Following his growing success he decided to try his luck
in America where he soon appeared in the “Roar”- Fox's new warrior drama –
costarring Keri Russel.

 A
leading role in the 1999’s “10 Things I Hate About You” resulted in a deluge of
offers to appear in similar teen-film roles, but Heath accepted none of them.
"I had a year where I sat around on my butt and declined generous offers
to do more teen movies and more of the same characters as the one from “10
Things”,” he says. “I was literally living off instant noodles and water just
because I was sticking to my guns. It was very hard because they offered you a
lot of money”.

 Trying to show “the other side of his talent” he
accepted a role in a very serious war drama “The
Patriot” (2000). Nominated for 3 Oscars.
Achived 8 wins
&
17 nominations, with Heath Ledger's winning in Favourite Male Award by Blockbuster Entertainment in 2001

 After that he had numerous roles in very big movies,
such as “A Knight's Tale” (2001). Tagline "He didn't make the rules. He was born to break them."

After "A Knight's Tale" Heath accepted a role in "Monster's Ball" in 2001. There he had a very small third plan role as a prison guard Sonny Grotoski.Tagline "A lifetime of change can happen in a single moment."

Set in 1884 Sudan, this fifth film to be adapted from the A.E.W. Mason
novel follows a British officer who resigns his post right before his
regiment ships out to battle the rebels. Perceiving his resignation as
cowardice, his friends and fiancée give him four white feathers, the
symbol of cowardice, but little do they know he's actually going
undercover and plans to redeem his honor. Heath plays the main caracter Harry Faversham.

Next year, after 'The Four Feathers', Heath accepts the role in 'Ned Kelly' where he also plays the main caracter. The movie achived 3 wins and was nominated for
13 times. The major of them where presented by Australian Film Intitute.

In 2003 Heath plays Alex Bernier in "The Order". Alex Bernier (Ledger) is a member of an arcane order of priests known
as Carolingians. When the head of the order dies, Alex is sent to Rome
to investigate mysterious circumstances surrounding the death. The body
bears strange marks on the chest which may or may not be the sign of a
Sin Eater (Furmann), a renegade who offers absolution, last rites and
therefore a path to heaven outside the jurisdiction of the church. Alex
enlists the aid of his old comrade Father Thomas (Addy) and of a
troubled artist (Sossamon) upon whom he once performed an exorcism. He
soon finds himself plunged into a mystery only to find himself at the
heart of it.

A fictionalized take on the group of brilliant young skateboarders
raised in the mean streets of Dogtown in Santa Monica, California. The
Z-Boys, as they come to be known, perfect their craft in the empty
swimming pools of unsuspecting suburban homeowners, pioneering a
thrilling new sport and eventually moving into legend. Heath plays Skip.

The action-adventure tale revolving around the legendary German
brothers Jacob and Wilhelm Grimm - the fictional plot has the folklore
collectors, now called Jake and Will, traveling from village to village
pretending to protect townsfolk from enchanted creatures and pulling
off exorcisms. They are put to the test when they encounter a real
magical curse, requiring genuine courage.

Also in 2005 Ledger plays Ennis Del Mar in Brokeback Mountain. Set against the sweeping vistas of Alberta's Rocky Mountains, this film
tells the story of two young men - a ranch-hand and a rodeo cowboy -
who meet in the summer of 1963 and unexpectedly forge a lifelong
connection, one whose complications, joys and tragedies provide a
testament to the endurance and power of love. The movie won 3 Oscars and another 78 wins
&
64 nominationsQuote "The challenge was to capture the stillness of him. I have kind of
semi-frantic, nervous energy. Harnassing that was something I thought
I`d have to work out. Shooting in the wilderness, the stillness became
like this innate quality." -on his character "Ennis" in Brokeback
Mountain (2005).

Heath Ledger plays the fabled romantic as a man who, after failing to
win the affection of a particular Venetian woman, strives to discover
the real meaning of love. Casanova falls in love with Francesca, who thinks he is a friend of himself
even though he is engaged Victoria, who is the love of Giovanni,
Francessca's brother. Francessca is betrothed to Paprizzio who thinks
Casanova is the feminist writer Guardi, who is really Francessca's
nomme de plume. Amidst all these secret identities and
misunderstandings, the Catholic Church sends Pucci to bring Casanova
and Guardi to trial for heresy.