To call Philip Seymour Hoffman one of the most underrated actors of his generation seems like an overstatement, yet such a drastic description applies to Hoffman's performances on-screen. Possessing a fearlessness few actors could rely on, Hoffman tackled his roles with complete dedication, no matter how limited his screen time.

Whether playing the charismatic leader of a cult or appearing in a small cameo as a loudmouthed gamble, Hoffman gave his characters life and believability that transformed them from simple Film characters into living, breathing individuals of startling complexity.

His nearly 25-year-long career — cut short when the actor was in his prime — gave us some of the best, most memorable characters ever to appear on film, and it is doubtful audiences will ever see an actor of such bravery and versatility as Hoffman again.

From his initial start as a supporting cast member to his eventual rise as an Oscar-winning talent in the final few years of his life, here are some of the greatest films to feature the Academy Award-winning actor Philip Seymour Hoffman.

Hard Eight

Philip Seymour Hoffman received his start in the early '90s, appearing in various TV show guest appearances and indie films before taking on supporting roles in films like Leap of Faith and Scent of a Woman. In 1996, after a string of movies that saw him in these supporting roles, Hoffman found himself cast in a promising young director's debut film, Hard Eight.

Hard Eight tells the story of an older, mysterious professional gambler named Sidney (Philip Baker Hall) who takes a young protege (John C. Reilly) under his wing. The two form a successful partnership at first, but their relationship is soon threatened when the protege falls for a cocktail waitress (Gwyneth Paltrow), and an old acquaintance (Samuel L. Jackson) threatens to reveal a dark secret about Sidney's past.

The movie responsible for Paul Thomas Anderson's overnight transformation into a full-fledged directorial talent, Hard Eight proved an immediate success on the indie film scene, propelling Anderson to larger-budgeted projects like Boogie Nights and Magnolia.

In Hard Eight, Hoffman portrays an overeager gambler who antagonizes Sidney at a craps table. The role marked the beginning of a long-lasting relationship between Philip Seymour Hoffman and his eventual frequent collaborator Paul Thomas Anderson.

Boogie Nights

After the success of Hard Eight, Paul Thomas Anderson set out to make an epic character study set looking at various individuals associated with the golden age of adult entertainment in the 1970s. The film — Boogie Nights — featured a huge cast of characters and once again saw Philip Seymour Hoffman team up with Anderson in the second of their five films together.

Eddie Adams (Mark Wahlberg) is a lowly nightclub dishwasher with few professional prospects to rely on. His fortune in life changes, however, when he is discovered by a veteran adult film director (Burt Reynolds), who wants to cast him in his latest movie. 

Like Hard Eight before it, Boogie Nights featured Philip Seymour Hoffman in a minor supporting role named Scotty, a quiet boom operator locked in an unreciprocated romance with Wahlberg's Eddie. As happened to be the case with Hard Eight, Hoffman managed to take an otherwise small role and fleshed it out, making Scotty a fully-formed character who shared some awkward and hilarious scenes where he tries seducing Wahlberg’s lead role.

Almost Famous

By the end of the 1990s', Hoffman rose to career prominence as a versatile actor able to stand out even in the most unremarkable movies (Patch Adams, Twister). At the start of the next decade, Hoffman — still a supporting actor at this point — continued his critical ascent, appearing as the legendary rock critic Lester Bangs in Cameron Crowe's Almost Famous.

Set during the 1970s, a teenage journalist (Patrick Fugit) for Rolling Stone takes on an assignment to write a feature about the up-and-coming rock band called Stillwater. Joining the band as they tour across the U.S., the journalist bonds with the band members and their various groupies, including a mysterious young woman (Kate Hudson) that he eventually falls in love with.

The film may not include Philip Seymour Hoffman's greatest performance, but it still manages to illustrate his strengths as an actor, this time able to embody the real-life personage of Bangs—mannerisms, vernacular, and all. In the film, Hoffman's Bangs—a combative music journalist (in)famous for not holding back on his opinions on what he saw as the deteriorating state of the '70s music industry—serves as a mentor to Crowe's main character. It's an underrated performance in a filmography full of great roles.

Punch-Drunk Love

In 2002, Hoffman joined Paul Thomas Anderson in their fourth collaboration together in the comedy-drama Punch-Drunk Love.

The film stars Adam Sandler as a depressed, unstable salesman named Barry who falls in love with his sister's coworker (Emily Watson). The mutual romance between each other is hampered by Barry's social awkwardness, as well as his involvement with an adults-only phone operator attempting to blackmail him.

In the film, Hoffman plays “The Mattress Man” Dean Trumbell, a mattress shop owner and the “supervisor” of an adults-only hotline line that Barry calls. Though lacking significant screen time, Hoffman takes advantage of every scene he's in, playing Trumbell as the sleazy, dishonest criminal whose bark is a lot worse than his bite.

It’s a short but memorable performance, and one that proved a lot meatier than any role given to Hoffman by Anderson up to that point, serving as a stepping stone from the bit roles in Hard Eight, Magnolia, and Boogie Nights and his later starring role in Anderson’s The Master.

Cold Mountain

By 2003, Philip Seymour Hoffman's rise to prominence reached its final stages, with Hoffman handing in a few last supporting roles before his eventual establishment as one of Hollywood's finest actors. In the case of Cold Mountain, Hoffman appeared as the eccentric Reverend Solomon Veasey in the underrated anti-war film Cold Mountain.

Adapted from the award-winning novel of the same name by Charles Frazier, Cold Mountain tells the story of a Civil War soldier (Jude Law) who deserts his post, journeying across the South to return to his love (Nicole Kidman). Hunted by the Confederate Home Guard, the soldier encounters an assortment of people affected by the war in some way, all the while his romantic interest struggles to support herself with the help of an eccentric but strong-willed local woman (Renée Zellweger).

In the film, Hoffman plays Rev. Veasey, an amoral small-town preacher who assists Law's soldier on his way home, briefly joining him for a short time. He's a vain, shallow man of the cloth who is not above getting drunk or unwittingly putting both his and Law's character's lives in jeopardy, but Hoffman gives him enough eccentricity to make him both repulsive and somehow sympathetic.

Capote

Years of hard work paid off for Philip Seymour Hoffman, with the actor gaining the title in 2005's Capote. Based on the 1988 biography of Truman Capote by Gerald Clarke, the film follows the novelist's efforts to research the 1959 murder of a family on their Kansas farm in an attempted robbery, resulting in Capote's acclaimed nonfiction work, In Cold Blood.

The film served as a major turning point in Hoffman's career, earning him widespread praise for his performance as the famous writer, earning Hoffman the Academy Award for Best Actor (among a slew of other awards like the Golden Globe, the BAFTA, and the Screen Actors Guild Award).

In the film, Hoffman brings the larger-than-life personality of Capote to the screen during a crucial time in the writer's career. Hoffman’s mannerisms, voice, and accent all make audiences feel as though they're observing the actual Capote, not a trace of Hoffman remaining on screen. In an otherwise flawless filmography, it may be Hoffman’s greatest performance.

The Savages

After Capote, Hoffman maintained his leading man status in the years to come, appearing in central roles in films like Mission: Impossible III and Charlie Wilson's War. 

In between those two successful films, Hoffman delivered yet another raw performance in Tamara Jenkins' overlooked dark comedy, The Savages. The film stars Hoffman and his co-star Laura Linney as two estranged, middle-aged siblings who — after years apart — reconnect to put their emotionally abusive father (Philip Bosco) in a home to treat his dementia.

Blending comedy with hard-hitting drama, Hoffman illustrates the effects a troubled childhood could have on a person later in life, giving Hoffman's character an extreme vulnerability that manifests itself throughout his adult life (including an inability to maintain a serious relationship). It's a tense, often gut-wrenching movie, but ultimately hopeful about the future, seeing Hoffman and Linney's characters able to grow past their previous shared traumas, finding a mutual bond that strengthens their relationship.

Charlie Wilson’s War

In 1980, Democratic Congressman Charlie Wilson (Tom Hanks) focuses more on partying than on political matters. After a congressional investigation nearly costs him his job,  his friend and romantic partner (Julia Roberts) encourages him to turn his life around, leading him to join a knowledgeable C.I.A. agent (Hoffman) and launch Operation Cyclone, a program dedicated to helping the Afghan resistance drive the Soviet Army out of Afghanistan.

In Charlie Wilson's War, Hoffman played real-life C.I.A. operative Gust Avrakotos, perhaps the most competent and knowledgable person in the entire movie. Decked out in a loud '80s wardrobe, stringy hair, and a huge Wilford Brimley mustache, Hoffman brings Avrakotos to life, portraying him as a hardworking, scrupulous agent who is perhaps the only one who realizes that to help the Afghan people requires the U.S.'s attention even after the Soviets have left the country. Like every Hoffman film, he's a marvel to watch on screen, managing to even outshine Hollywood heavies like Hanks and Roberts.

Doubt

Hoffman starred in two dramatically different films in 2008, the first portraying the shy, depressed lead character in Charlie Kaufman's directorial debut, Synecdoche, New York, and the second playing opposite Meryl Streep in the psychological drama Doubt. Both films would earn mostly positive reviews, but it’s Hoffman’s appearance in Doubt that critics rank as one of the actor’s finest performances.

Adapted from the Pulitzer and Tony-winning play, Doubt: A Parable, the film focuses on a naive young nun (Amy Adams) at a Catholic elementary school who begins to suspect one of the priests (Hoffman) is taking advantage of a male student. Enlisting the help of a far sterner, older nun (Streep), the two attempt to figure out if the priest is guilty of pedophilia.

The brilliance of Doubt lay both in its central storyline and conclusion (we never actually find out if Hoffman's priest is guilty or not, and we're left just as unsure about his guilt as the two nuns), as well as the performances of the three principal actors.

In the film, Hoffman plays his character almost entirely as a charming, wise, charismatic father figure to the boys. However, there's something underneath this outwardly caring persona, something potentially sinister, with the priest frequently falling back on the bureaucratic hierarchy of the Church when the two nuns investigate him (at one point loudly screaming, “You have no right to act on your own… You answer to us [the Church]”).

Questions as to his character's guild will forever ignite debate, but there's no denying how indelible Hoffman's performance is. Not many actors can hold their own against someone with as much talent as Streep—one of the finest actors currently working—but Hoffman has always managed to thrive off of other actors' performances and again does so here, with each new scene between the two resulting in pure cinematic magic.

The Master

In the fifth and final collaboration between Hoffman and Paul Thomas Anderson, Hoffman appeared in the 2012 film The Master. 

Set in the early 1950s, unstable alcoholic and WW2 veteran Freddie Quell (Joaquin Phoenix) finds himself drawn to a Scientology-esque cult, led by the enigmatic Lancaster Dodd (Hoffman). As Freddie spends time with the group, he begins to learn more about Dodd, each man confronting their own insecurities and attempting to find their place in the world.

As with Streep in Doubt, Hoffman thrived off the performance of Phoenix, each actor building off of each other's energetic acting styles, creating numerous memorable scenes as a result. As Dodd, Hoffman balances the confident, charismatic leader with a more deep-seated uncertainty about his own abilities and religion. In the movie, Dodd asserts his role as a wise believer in his group’s message, yet is just as quick to burst out in angry tirades when questioned about them.

Mission: Impossible III

Mission: Impossible is that rare franchise that only seems to be getting better with time. Heightening the drama and theatricality of its immediate predecessors, the hit spy series only continues to outdo itself with each new installment, starting with its 2006 outing, Mission: Impossible III.

Coming out of retirement, former I.M.F. agent Ethan Hunt (Tom Cruise) returns to the field to combat a dangerous arms dealer (Hoffman) obsessed with acquiring a biological weapon known as the Rabbit’s Foot.

As the film’s main villain, Hoffman gives a magnetic performance as one of the series’ best (and most terrifying) antagonists to date. Maintaining a stony disposition and perpetual grimace, Hoffman’s Davian makes the ideal counterpart to Cruises’ heroic Ethan Hunt. A startling depiction of a complete psychopath, Davian’s threats against Ethan’s life – spoken not out of anger but as a matter-of-fact statement – are enough to send chills down the most hard-hearted of audience members.

Synecdoche, New York

Apart from Paul Thomas Anderson, Hoffman worked with several other influential filmmakers over the course of his career, including the surreal filmmaker Charlie Kaufman. Starring in Kaufman’s postmodern psychological drama, Synecdoche, New York gives yet another memorable performance that provides a film with its main heart and soul.

Suffering from a traumatic personal life, a New York theater director (Hoffman) pours his emotional pain into his latest work, casting surrogates as his family and friends to replicate the outside world.

Earning a polarized response from viewers and critics, Synecdoche, New York earned praise for its originality and criticism for its pretentious atmosphere. Regardless, Hoffman’s performance in the film is nothing short of brilliant, portraying a man who loses everything he holds dear in life, from his family and loved ones to his sprawling professional career.

Magnolia

Magnolia might feature Hoffman in a less prominent role compared to his other collaborations with Paul Thomas Anderson, but that doesn’t make it any less fantastic a part suited to Hoffman’s dramatic strengths.

Over the course of a single day, numerous inhabitants of Los Angeles search for meaning in their personal lives, their stories ranging from a sexist motivational speaker (Tom Cruise) to a child prodigy (Jeremy Blackman) vying for his father’s (Michael Bowen) love.

As the dedicated nurse Phil Parma, Hoffman appears as an angelic protector for Jason Robards’ character. Never casting any judgment on his patient or his deplorable past actions, Phil spends the bulk of Magnolia trying to reunite the fractured Partridge family. Humane and forgiving, he’s one of the most likable characters ever created by Paul Thomas Anderson, marking another successful collaboration between Anderson and his close friend Hoffman.