There are precious few actors who can truly be called chameleons, and the late great Philip Seymour Hoffman was one of them. An uncannily accurate performance in Capote won him the Academy Award for Best Actor, but going through the man’s filmography makes one think he could’ve (and should’ve) won more. His talent was of the highest order, and Hoffman’s greatest movies demonstrate how he commanded attention in roles large, medium, and small. Easily one of the most phenomenal actors of his generation, Hoffman’s presence alone makes a movie worth watching.
Philip Seymour Hoffman was in many reputable works and always made them better. Though some can be on the heavier side (Doubt) or the quirkier side (Punch-Drunk Love), Hoffman has been in many movies that are easy to rewatch several times over. Not all of Hoffman’s most rewatchable projects are necessarily his best, but they’re highly entertaining, move at a compelling pace, and show Hoffman’s amazing versatility in a variety of genres.
10 ‘Along Came Polly’ (2004)
Directed by John Hamburg
The moment that Sandy Lyle (Hoffman) walks through that door in a tuxedo and announces that the best man is “in the house” before immediately taking a nasty fall onto that waxed hardwood floor, the audience knows they can expect a hilarious performance. A camera crew is following Sandy around to do a documentary about him, and the viewer can tell pretty quickly that this washed-up actor has comically more ego than talent.
Despite its formulaic plot, Along Came Polly has plenty of laughs and strong performances. Ben Stiller and Jennifer Aniston are solid as the unlikely pair, and Alec Baldwin plays another very funny side character. That said, Hoffman steals every scene he’s in. Thanks to him and phrases like “rain dance” and “white chocolate,” this romantic comedy boasts one of the funniest basketball scenes in movie history. Is this a classic? No, but Sandy is playing Judas in a small production of Jesus Christ Superstar and tries to steal all of Jesus’ lines. This wildly self-centered character elevates an otherwise mediocre movie — that alone deserves dozens of repeated viewings.
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9 ‘The Talented Mr. Ripley’ (1999)
Directed by Anthony Minghella
Image via Miramax
Based on the novel by Patricia Highsmith, The Talented Mr. Ripley is about a young pianist named Tom (Matt Damon) who is paid a large amount to bring a playboy named Dickie (Jude Law) back from Italy in the 1950s. Philip Seymour Hoffman plays the playboy’s buddy Freddy in an excellent supporting performance where every line is delivered so well, including “Tommy, how’s the peeping?”
Filmed largely in Italy, the scenery outside is so gorgeous that it’s sure to make the viewer want to take a vacation there. Jude Law, Matt Damon, and an arguably never-better Gwyneth Paltrow are at the top of their game. Hoffman, who is always at the top of his game, doesn’t have a lot of screen time here, but he makes every second count, as he plays the obnoxious rich guy as well as anybody out there. Hoffman is confident and full of life and bravado, quickly becoming one of the film’s scene-stealing characters.
The Talented Mr. Ripley
Release Date December 25, 1999
Runtime 139 minutes
Writers Anthony Minghella
8 ‘The Master’ (2012)
Directed by Paul Thomas Anderson
image via The Weinstein Company
The Master is an incredible drama about a very troubled loner, WWII veteran, and dangerously good drink mixer named Freddie (an electric Joaquin Phoenix). In search of purpose, he gets pulled into a cult based in part on Scientology during the 1950s. Writer-director Paul Thomas Anderson has called The Master his favorite of his works so far, and it’s not hard to see why: the immersive direction, the emotional intensity, the eccentric characters. It takes a heck of a personality to tame Freddie and a powerful actor to truly stand toe to toe with Phoenix’s furious and nuanced craft.
Enter Philip Seymour Hoffman, who plays the leader of a cult that spews nonsense about “de-hypnotization” and other things with the remarkable confidence and charm that can effortlessly fool many people. It is so enthralling to watch him, perhaps best encapsulated in the scene when he indoctrinates Freddie by asking him deeply personal questions while telling him he’s not allowed to blink. The conflicted and sometimes funny relationship these two have will likely pull the viewer back into watching the endlessly fascinating The Master again and again.
The Master
Release Date September 7, 2012
Runtime 137 minutes
Writers Paul Thomas Anderson
7 ‘The Ides of March’ (2011)
Directed by George Clooney
Image via Sony Pictures Releasing
Directed by George Clooney, The Ides of March has a similar base-driven score as the one in House of Cards, which both informs the tone and emphasizes the quick pace of a political thriller. Ryan Gosling plays a campaign press secretary who tries to protect both presidential candidate Governor Mike Morris (played by Clooney) and himself during the Democratic Primary. For those in the mood for a relatively dark and realistic look at the political hustle, The Ides of March doesn’t disappoint.
Based on a play by Beau Willimon, the film is packed with stars besides Hoffman, Clooney, and Gosling: Evan Rachel Wood, Paul Giamatti, and Marisa Tomei are all exciting to watch. Not the least of which is Hoffman, who plays the governor’s loyalty obsessed campaign manager. The importance of every single detail and the emphasis on how quickly things can turn (in or out of one’s favor) make this movie easy to watch more than just once.
6 ‘Boogie Nights’ (1997)
Directed by Paul Thomas Anderson
Image via New Line Cinema
Paul Thomas Anderson’s breakout movie is crafted so well that it remains one of his best. As in all his work, the acting in Boogie Nights is top-notch for every member of this large cast. For his part, Philip Seymour Hoffman plays a guy named Scotty who’s in love with porn star Dirk Diggler (Mark Wahlberg), an affection that will never be reciprocated. Scott’s awkward attempt to kiss Dirk is so desperate that it’s even comical at first. But, in the wake of the misfire, it’s heartbreaking to watch Scotty alone in his car.
Hoffman doesn’t even need to say anything to captivate the audience. Notice how Paul Thomas Anderson places him right next to Wahlberg during Diggler’s big fight with Jack (Burt Reynolds). His body language (like how he places his arms) gradually expresses more and more concern for his crush. Hoffman is by no means the main star of Boogie Nights, but this very funny, tragic, and moving drama shows, as well as any other, that he can play a side character like it’s nobody’s business. Small yet vital parts like Hoffman’s make Boogie Nights such a fascinating exercise that invites a rewatch if only to see what more one can discover from this complex tapestry of human emotion.
Boogie Nights
Release Date October 7, 1997
Runtime 155
Writers Paul Thomas Anderson
5 ‘Almost Famous’ (2000)
Directed by Cameron Crowe
Image via DreamWorks Distribution LLC.
Directed by Cameron Crowe, Almost Famous focuses on the experiences of an aspiring rock n’ roll journalist who goes on tour with the fictional band Stillwater. Occasionally, this young man will talk to Lester Bangs (Hoffman), an already-established music critic who dislikes Jethro Tull’s Thick as a Brick and takes Jim Morrison for a drunken buffoon. His most playful scene is when he goes on a rant at a radio station, puts on Iggy Pop at an earlier hour than one might be used to, and starts to dance.
Meanwhile, Lester has other tokens of wisdom for the young protégé who keeps sending him work. He makes it clear that he cannot make friends with rock stars, as they just want him to write about them positively. The final half-hour aside, Almost Famous often veers too far into romanticizing a problematic era. Thus, Lester’s insistence on being unmercifully honest is very important to balancing that out a little. Hoffman plays a small role, but he’s one of the biggest reasons why this movie is so rewatchable — him and the movie’s all-time great soundtrack.
Almost Famous
Release Date September 22, 2000
Runtime 122
Writers Cameron Crowe
4 ‘Mission: Impossible III’ (2006)
Directed by J.J. Abrams
Image via Paramount Pictures
Mission: Impossible III begins with a scene so alarming that the viewer knows that whoever Philip Seymour Hoffman plays is a force to be reckoned with. It turns out he’s a black market trafficker named Owen Davian, and watching him count to ten is genuinely scary. From the start, he looks like a strong challenge to Ethan Hunt (Tom Cruise), and his character doesn’t disappoint. Even though the movie is directed by J.J. Abrams, the plot is pretty easy to follow: a now-engaged Ethan comes out of retirement to find his former mentee, Agent Lindsey Farris (Keri Russell), and bring her back.
With a helicopter chase in a wind farm, an amusing argument in Italian, an infiltration of the Vatican, a bridge that takes a beating, a pre-Breaking BadAaron Paul out of nowhere, and more, Mission Impossible III has lots of details that merit a rewatch. Like many great movies, M: I III had a wild development history, but this third installment brought the Mission Impossible franchise back after a 6-year hiatus — and fans currently awaiting the eighth entry are grateful for it.
Mission: Impossible III
Release Date May 5, 2006
Runtime 126 minutes
Watch on Paramount+
3 ‘Charlie Wilson’s War’ (2007)
Directed by Mike Nichols
Image via Universal Pictures
In Charlie Wilson’s War, Philip Seymour Hoffman gets some dark hair, a cool mustache, and even cooler glasses to play Gust Avrakotos. Set in 1980, this historical film has enough cocaine, jacuzzis, and music to make Cold War politics very easy to sit through. Other cast members, including Tom Hanks, Amy Adams, Julia Roberts, and Emily Blunt, make for a star-studded cast who each give eye-catching performances that help to make this one of the best war comedies of the century.
Gust is blunt, loud, and somewhat lacking in diplomatic skills. For example, he tends to break his boss’s window out of rage. Hoffman is very funny and charismatic in this role, which earned him an Oscar nomination for Best Supporting Actor. The New York Times even calledCharlie Wilson’s War “more of a hoot than any picture dealing with the bloody, protracted fight between the Soviet Army and the Afghan mujahedeen has any right to be.”
Charlie Wilson’s War
Release Date December 19, 2007
Runtime 102 minutes
Writers Aaron Sorkin , George Crile
2 ‘The Big Lebowski’ (1998)
Directed by The Coen Brothers
Image via Gramercy Pictures
Joel and Ethan Coen made one of the most psychedelic neo-noirs with what is now a cult classic, The Big Lebowski. When the Dude (Jeff Bridges) gets himself involved in finding the wife (Tara Reid) of a man with the same name as him, he shows up at the mansion. There, he runs into Mr. Lebowski’s assistant, played by Hoffman, whose demeanor convinces the viewer of the setting more than the ostentatiousness ever could.
Bridges and John Goodman are the main showcases here, but Hoffman does an excellent job as the wealthy assistant. His response to Bunny’s forward offer to the Dude is so good, as he tries in vain to keep some air of respectability around here. Hoffman’s small but memorable performance adds an extra layer of decadence and humor to a mansion that tries to keep up appearances in the face of disaster. He helps make The Big Lebowski one of the Coen Brothers’ most hysterical comedies, not to mention a rewatchable gem that never gets old.
The Big Lebowski
Release Date March 6, 1998
Runtime 117 minutes
Writers Ethan Coen , Joel Coen
1 ‘Moneyball’ (2011)
Directed by Bennett Miller
Image via Sony Pictures Releasing
One of the best movies about perfection, 2011’s sports drama Moneyball tells the story of Billy Beane (Brad Pitt) and his attempt to reshape the Oakland Athletics for a memorable 2002 MLB season. This movie is a lot of fun to watch for many reasons, and of course, Philip Seymour Hoffman is one of them. As the Athletics’ manager Art Howe, his resistance to Beane and Peter Brand’s (Jonah Hill) obsessive philosophy underlines how ridiculous it sounded to everyone around them.
When Beane tells him that a player’s fielding doesn’t matter and Howe says he’s “heard enough of this conversation,” the viewer doesn’t blame him. Hoffman carries himself so naturally here that viewers can sense how angry Howe is without him raising his voice or exuding aggressive body language. The exasperation on his face and the way he breaks eye contact mid-conversation are more are enough to communicate his animosity. Moneyball is one of the most entertaining sports movies of the 2010s, and it’s always both fun and emotionally engaging to rewatch.
Moneyball
Release Date September 23, 2011
Runtime 133 minutes
Writers Steven Zaillian , Aaron Sorkin , Stan Chervin , Michael Lewis
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