaborations with Paul Thomas Anderson, Hoffman played Scotty J, the gay boom operator who falls for Mark Wahlberg's well-endowed Dirk Diggler. Some consider this to be his breakout role.
The Big Lebowski, 1998
Who can forget Hoffman's role as the officious butler in this Coen Brothers classic?
This Paul Thomas Anderson ensemble masterpiece is filled with incredible performances. Hoffman plays Phil Parma, a nurse caring for a dying man who wants to be reunited with his estranged son — and he brought great humor and pathos to the role.
The Talented Mr. Ripley, 1999
It was Jude Law who snagged an Oscar nod for this period thriller starring Matt Damon and Gwyneth Paltrow, but there's no denying Hoffman's effortless turn as the ultimate snob, Princeton grad Freddie Miles.
Almost Famous, 2000
The only problem with this Cameron Crowe classic is there are not enough scenes with Hoffman playing legendary music critic Lester Bangs. The character is unmerciful and uncool, yet somehow manages to inspire generations of wannabe rock writers who will (hopefully) never look at Jim Morrison in the same way.