This was a real tough one, as is often the case crossing a generation. In the end a family link proved the key for a four move solution!
1. Julie Andrews to Anne Hathaway in The Princess Diaries; 2. Hathaway to Jake Gyllenhaal in Brokeback Mountain; 3. Jake to sister Maggie in Donnie Darko; and 4. Maggie was in Confessions of a Dangerous Mind with Sam Rockwell.