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The death of Heath Ledger on Oscar nomination day set a pall over the 80th annual Academy Awards, already suffering from uncertainty due to the Hollywood writers’ strike.

It was just two years ago that the then 26-year-old actor was nominated for starring in the youth-to-middle-age story of conflicted gay cowboy Ennis Del Mar in Brokeback Mountain. Ang Lee’s groundbreaking film won 76 awards and another 64 nominations around the world including Oscars for director Lee, its screenplay and musical score, but failed to win the Oscar for Best Picture in one of the most stunning upsets in Oscar history.

The film’s Oscar setback was widely attributed to the homophobia of Hollywood’s old guard including actors Tony Curtis and Ernest Borgnine who proudly refused to even watch the film though they had received free DVD screeners in the mail. At the other end of the spectrum, actress-turned-cloistered nun, Mother Dolores Hart, proudly proclaimed that it was her duty as a member of the Academy to watch every nominated film.

Ledger himself won numerous awards for his towering performance including the prestigious New York Film Critics Circle Award, but lost many more including the Oscar to Philip Seymour Hoffman as Truman Capote in Capote, the first of two films about the author’s anguished research into the writing of In Cold Blood. The competing film, Infamous, which was released the following year won no major awards.

Ledger’s loss could hardly be blamed on homophobia as Hoffman’s character was also gay. It was more likely due to the age-old Hollywood truism that young actors like Ledger have their whole lives ahead of them while older, more experienced actors like Hoffman had already earned their dues.

His experience with journalists during the long publicity tour for Brokeback left him drained and suspicious of many in the profession who just wanted to make jokes about the character he had poured his heart and soul into.

Ledger’s astounding performance now has an ironic undertone to it. His most compelling scenes are the ones near the end of the film when his character is at an age that the actor himself will never attain. It brings back memories of James Dean, another actor gone too soon, who played the life story of a character much older than he would ever be at the end of Giant.

His brief, but amazing career can be followed on DVD.

The film which made him a star was 1999’s 10 Things I Hate About You,highlighted by his singing of “Can’t Take My Eyes Off of You” to Julia Stiles. The updated version of Shakespeare’s The Taming of the Shrew, which was also the basis for Kiss Me, Kate, was one of the best teen movies of the last ten years. The two leads are ably supported by Joseph Gordon-Levitt, Larisa Oleynik, David Krumholz, Andrew Keegen, Allison Janney and others. It was directed by Gil Junger.

After the success of that film Ledger could have had a nice career continuing to make teen comedies, but the actor preferred to starve rather than be boxed into that particular corner.

His next major film was 2000’s The Patriot in which he played Mel Gibson’s son. The film directed by Roland Emmerich was one of the better films about the American Revolution of 1776. The superb cast also included Joley Richardson, Jason Isaacs, Chris Cooper, Tcheky Karyo, Rene Auberjonois and Tom Wilkinson.

Ledger, in order to fulfill his deal with Columbia who produced The Patriot, was contractually bound to make 2001’s AA Knight’s Tale, directed by Brian Helgeland, an anachronistic comedy about a 14th Century knight in which rock music plays in the background. Ledger’s charm and that of featured player Paul Bettany make it a pleasant time killer.

Later that year he played a small, but pivotal role in Marc Foster’s Monster’s Ball opposite Billy Bob Thornton and Halle Berry in her Oscar-winning role.

Ledger’s next starring role was in 2002’s The Four Feathers, Shekhar Kapur’s aesthetically beautiful, but long, long version of A.E.W. Mason’s oft-filmed classic tale of cowardice and retribution. He leads a competent cast that also includes Wes Bentley, Djimon Hounsou, Kate Hudson and Michael Sheen.

After a couple of misfires, he came back strong in 2005. First as the alcoholic owner of a surf board shop in Lords of Dogtown. With false teeth and wig he was pretty much playing a character part in Catherine Hardwicke’s film which starred Emile Hirsch. The real life Z-boys portrayed in the film are shown to better advantage in the documentary Dogtown and Z-Boys, but the film does show Ledger’s versatility as an actor.

Later in 2005 he showed up as half of The Brothers Grimm in Terry Gilliam’s dark vision of the life of the fairy-tale storytellers. Matt Damon was the other brother. While the film does not live up to expectations, the performances of the two stars are faultless.

Ledger fared much better with his two year-end films of 2005.

In Lasse Hallstrom’s deft farce, Casanova, he displays expert comic timing and more than holds his own against a supporting cast of expert scene stealers including Jeremy Irons and Oliver Platt. Sienna Miler also makes a fine leading lady.

Best of all, though, was his performance in Brokeback Mountain. Portraying a tightly wound man with bottled up emotions, Ledger provides a textbook study of loneliness and regret. Jake Gyllenhaal and Michelle Williams are terrific as well, but it is Ledger’s character and his performance that haunts you long after the film ends.

Ledger’s last completed film is The Dark Knight in which he plays The Joker to Christian Bale’s Batman. His untimely death has added to the aura of the film that was already being touted as one of the must-see films of the year.

A week ago, if you asked people on the street to name the five most important young actors working today, I doubt Heath Ledger’s name would have come up very often. Now that he is gone people are realizing the magnitude of the loss. His close connection to this year’s Oscar nominees underscores how relevant and connected he was to today’s top talent. You can play the game Six Degrees of Separation between Heath Ledger and all of the acting nominees in this year’s Oscar race. In fact, you need no more than two connections to get to any one of them.

He has direct links to double nominee, Cate Blanchett, his co-star in I’m Not There. She’s nominated for that film as well as Elizabeth: The Golden Age. He also has a direct link to Tom Wilkinson, one of his co-stars in The Patriot. Wilkinson is nominated for Michael Clayton.

Through Wilkinson he’s connected to George Clooney and Tilda Swinton, also nominated for that film. Wilkinson in turn is connected to Tommy Lee Jones, nominated for In the Valley of Elah trough Sissy Spacek, his co-star in In the Bedroom. Spacek won an Oscar opposite Jones in Coal Miner’s Daughter.

Ledger is connected to Into the Wild‘s Hal Holbrook through Emile Hirsch, his co-star in Lords of Dogtown and to Juno‘s Ellen Page through Allison Janney, one of his co-stars in 10 Things I Hate About You.

Matt Damon, Ledger’s co-star in The Brothers Grimm, has a direct connection to Casey Affleck, nominated for The Assassination of Jesse James by the Coward Robert Ford through Affleck’s featured role in Damon’s Good Will Hunting, which won screenplay Oscars for Damon and Affleck’s brother, Ben. The Afflecks in turn are connected to Gone Baby Gone nominee Amy Ryan, Casey’s co-star in that film directed by Ben. Damon is also connected to Charlie Wilson’s War nominee Philip Seymour Hoffman, who played a featured role in the Damon starrer, The Talented Mr. Ripley.

Ledger is connected to Johnny Depp, nominated for Sweeney Todd, through Jonathan Pryce, his co-star in The Brothers Grimm, who was in The Pirates of the Caribbean: At World’s End with Depp. Depp, in turn, is connected to Away From Her nominee, Julie Christie, his co-star in Finding Neverland, which was directed by Marc Forster who had previously directed Ledger in Monster’s Ball.

Chris Cooper, who along with Wilkinson, co-starred in The Patriot with Ledger, provides a connection to The Savages nominee Laura Linney, who played his wife earlier this year in The Breach.

Ledger’s connection to Eastern Promises nominee Viggo Mortensen is through Ned Kelly co-star Naomi Watts who stars opposite Mortensen in the film for which he is nominated. Watts also provides a connection to There Will Be Blood nominee Daniel Day-Lewis who won his first Oscar along with co-star Brenda Fricker in My Left Foot. Watts played a supporting role in Fricker’s Brides of Christ, also featuring Russell Crowe.

Crowe provides the links to La Vie en Rose nominee Marion Cotillard through last year’s A Good Year and American Gangster‘s Ruby Dee with whom he co-starred in that film.

Finally, Brokeback Mountainprovides the connection to two of this year’s nominees, No Country for Old Men‘s Javier Bardem and Atonement‘s Saoirse Ronan. Brokeback‘s Randy Quaid co-starred with Bardem in Goya’s Ghosts, while Brokeback‘s Anne Hathaway co-starred with James McAvoy, Ronan’s Atonement co-star, in Becoming Jane.

Ledger’s career may have been short, but like James Dean, whose career was even shorter, he will be remembered and his films cherished for decades to come.

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