Brad Pitt, Angelina Jolie, and Jennifer Aniston in the Same Room at the 2009 Academy Awards
In 2005, the world was surprised when Brad Pitt and Jennifer Aniston ended their marriage. Perhaps Pitt’s “Mr. & Mrs. Smith” co-star, Angelina Jolie, wasn’t as shocked. Four years later, at the Oscars, things were still awkward between Pitt and Aniston. Pitt and Jolie sat in the front row while Aniston presented an award. As Aniston walked off stage, Pitt and Jolie smiled and clapped. Aniston joined her date, John Mayer, creating a unique moment at the event.