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10 Things I Hate About You (1999)
"You’re not afraid of me, are you?" This was Patrick Verona's approach to winning over Katarina Stratford (Julia Stiles). This is followed up by a wink-filled, "Well, maybe you're not afraid of me but I'm sure you've thought about me naked?" He clearly has no idea who he's dealing with. But many other teenagers watching the young Aussie with green-tinted eyes were likely unafraid and possibly imagining him just so.
This teen rom-com, a modern take on Shakespeare's Taming of the Shrew, introduced Ledger to America with a performance of "Can't Take My Eyes off of You" that gives Lloyd Dobler and his boombox a run for its money. Patrick launches a charm offensive on Kat that's similar to the one Ledger was launching on Hollywood with this sweet, confident, funny play on what could have just been a one-dimensional heartthrob. Jake Ryan, anyone?
Ledger isn't just eye candy, he is the ideal boyfriend: a sensitive, misunderstood bad boy who doesn't mind cleaning up your puke and fully encourages your riot grrrl dreams.
The Patriot (2000)
Mel Gibson is the star of this over-the-top American Revolutionary War film by Roland Emmerich, but Ledger is the heart of the movie as Gabriel, the eldest son of Gibson's Benjamin Martin. Gabriel's no longer a child, but as Benjamin tells him, Gabriel is his child, and their relationship grounds the film.
Ledger is an idealistic young American eager to join the ranks of the Continental Army against his father's wishes, and believes he is part of the good fight. He's almost too progressive to be true (and likely was, since many question where Emmerich got his facts for the film). In one scene, Ledger's Gabriel speaks with a freed slave who has been forced to fight, letting him know it will not be in vain.
But, Gabriel grows up throughout the film, becoming a grieving husband who decides he must seek justice for all those he's lost. The slow-motion battle scene that shows Gabriel's focus on Colonel Tavington (Jason Isaacs), who has not only killed his wife, but his young brother, is the true climax of the film. It's a dance as they attempt to strike each other down. But it's the naive Gabriel who is taken down with one unexpected blow.
As he lays in his father's arms, he apologizes for everything he has done with his last labored breaths. If you're not already bawling over Ledger's delivery, Gibson's on-screen tears will certainly have you shedding very real ones of your own.
Monster's Ball (2001)
Like Leonardo DiCaprio before him, Ledger had no interest in becoming a teen heartthrob, which he made very clear with this supporting role in the gritty indie drama. Ledger only appears in the first 40 minutes of the film, but his presence hangs like a black cloud over the entire movie.
Ledger plays Sonny, a Georgia prison guard who suffers at the hands of his father, played by Billy Bob Thornton, a racist, hateful, hardened corrections officer who refuses to love his son. It's why Sonny chooses to find love and support elsewhere, often putting him at odds with his dad. Sonny hires a prostitute, who he kindly asks to dinner, comforts a death row inmate against his father's orders, and becomes friends with two young Black boys, who his dad threatens to shoot if they ever step on his property.
One glimpse into Sonny's droopy eyes, and it's clear he has nothing left to give. Ledger does this with few words, letting his crumpled body quietly tell Sonny's sad story. He's the one character in this brutal film that you hope will find a way out — and he does, just not the one you wish for.
Ledger's final scene is also his best — possibly of his career — as you watch him turn the tables on his dear ol' dad, only to show he didn't have that same hate running through his bloodstream. Gun in hand, Sonny asks his dad if he hates him, to which he answers yes. "Well, that's too bad," Ledger says pointing the gun at his heart. "Because I always loved you."
Lords of Dogtown (2005)
After a string of flops — The Four Feathers, The Order, Ned Kelly — Ledger returned with this small but memorable role in the Catherine Hardwicke film, which looks at the rise of the Venice skateboarding scene in the 1970s.
Ledger plays Skip Engblom, the real-life creator of the legendary skating crew the Zephyr Skate Team, nicknamed the Z-Boys, which featured Stacy Peralta, Tony Alva and Jay Adams. Engblom was a board designer and store owner who sold the polyurethane skateboard wheels that allowed these guys to do the same tricks on land that they had been doing in the water.
With bleached blonde hair, bunny teeth, a paisley shirt or two, and a surfer dude accent, Ledger wholly transformed into Engblom. Some thought it was a hammy performance, but for those who knew Skip, it was just Ledger paying attention to the details. "He's almost eerie in how precisely he nailed not only the mannerisms, cadence, and physical presence of Skip," L.A. Weekly's Joe Donnelly said after Ledger's death. "But also how he raises Skip's spirit."
Ledger is the most interesting part of the movie, and in fact, when he's not in it, the energy of the film wanes. The most memorable scene is also the saddest, when we see the downfall of Skip, who has lost his shop and is working for someone else.
In the backroom as he sands down boards, he takes a swig of his whiskey and sings Rod Stewart's "Maggie May" like a man whose got nothing else to lose. And maybe that was Ledger's thought when he took the part, too. Instead, it showed he wasn't just some flash in the pan, but an actor who did a lot by doing very little.
Brokeback Mountain (2005)
Jake Gyllenhaal's "I wish I knew how to quit you" is the most quoted line from Ang Lee's drama about two ranch hands from Wyoming, who fall in love before society is ready to accept them. But that may only be because Ledger's character, Ennis Del Mar, is a man of very few words. Ledger played the more stoic of the two characters, who barely opens his mouth to express himself, and even when he does, it's really more of a mumble. His quiet nature is even a joke in the film, with Gyllenhaal's Jack Twist noting that it took Ennis months to say more than a few grunts. "That's more than I've spoke in a year," Ennis replies. But it's Ennis' quiet journey that we follow.
He's not a martyr, but simply a troubled man who can't deal with who he is. He lies, cheats, and hurts the ones he loves, or maybe just those who love him — Jack, his first wife Alma, his girlfriend Cassie. But you feel for him as you watch him mourn his lover, trying to commit to memory Jack's scent as he breathes in the plaid shirt that Jack would wear up in Brokeback Mountain all those years ago. It was the one place where Ennis could be himself.
Ledger's performance, which he would later say was inspired by an uncle of his, who was gay but also homophobic, is quiet and subdued. It's insular and restrained. You see him change, but it happens quietly. There's no explosion, no epiphany moment. That's why it's easy to forget what Ennis says after Jack shouts his "quit you" line: "Why don’t you?" This exchange really gets at the heart of the movie: how you can love someone and hate them at the same time for reasons that are completely out of your control. It's what makes Brokeback Mountain so much more than the "gay cowboy" movie.