Suggestions by @lindseyolson

Bradley Cooper

as "Bud" Flynn in Lost Lambs

Sadie Sink

as Abigail in Lost Lambs

Maude Apatow

as Norma Smith Conroy in The Dutch House

Rachel McAdams

as Elna Conroy in The Dutch House

Victoria Pedretti

as Andrea Smith Conroy in The Dutch House

Mila Jones

as KitKat in Anna O

Hugh Grant

as Richard Ogilvy in Anna O

Israel Broussard

as Doug in Anna O

Karen Gillan

as Harriet Roberts in Anna O

Emily Blunt

as Clara in Anna O

Jennifer Connelly

as Emily Ogilvy in Anna O

Avantika

as Indira Sharma in Anna O

Odessa A'zion

as Anna Ogilvy in Anna O

Jude Law

as Dr. Benedict Prince in Anna O

Lily Tomlin

as Dr. Virginia Bloom in Anna O

KJ Apa

as Young Chris Davis in Such a Bad Influence

Keanu Reeves

as Young Chris Davis in Such a Bad Influence

Jennifer Aniston

as Erin Davis in Such a Bad Influence

Amanda Seyfried

as Hazel Davis in Such a Bad Influence

Dove Cameron

as Evelyn Davis in Such a Bad Influence