OK, this list is now complete and MonStar gets to start the next game.
In addition to those mentioned, you could also list ...
Christopher Plummer - Cold Creek Manor (2003)
Olympia Dukakis - In the Land of Women (2007)
Eddie Redmayne - The Yellow Handkerchief (2008)
Robert De Niro - What Just Happened (2008)
Sean Penn - What Just Happened (2008) - he also wrote the screenplay and directed Into the Wild (2007)
Furthermore, William Hurt also appeared in Into the Wild, and Melissa Leo was also in Welcome to the Rileys (2010).
Finally, even though this film won't get released until November, Mary Steenburgen will appear in Happiest Season (2020) with Kristen.
Oh yeah, these two did not act in films with Kristen, thus they would not have counted, but Ang Lee directed Billy Lynn's Long Halftime Walk (2016) and Woody Allen wrote and directed Cafe Society (2016).
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