February 3, 2014 6:35PM ET

9 Overlooked Philip Seymour Hoffman Performances

No modern actor was better at making you feel sympathy for the dull, delusional and degenerate

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Philip Seymour Hoffman, one of the most respected film and stage actors of his generation, passed away Sunday at the too-young age of 46. Hoffman transitioned effortlessly from subtle indies to big budget fare, and the majority of his 63 film and television credits were lauded by audiences and critics alike. Nominated for three Academy Awards, Hoffman won Best Actor for his portrayal of journalist Truman Capote in 2005. On stage, Hoffman nabbed three Tony nominations for a variety of roles, most recently in 2012 for his starring turn in the acclaimed revival of Arthur Miller’s Death of a Salesman. At the time of his death, Hoffman was in the midst of filming a spot in The Hunger Games, and speculation is already brewing about what will come of his part. Throughout his career, Hoffman expertly embodied dozens of memorable characters. Here are nine often overlooked roles. —Rob LeDonne

Born and raised in New York, Hoffman caught the acting bug in high school and later attended New York University's Tisch School of the Arts, where he earned a B.F.A. in Drama in 1989. Following graduation, the struggling actor secured his first on-screen credit in a 1991 episode of of Law & Order. He later appeared in a variety of small roles, including a part alongside Al Pacino and Chris O'Donnell in 1992's Scent of a Woman. Here in one of his early films, he plays a bat-wielding bully in the fluffy 1993 Disney comedy My Boyfriend's Back.

For his work in 1999's Flawless, Hoffman was nominated for his first Screen Actor's Guild Award. Playing opposite Robert DeNiro, he portrayed Rusty Zimmerman, a flamboyant but loveable drag queen. While not a box office success, Hoffman's critical accolades continued to build on his status as a respected actor.

Rightly realizing that their collaborations (Boogie Nights, Magnolia) all-but-guarentee critical catnip, director Paul Thomas Anderson teamed up with Hoffman again for Punch-Drunk Love. In this memorable scene, Hoffman has a testy conversation with his co-star, Adam Sandler.

Based on Richard Russo's Pulitzer Prize-winning novel of the same name, Empire Falls aired over two late-May nights on HBO in 2005. With a packed cast that included Paul Newman (in one of his last roles), Hoffman once again stood out and scored his first Emmy nomination. Newman wound up taking home the prize, which didn't faze Hoffman since Newman was his admitted idol. "You want to grow up and be like him, to take his example and learn from it," Hoffman told New York magazine following Newman's passing in 2008. "He was so giving with art and life, and he connected the two, creating something that nobody does or has done."

In one of his rare forays into summer blockbuster territory, Hoffman plays Owen Davian, the foil to Tom Cruise's heroic Ethan Hunt. Like most roles he embodied, Hoffman brought layers and nuances to what would have otherwise been a cookie-cutter character. Even the way he acts against himself in this clip is captivating.

In 2008, Hoffman continued his streak of working with acclaimed directors by starring in Charlie Kaufman's strange tale of an eccentric theater director. Starring opposite Catherine Keener, the film made it onto over 100 Best Films of 2008 lists. "It's exhilarating and exasperating in equal doses," Peter Travers wrote in his Rolling Stone review. "[And] Philip Seymour Hoffman creates a mesmerizing portrait of the artist as a young, old and middle-aged man."

Throughout most of his filmography, Hoffman was typically surrounded by heavyweights as a supporting actor. But for Capote and Pirate Radio four years later, he finally had films to call his own. Alternatively titled The Boat That Rocked, Radio centers on a disc jokey battling censorship in the sixties.

In the acclaimed drama Moneyball, director Bennett Miller rounded out his cast with Brad Pitt, Robin Wright and more of Hollywood's most respected actors. Despite going toe-to-toe with Pitt, Hoffman once again shone in the ensemble. Playing Art Howe, the real-life manager of the Oakland A's, didn't net Hoffman any awards. But it did help nab the film an Oscar nomination for Best Picture.

For George Clooney's taut political thriller, Hoffman once again scored rave reviews. Hoffman and [Paul] Giamatti remind you of just how good they are," wrote Peter Travers, "digging into the script's choicest dialogue." In this scene, he attempts to school co-star Ryan Gosling on the art of dirty politics, expertly balancing his emotions between tough and sympathetic.