To mark the release of the documentary I Am Heath Ledger, here’s a look at some of the roles that made the Australian-born actor a fan favorite before his tragic death from a drug overdose at age 28:
10 Things I Hate About You (1999)
Ledger made his American feature-film debut in this retelling of William Shakespeare's The Taming of the Shrew as a high school romantic comedy. If a little too inherently nice to play supposed bad boy Patrick Verona, the Aussie oozed plenty of easy charm while bantering with co-star Julia Stiles, and nailed the obligatory show-how-much-you-love-her-in-front-of-the-school scene with a surprisingly impressive rendition of "Can't Take My Eyes Off You."
Memorable Quote: "It's not every day you find a girl who'll flash someone to get you out of detention."
A Knight’s Tale (2001)
Following a turn as Mel Gibson's dutiful son in The Patriot (2000), Ledger went full-blown leading man for this mashup of a medieval underdog story and rock opera. He comfortably donned the hero's mask as squire-turned nobleman William Thatcher, showcasing his steely eyed bravery in competition, poetic touch while wooing the damsel Jocelyn, and an ability to tug at the heartstrings in a tender reunion with dear old dad.
Memorable Quote: "No! I will not run!"
Monster's Ball (2001)
With his minor but memorable role in this unsettling drama, Ledger served notice that he had some serious acting chops to go with a pretty face. As Sonny Grotowski, the youngest in a line of prison guards and abusive parents, he carried the hangdog look of a young man who has already seen too much in life, until erupting in a shocking confrontation with his father.
Memorable Quote: "Well, I always loved you."
Lords of Dogtown (2005)
While Dogtown and Z-Boys (2001) offered the authentic narrative of skateboarding's origins, Ledger's performance was worth the price of admission for this Hollywood-ized version. As surfshop owner and skateboarding patron saint Skip Engblom, the heartthrob disappeared behind a mop of stringy hair, fake teeth and stoner's cadence to steal his scenes. Furthermore, those who knew the real Skip Engblom marveled at how adeptly Ledger captured their old friend's spirit.
Memorable Quote: "Yeah, this is Skip Engblom and the Zephyr Skateboard Team. Here's our entry fees. Now where's our trophies?"
Brokeback Mountain (2005)
It was in this later release from 2005, via the role of repressed gay cowboy Ennis Del Mar, that Ledger made the first of his two seismic impacts on cinematic history. All clenched teeth and bottled-up emotions, Del Mar occasionally succumbed to his feelings for Jake Gyllenhaal's Jack Twist, but otherwise denied them both a chance at happiness until the story's inevitably sad conclusion.
Memorable Quote: "It's because of you, Jack, that I'm like this. I'm nothing, I'm nowhere."
Returning to his native Australian accent, Ledger unleashed the full range of his talents as the lovestruck, heroin-addicted poet Dan Carter. Although the film offered a stock narrative of the destructiveness of drugs, Ledger radiated authenticity from start to finish through the bliss of the high, the crushing agony of withdrawal and a heart-wrenching goodbye to love.
Memorable Quote: "There's no going back. If you're given a reprieve, I think it's good to remember just how thin it is."
The Dark Knight (2008)
Finally, there was his unforgettable performance as Batman's arch-nemesis in this superhero epic. While heavyweights like Jack Nicholson had portrayed the Joker as a cackling, sharp-dressed villain, Ledger's version revealed the remains of the haunted, twisted man behind the scars. It wasn't his final movie – the actor died while filming The Imaginarium of Doctor Parnassus (2009) – but it landed him his lone Oscar, and left a lasting impression of his talent when allowed to unleash his imagination.
Memorable Quote: "You know, you remind me of my father. I HATED my father."