Starting at the top by Egantx7

Question 3

While Mystic Pizza was considered Julia Robert's breakout role, the young man sitting across from her in one dinner scene, her rich boyfriend's younger brother, was played by this young man in his feature film debut ... about a year before he and one of his friends showed up as extras in the Fenway Park crowd while Ray and Terence have a deep discussion in Field of Dreams. Name this five-time Oscar nominee (across three different categories) who has appeared in six films which were Oscar nominated for Best Picture, and has starred in quite a few films with George Clooney.

Matt Damon