Clooney is nominated for three Oscars: Best Supporting Actor for Syriana, and Best Original Screenplay and Best Director for Good Night, and Good Luck. In his acceptance speech for Best Supporting Actor, Clooney admits "we are a little bit out of touch in Hollywood every once in a while. I think it's probably a good thing. We're the ones who talked about AIDS when it was just being whispered, and we talked about civil rights when it wasn't really popular…I'm proud to be a part of this Academy, proud to be part of this community, and proud to be out of touch."
The silver-haired bachelor becomes the second celebrity to be twice-honored as PEOPLE's Sexiest Man Alive. He shares the double-duty with buddy and Ocean's 13 costar Brad Pitt. Months later, he's named one of Time magazine's 100 Most Influential People for "using star power to illuminate the crisis in Darfur." After making his first trip to Darfur in 2006, Clooney made the TV special A Journey to Darfur with his father Nick, and advocated for action in the U.S.
After sporting Sarah Larson on his arm at the Venice and Deauville film festivals, Clooney, 46, and his new squeeze, 28, are involved in a motorcycle accident. The Harley-Davidson they were riding was hit by a car in New Jersey. Clooney suffers a hairline fracture of a rib, while Larson suffers a broken foot. In 2008, Larson becomes the first girlfriend ever to accompany Clooney to the Academy Awards, but by May, they calls it quits.
After starring in the drama Michael Clayton – for which he earns a Best Actor Oscar nomination – Clooney appears on the cover of W with Renée Zellweger. Besides promoting their 2008 romantic comedy Leatherheads (which Clooney also directed), the old friends poke fun at their alleged romantic relationship and their work together.
Days before the Academy Awards – where Clooney is up for Best Actor – he appears on the cover of Time. "For me, it's like being Hillary Clinton," says the Michael Clayton star. "If it weren’t for Barack Obama, it would have been a very good year." Adds Clooney: "I thought Daniel Day-Lewis had the best performance of the year." Clooney's Oscar pick for Best Actor is spot on, as Day-Lewis walks away with the statue.
Clooney, 48, is spotted around Italy with Italian model and actress Elisabetta Canalis, 30. In September, the pair steps out publicly at a screening of his film, The Men Who Stare at Goats, at the Venice Film Festival, and she accompanies Clooney to the 2010 Academy Awards. "It's nice to see my friend so happy," Matt Damon says of his close pal's romance.
Clooney plays a lifelong bachelor – a character that parallels his real life – in Jason Reitman's Up in the Air. "I’m not completely unaware of people’s perceptions of me," he tells EW. "I sort of felt like, if you were ever going to deal with it, this is probably the best way to do it and the best person to do it with." The film earns Clooney and his leading ladies, Vera Farmiga and Anna Kendrick, Oscar nominations.
Clooney, who organized an all-star telethon for the victims of the Haitian earthquake, accepts the Bob Hope Humanitarian Emmy award. "Its important to remember how much good can get done because we live in such strange times where bad behavior sucks up all of the attention and the press," says the actor, who tops the box office with The American in September. "And the people who really need the spotlight: the Haitians, the Sudanese, people in the Gulf Coast, Pakistan – they can't get any."
A few months after celebrating the actor's 50th birthday, Clooney and Canalis end their two-year relationship. "We are not together anymore. It's very difficult and very personal, and we hope everyone can respect our privacy," the exes say in a joint statement.
Clooney, 51, goes public with his budding romance with Stacy Keibler, 31, at the Toronto Film Festival. "They have good chemistry, and she can hold her own with the boys," a source says of the former WWE star. "I'm in heaven," Keibler Tweeted in July, adding, "I am the luckiest girl in the world."
BIOGRAPHY (top to bottom): Steve Granitz/WireImage; Scott Wintrow/Getty; Courtesy of W; Kevin Mazur/WireImage; Courtesy Entertainment Weekly; Paul Buck/Landov; LFI; Macca/Todd G/Splash News Online