Five years since the passing of Philip Seymour Hoffman, we look back at the career of the gone much too soon actor. Hoffman had a plethora of memorable acting credits, but here we highlight a few of our favorites and emphasize his incredible range from comedy to drama, from starring to supporting roles, over the course of his lengthy career.

Twister (1996)

By Kevin Jones

Philip Seymour Hoffman was an actor who appeared in many highly acclaimed films about serious subjects with top-notch directors. But, in lieu of discussing any of those, I want to talk about Twister. It was not his most refined film or even his best performance, but it is one that I think about the most in the years since his death. His appearance as Dusty, the manic, thrill-seeking, and enthusiastic tornado chaser, proves infectiously energetic. As he hypes up the actions of Bill “The Extreme” Harding (Bill Paxton) or whoops and hollers as they head into the heart of a tornado, Hoffman chews scenery like few other actors could. It is certainly a silly movie, but it finds Hoffman in one of his most out-of-the-box appearances and at his most joyously insane. It is a great demonstration of the possibilities when an actor puts aside any of their prejudices or reservations over how “serious” a film is, instead just embracing the character. He was very rarely given the chance to play this type of character, but it highlights both his incredible range and his willingness to commit entirely to whatever role he found himself playing.

Boogie Nights (1997)

By Matt Schlee

Boogie Nights falls in an array of standout supporting roles by Hoffman. Among an absolutely star-packed cast, Hoffman manages to set himself apart as Scotty J., the desperate and clinging admirer of protagonist and celebrity newcomer in the pornography world, Dirk Diggler (Mark Wahlberg). Hoffman’s performance is light but also brings a sincerity and a tragic slant to a character that might’ve been wrongly played with comic relief by a lesser actor. He makes a lot of very limited screen time, playing the focal point in some of Boogie Nights‘ most memorable moments. The film was one of several collaborations with Paul Thomas Anderson who was one of Hoffman’s biggest fans, and while his role in Boogie Nights is not a large role, it’s a truly impactful one.

The Big Lebowski (1998)

By Matt Schlee

Another supporting character for Hoffman, his performance as Mr. Lebowski’s right-hand man Brandt in the Coen Brothers‘ The Big Lebowski is perhaps Hoffman’s funniest moment. The goofy and ceaselessly loyal assistant to the wealthiest man in town has fantastic rapport with Jeff Bridges. The back-and-forth between the pair as Brandt tries to relate to The Dude in what he perceives as common-man’s language is subtly hilarious and his attempts to respectfully explain the deviant behavior of his employer’s wife show Hoffman’s pension for silliness which came out with far too little frequency throughout his career.

25th Hour (2002)

By Ben McDonald

One of the more underappreciated roles of Philip Seymour Hoffman’s career is found in Spike Lee’s 25th Hour, a chilly portrait of post-9/11 New York City in which the actor plays high school English teacher Jacob Elinsky. 25th Hour follows Montgomery Brogan (Edward Norton) across his last day of freedom before being sent to jail for felony drug dealing, as he spends his final hours getting drunk at bars with Jacob and another childhood friend (Barry Pepper).

During all of this, Jacob is undergoing his own personal dilemma. One of his attractive young English students (Anna Paquin) has snuck into the bar and is hitting on him (or so he believes). Jacob knows she is underage, and it would be profoundly immoral to make a move on her, but he is just drunk enough to give in to the impulse. He momentarily concedes his self-control and kisses her in the bright red bathroom of the nightclub, but she rejects him with a stunned stare. It’s a hypnotic scene of direction from Lee, but also a masterclass of acting from Hoffman- we understand his emotions every step of the way, from hopeful lust to embarrassed disgust.

Jacob’s history isn’t ever explicitly explained, but Hoffman conveys all we need to know entirely through his drunken body language and stuttering sentences. And speaking of drunken performances, Hoffman legitimately delivers one of the most believable depictions of intoxication I’ve ever seen in film. He doesn’t overact or histrionically slur his words, but the gradual parabola of his unfocused gaze convinces one immediately of his inebriation. As Roger Ebert shrewdly observes in the closing paragraph of his review,

I’ve seen a lot of people drinking in a lot of movies. I’ve seen them sobering up the morning after. But I don’t remember anyone starting out sober, getting drunk, and then returning to sobriety quite like Hoffman does it here. We know exactly where he’s at during these transitions, but we never see them happening.

Punch Drunk Love (2002)

By George Morris

A relatively small role in the grand scheme of things but with a hefty impact, Hoffman portrays Dean the Mattress Man in Paul Thomas Anderson’s powerful comedy drama. Hoffman has a knack for playing seedy characters, and his ‘legitimate businessman’ who also runs a sexline perfectly encapsulates his greasy screen presence. Locked into a machismo-battle of wits with Adam Sandler’s Barry Egan, Dean’s status and power is only skin deep, he knows that if it ever came to a throw-down he’d buckle under the pressure. Sandler’s Barry is truthful and deep, the exact antithesis of Dean, who screams profanities over the phone and kicks up a fuss at the slightest sign of trouble.

It’s the intimidation that he suffers when Barry declares the power of his love that really shows the third dimension to Dean’s character. For a man who runs a service built off the pleasures of relationships he’s astounded and rendered helpless by the supposed connection he’s trying to sell. It’s another performance from Hoffman that strengthens what would otherwise have been a two-dimensional side character.

Mission Impossible III (2006)

By George Morris

A distinctively odd choice for such a prominent character actor to appear as the antagonist in JJ Abrams’ Tom Cruise-led action sequel, but for many this was probably their first look at Hoffman’s powerful screen presence. The opening scene alone, which introduces us to Owen Davian, a ruthless arms dealer is pure tension through and through. His blase exterior and lack of concern for Cruise’s Ethan Hunt is a terrifying screen presence. Effortlessly dishing out deaths one after another, he remains the series’ best antagonist (possibly bested by Sean Harris’ later turn as Solomon Lane).

There’s an underlying brutality to Mission Impossible III which is absent from the other films in the series. It’s more ruthless and unforgiving in its approach to character and violence. By association, a lot of this seems because of Philip Seymour Hoffman, who refuses to give in to the grandiose and theatricality of typical action villains and instead opts for a softer, slower and more meaningful approach. There’s no fist fights and car chases with him. Instead just a chair, some rope, and maybe a monologue or too. And to be honest… more often than not it works better.

Synecdoche, New York (2008)

By Ben McDonald

It’s perhaps a bittersweet coincidence of film history that a mere six years before his tragic passing, Philip Seymour Hoffman starred in Charlie Kaufman’s poignantly surreal meditation on death, Synecdoche, New York. As self-absorbed and impossibly hypochondriac theater director Caden Cotard, Hoffman delivers one of the finest performances of his career, bringing a striking degree of empathetic relatability to his character that few other actors of our generation can quite match. Synecdoche, New York begins with Caden in his forties, suffering from constant intrusive thoughts that he has a life-threatening disease. Caden feels that his life is on the brink of slipping away, and begins work on his magnum opus by converting an impossibly vast warehouse into a surreal theater-simulation of his life. We follow Caden throughout his midlife and into the final years of his life, watching as his unhealthy obsession with death collapses in on itself, contradicting basic truisms of reality and blurring the line between his art and his life.

Hoffman, under the weight of meticulous makeup that convincingly depicts the physical erosion associated with aging, imbues every inch of his performance with a teary fatalism. Inferring through interviews about the role, it’s clear the late actor understood exactly what Kaufman was doing in Synecdoche and what it required of him throughout. Hoffman conveys Caden’s exhaustion throughout the film to a T, depressively wallowing in the certainty of his demise rather than celebrating the time he does have left. The final moments of Synecdoche, New York are some of the most magnificently moving in all of 21st century cinema, anchored just as strongly by Hoffman’s heartbreaking performance as they are by Charlie Kaufman’s masterful direction and script. Knowing that Hoffman died less than a decade after Synecdoche, New York makes the film an especially raw viewing now, but also adds a profound immediacy to its timeless message that life is a brief gift well worth cherishing.

The Master (2012)

By Alex Sitaras

If I knew Paul Thomas Anderson, I would’ve said that he directed The Master with me in mind. The film stars two of my favorite actors, Hoffman and Joaquin Phoenix, and wrestles with a number of universal themes such as confronting one’s past, free will, and the subjectivity of truth. Hoffman plays Lancaster Dodd, the leader of a religious movement called “The Cause”, who travels across the United States in hopes of recruiting followers for his religion, one that has drawn a number of comparisons to Scientology. He encounters Freddie Quell, a World War II veteran who is traumatized from his time abroad, and takes a strong liking to Freddie (some have regarded the friendship between the two as homoerotic). Given Freddie’s mental illness, Dodd has in him a subject that he may easily manipulate and is malleable to illogical strains of thought. Even so, Dodd remains immensely likable to Freddie for much of The Master’s duration, Freddie often resorting to violence to protect Dodd’s character and to confront skeptics of The Cause.

Philip Seymour Hoffman is immense in his role in The Master– very few actors could take a character as repulsive and make him seemingly charming. Hoffman’s portrayal of Dodd helps illustrate just how well senseless fervor can take hold in cults and amongst followers of populist leaders. The Master illustrates this aspect of the human condition that seems incontrovertible, as it is ever repeated throughout history despite its appalling nature.