Scent of a Woman (1992) — George Willis Jr
Hoffman had to audition five times for the role of the preppy who rats out Chris O Donnell in Scent of a Woman — an act of betrayal for which a generation of cinemagoers remains eternally grateful. Leonine, entitled, freckled, boorish, Hoffman’s bully seemed to own the air breathed by others. It was this performance that caught the attention of director Paul Thomas Anderson who was to cast him in Boogie Nights, Magnolia, and Punch-Drunk Love, playing exactly the kind of pudgy self-haters George Willis jr would have rounded on mercilessly. It is almost as if Hoffman were playing his own tormentor.
Boogie Nights (1997) — Scotty
As the chubby boom operator in Anderson’s porno epic, Hoffman bulged from his t-shirts, a fatso in a sea of perfect bodies, ruinously in love with Mark Wahlberg’s blithely indifferent stud. Together with his role as sex pest in Todd Solendz’s Happiness (1998), his gut overhanging his underpants, it established Hoffman as Hollywood’s leading masturbator-in-chief. Almost unwatchably private, his flesh luminous with self loathing, these performances nonetheless amounted to the boldest of self-proclamations — a talent daring itself into the open, like a bashful streaker.
Flawless (1999) — Rusty Zimmerman
Joel Schumacher’s buddy movie about a cop recovering from a stroke (De Niro) who takes singing lessons from a local drag queen (Hoffman) is formulaic filmmaking without formula’s fun. De Niro is so dour he barely registers, maybe sensing that this was Hoffman’s show, his first leading role, and the first to uncover his feminine, feline grace. He moves as if on ball-bearings. Drag queen roles are a gift to an actor — it’s a performance-within-a-performance — and they were everywhere in the 1990s, but for Hoffman it’s the off-moments that are most revealing, as when Rusty returns fire to bellow expletives at a retreating De Niro. Beneath the sequins and pearls, he locates a survivor’s weary toughness.
The Talented Mr Ripley (1999) — Freddie Miles
Hoffman’s first outright theft of a movie. Anthony Minghella’s adaptation of the Patricia Highsmith thriller featured a toasty enough cast — Jude Law, Matt Damon, Gwyneth Paltrow — but Hoffman is as sly and insinuating as smoke as the rich wastrel Freddie Miles who rolls up in Rome and instantly smells a rat about Ripley. “How's the peeping, Tommy?” he badgers, “how's the peeping?”, as maddeningly cheerful a tormentor as Peter Sellars’s Quilty in Lolita. It was this role that first drew Meryl Streep’s attention. “This actor is fearless,” she noted. “He’s given this awful character the respect he deserves, and he’s made him fascinating.”
Almost Famous (2000) — Lester Bangs
Cameron Crow’s soft-hued rock-n-roll memorabilia album feels a little over-praised these days — a throwback to the time when Kate Hudson was Hollywood’s latest crush and Crowe was supposed to be the new Billy Wilder; but Hoffman still pops as the ornery, caffeinated rock critic Lester Bangs. “You got here just in time for rock n roll’s death rattle,” he informs his young protogee. “There’s nothing about you that's controversial." Much could be said of the movie, but Hoffman’s ease switching between the most rambunctious extroverts and featherlite introverts was now apparent.
Capote (2005) — Truman Capote
Tobey Jones portrayal of Truman Capote in Infamous (2006) was the finer act of mimicry, but Hoffman’s was the greater performance, which tells you something about movie acting. Hoffman shed many pounds, reigned in his movements, and raised his usual baritone an octave to get Capote’s babyish goosequill voice, but having taken his fill of Truman, he then empties himself again — he makes his Capote a listener, a highly manipulative empath, drawing others out of themselves with a crocodile’s patience and cunning. He won an Oscar for Best Actor; surprisingly perhaps, for the academy like their geniuses hot. Bennett Miller’s film is grave, bone-dry, funereal; at the end, Capote sips Martinis as if readying himself to slip beneath their surface in for good.
Charlie Wilson’s War (2007) — Gust Avrakotos
Hoffman is almost illicitly enjoyable in Mike Nichol’s comedy about covert war in Afghanistan. Playing a CIA bureaucrat with a sagging gut, smoked spectacles, and the kind of thick, handlebar mustache found only on true commie-haters, he fires off Aaron’s Sorkin’s dialogue as if belching smoke. He’s so beautifully fulminous he almost unbalances the movie, were it not for the comic rhythm he and Tom Hanks finds together. “You're no James Bond,” says Hanks. “You're no Thomas Jefferson, either,” snaps Hoffman. “So let's call it even.” The scene in which they first meet in the congressman’s office, Hanks dodging the calls of a circling press, is a door-slamming farce unto itself.
Doubt (2008) — Farther Brendan Flynn
Few actors could have balanced the demands made by John Patrick Shanley’s drama about a Catholic priest accused of molesting one of his pupils, which requires that we must believe equally in his innocence and, at different times, the possibility of his guilt. The film, which Shanley adapted from his own play, is a little too pleased with this central ambiguity than it ought to be but the film lives through its performances. Maybe a few years earlier, we might have tipped too readily towards believing Hoffman capable of perversity — he had, after all played a disgraced preached in 2003’s Cold Mountain — but its funny what Oscars can do for an actor: freshly garlanded, Hoffman brought newfound probity to the part.