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George Clooney and Jake Gyllenhaal chatted before the show in 2006. That year, they were both nominated for best supporting actor, and George walked away with the Oscar for his work in Syriana.

Image Source: Getty
Read More George ClooneyJake GyllenhaalAngelina JolieBen AffleckBrad PittMatt DamonOscarsRed CarpetAward SeasonJennifer LawrenceLupita Nyong'o