Aaron Ashmore played "Student in Pageant" along with his twin brother Shawn Ashmore in Married to It (1991). Shawn was also in The Ruins (2008) with Jena Malone, who was in Donnie Darko (2001) with Jake. Jake :: BBM.
I haven't played in ages, and not sure who has been done yet. Sorry if this is a repeat (although to me that's okay, because there can be more than one way to get there):
Next: Justin Kirk