Heath Ledger’s career lasted a mere fifteen years before he died prematurely at the age of 28. Despite his youth and short-lived time in the spotlight, the actor left an indelible mark on Hollywood, performing in a series of leading and supporting roles that won the hearts of audiences and made him one of the most celebrated young actors of his time.

Ledger had an incredible range as an actor. He played the high school bad boy, a young war hero, and a psychopathic supervillain in just some of his most iconic roles, delivering amazing performances and some truly unforgettable scenes.

10 “Why So Serious”: The Dark Knight (2008)

The final role of Ledger’s career (or one of the last two) was playing the Joker in Christopher Nolan’s The Dark Knight. This role is the most memorable part of Nolan’s Batman series and is what made the trilogy into a classic.

Fans of the comics know that the Joker’s origin story has always been a mystery, one he even admits to remembering different ways. Ledger’s Joker explained the origin of his Chelsea grin a number of ways, the first of which involved a monologue where he held a knife inside an enemy’s mouth. Joker recounted how his father murdered his mother as he watched, then turned the knife on him, saying “why so serious?” As the story ended, Joker slashed his enemy open. This biting quote was so sharp it became the film’s tagline.

9 Death of Gabriel Martin: The Patriot (2000)

The historical action movie The Patriot was a hit when it came out, despite its many historical inaccuracies and offensive revisionism about race. One reason for the success of the movie was the dynamic between actors Mel Gibson and Heath Ledger, who played Benjamin and Gabriel Martin, a father and son torn apart by the American Revolution, only to grow closer again as they fought alongside each other.

When Gabriel Martin (Ledger)’s new wife was burnt alive with her entire family while locked in a church, the young man rode out to seek vengeance–right into a British ambush. Numb with hatred, he strode coolly through the battlefield, until finally being mortally wounded. His father Benjamin found him lying on the ground and held Gabriel in his arms as the boy bled out.

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8 “Jack f*cking Twist”: Brokeback Mountain (2005)

Ledger starred alongside Jake Gyllenhaal in the romantic drama Brokeback Mountain, a tragic love story about two cowboys whose romance pulled them together and apart throughout the 60s and 70s.

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One scene of particular note featured Ledger’s character, Ennis Del Mar, at home with his wife and kid, when he looked up to see a familiar face outside. “Jack f*cking Twist!” he exclaimed, greeting his old lover. The two men embraced, kissing passionately as they swept one another off their feet. Through the window, Ennis’s wife watched her husband kiss another man with the passion of true love.

7 Seducing Kate: 10 Things I Hate About You (1999)

The 90s were a strange time with strange fads, from pogs to Tamagotchi. One trend featured an abundance of Hollywood movies updating Shakespeare plays. Of all these films, the best was almost certainly 10 Things I Hate About You, a remake of The Taming of the Shrew.

Heath Ledger was the ultimate bad boy, a teenage heartthrob who smoked in his lab class, cored textbooks with power tools, and exploited shallow rich pretty boys for cash. A major part of the first act involved Ledger going out of his comfort zone to seduce the school’s shrewish counterculture girl, Kat Stratford (Julia Styles), immersing himself in feminist classics and even going to an underground club catering to punk femmes, until finally he recruited the school’s marching band in a stunt that won her over.

6 Final Joust: A Knight’s Tale (2001)

A Knight’s Tale is surprisingly underrated. It managed to capture a lot of chivalric life in England during the High Middle Ages with amazing fidelity, even as it engaged in pure fun escapism.

The final joust of the film pitted Ledger’s character, the peasant-born William Thatcher, against the villainous Count Adhemar – who unlike Ledger was born into the gentry and grew up studying how to use sword, horse, and lance. Wounded, Thatcher removed his armor, unable to ride with its weight. A single blow from Adhemar would kill him. Despite this, Thatcher managed to unhorse his opponent, hitting so hard both lances exploded in a burst of splinters.

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5 The Panel Trick: The Dark Knight (2008)

Heath Ledger’s rendition of the Joker remains the greatest live action version of the character to date (and anyone who says otherwise should be laughed at). One iconic scene involved him offering to do a magic trick.

He held a pencil upright on a table. When a thug approached, intent on harming the clown, Joker slammed the other man’s head down on the table, making the pencil disappear…into the man’s skull. It’s a short simple scene, and like the pencil, it will remain lodged in audiences brains for the rest of their lives.

4 Skip Losing the Team: Lords of Dogtown (2005)

The biographic film Lords of Dogtown told the story of several real-life skaters and surfers in San Monica, California during the 70s–a group of real-life people who influenced the culture of boarding all over the world.

Ledger played Skip Engblom, the owner of a board shop, Zephyr, who hired young skaters known as the Z-Boys to represent his business when they competed. Gradually, the young stars realized Skip could not pay them what they felt they were worth. For his part, Skip watched helplessly as the stars he helped create left him to pursue fame on their own.

3 The Poem: 10 Things I Hate About You (1999)

The best scene in 10 Things I Hate About You took place when Kat read a poem aloud to her class. Heartbroken after learning Ledger’s character, Patrick Verona, had been paid to date her, she tearfully listed the things she hated about him, ending with a confession that what she hated most of all was that she still loved him.

To be clear, Julia Styles, not Ledger, stole the show here, but it was a scene that only worked with both of them looking at one another as Styles read her poem.

2 Flowers and a Note: Candy (2006)

Some films on this list are feel-good comedies or escapist action movies. To be clear, Candy is not such a film.

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The movie followed a heroin-addicted poet named Dan (Ledger) and his new lover Candy (Abbie Cornish) as they shared their romance while descending into a spiral of addiction. In one unforgettable scene, Dan returned home with flowers for Candy, only to find she wrote a note on the wall in her own blood: “ONCE UPON A TIME THERE WAS CANDY + DAN.” Dan hurried through the house, panicked, the walls graffitied with her writing, but Candy was nowhere to be seen.

1 “I Want My Phone Call”: The Dark Knight (2008)

Here, two scenes that happen back to back need to be counted together. When Batman finally caught Joker in The Dark Knight, the vigilante interrogated the criminal clown in an intense scene where the Joker revealed that Harvey Dent and his fiancee Rachel Dawes had been kidnapped.

As Batman raced to rescue Rachel, the Joker provoked an abusive police officer, repeatedly asking for his phone call until the cop tried to beat him. Joker then killed the cop and staged a breakout, proving no cell could hold him and that he would ultimately always get the last laugh.

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