Julia Roberts as Anne Tuohy (The Blind Side, 2009)
Even worse than turning down a role that goes on to be legendary and iconic: When that role goes on to win an Academy Award as well. This was unfortunately the case for Julia Roberts in 2009, when she turned down the lead role of Anne Tuohy in The Blind Side. The part eventually went to Sandra Bullock, who received an Oscar for Best Actress for the role. That same year, Roberts appeared in Duplicity, which received mixed reviews and only got Roberts a Golden Globe nomination for Best Actress.