He won the Academy Award for Best Live Action Short Film for his 1996 short film Dear Diary and an Emmy for Outstanding Directing for a Comedy Series for the pilot episode of Entourage (2004), and has since directed the successful studio films The Devil Wears Prada (2006), Marley & Me (2008), and Hope Springs (2012). His birdwatching comedy, The Big Year, starring Steve Martin, Owen Wilson, JoBeth Williams, and Jack Black, was released in October 2011.