Suggestions by @taissaturner

Madelyn Cline

as Judith Todd Neuenhaus in Will Win, Could Win, Should Win

Bailey Bass

as Delilah de Angelis in Will Win, Could Win, Should Win

John Cho

as Owen Han in Will Win, Could Win, Should Win

Phoebe Dynevor

as Kennedy Pendergast in Will Win, Could Win, Should Win

Emily Carey

as Freya Pendergast in Will Win, Could Win, Should Win

Alfonso Gomez-Rejon

as Director in Will Win, Could Win, Should Win

Jamie Babbit

as Director in Will Win, Could Win, Should Win

Marielle Heller

as Director in Will Win, Could Win, Should Win