Heath Ledger

It’s been a decade since the release of 10 Things I Hate About You, a modern-day remake of the classic Shakespeare play The Taming of the Shrew, and the film that launched Heath Ledger onto Hollywood’s radar and placed him squarely in the hearts of teens everywhere. In honor of Ledger’s final performance in The Imaginarium of Doctor Parnassus, take a trip down memory lane as we highlight Ledger’s 10 most memorable performances from earliest to last.

By Elisa Osegueda

10 Things I Hate About You (1999)

In 10 Things I Hate About You, Ledger brought Patrick Verona to life as a rebellious high school teen, known for smoking cigarettes and drinking. When his friends challenge him to “tame the shrew” (Kat, played by Julia Stiles), he finds himself on a pursuit that leads him to an unexpected transformation. Ladies, look out for Ledger’s singing number as he romantically serenades Kat with "Can't Take My Eyes Off You."

The Patriot (2000)

A year after 10 Things, Ledger made a stunning 360-degree turn in The Patriot, costarring with Mel Gibson as ruthless patriots fighting against the British establishment for the people. The Revolutionary War film tells the story of Benjamin Martin (Gibson), a widowed retired war vet with seven children, who has renounced violence--until his son Gabriel (Ledger) is arrested and taken to be hanged.

A Knights Tale (2001)

The medieval adventure focuses on William Thatcher (Ledger), a curious peasant who spontaneously decides to take the place of his deceased employer in a jousting competition. Ledger cleverly saddles up and fools a handful of French bourgeois as he continues to win one joust after another, but the story takes a sudden turn when a rival threatens to expose his true identity.

Monsters Ball (2001)

The Oscar-nominated film Monster’s Ball gave Ledger a dark, vulnerable and meaty role as Sonny, the son of a racist ex-cop Hank Grotowski (Billy Bob Thornton). In this intense, racially charged drama, Ledger brings to life a fragile correctional officer who desperately seeks his father's love. Unable to cope with his father’s estrangement and hatred, Sonny commits suicide before confessing his love for his father.

The Four Feathers (2002)

A tale of honor and redemption, The Four Feathers is an entertaining action-drama. Harry Feversham (Ledger) is a young officer-in-training in the British Army who’s expected to leave to Sudan to battle Muslim insurgents. Upon ethical reservations, Harry decides to resign, but the decision inevitably leads his fiancée and friends to serve him with four white feathers, symbolizing weakness. Determined to redeem himself; he sets off to Sudan and disguises himself as an Arab.

The Order (2003)

Surprisingly, Ledger takes on the role of a priest in The Order, a religious thriller that leads a young, conflicted priest to uncover an ancient Christian order called the Sin Eaters. While the film received mixed reviews, it only proved Ledger’s thirst for thought-provoking roles.

The Brothers Grimm (2005)

The Brothers Grimm did more than just entertain audiences—it also marked the beginning of a close friendship between director Terry Gilliam and Ledger. In this fantasy-comedy, Ledger costars with Matt Damon as two con-artist brothers who go from village to village pretending to defeat mythical creatures. In an unexpected twist, they stumble upon a village that is legitimately cursed, which leads them to come face-to-face with real creatures.

Brokeback Mountain (2005)

2005 also brought us Ledger’s captivating performance in Brokeback Mountain. The film catapulted Ledger into stardom and got him showered with awards and accolades, including an Oscar nomination for Best Actor in a Leading Role. Brokeback Mountain tells the tragic love story between Ennis del Mar (Ledger) and Jack Twist (Jake Gyllenhaal), two men who form a close bond that leads into a hidden relationship of love, passion and deceit.

The Dark Knight (2008)

When director Christopher Nolan granted Ledger the role as Batman’s nemesis The Joker, Ledger decided to re-create the classic villain, living in isolation in a hotel room for a month, formulating The Joker’s voice, posture, and generating a persona unlike Jack Nicholson’s character in Tim Burton’s 1989 film. His inventive and exhilarating performance didn’t go unnoticed: on January 22, 2008, Ledger died from an accidental prescription overdose, but he posthumously received a Golden Globe Award and an Oscar for Best Performance by an Actor in a Supporting Role.

The Imaginarium of Doctor Parnassus (2009)

The Imaginarium of Doctor Parnassus (aka Heath Ledger’s last film) reunited him with director Terry Gilliam once again. Ledger played Tony, a mysterious outsider who joins a traveling show led by Dr. Parnassus (Christopher Plummer), before his sudden death. It was presumed the film would no longer finish its course, but with the help of three of Ledger’s close friends—Johnny Depp, Jude Law, and Colin Farrell, who stepped in to finish Ledger’s role—audiences can now enjoy Heath Ledger’s last performance.