2006

George Clooney

March 05

I'd Like to Thank the Academy. . .

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."

George Clooney

November 15

Sexiest Man Alive...Again

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.

2007

George Clooney

September 21

Wild Ride With New Gal

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.

George Clooney

December

Reuniting with Renée – and Oscar

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.

2008

George Clooney

February

Clooney Covers Time

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.

2009

George Clooney

July

An Italian Romance

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.

George Clooney

December 23

'Up' For Oscar

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.

2010

George Clooney

August 29

A Star Humanitarian

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."

2011

George Clooney

June

Split Decision

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.

George Clooney

September

Northern Exposure

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."

Photo Credits

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

Name
George Clooney
Date of Birth
May 06, 1961
Birth Place
Lexington, Ky.
Relationships
Amal Alamuddin, fiancée (2013 to present)
Stacy Keibler, ex-girlfriend (2011 to 2013)
Elisabetta Canalis, ex-girlfriend (2009 to 2011)
Sarah Larson, ex-girlfriend (2007 to 2008)
Krista Allen, ex-girlfriend (on & off since 2002)
Maria Bertrand, ex-girlfriend (2002)
Lisa Snowdon, ex-girlfriend (on & off since 2000)
Celine Balitran, ex-girlfriend (1996 to 1999)
Karen "Duff" Duffy, ex-girlfriend (1995)
Kelly Preston, ex-girlfriend (1987 to 1989)
Talia Balsam, ex-wife (1984; 1989 to 1992)
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Edited by Julia Wang

George Clooney

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