Suggestions by @taissaturner

Alana Haim

as Virginia Brightman in Will Win, Could Win, Should Win

Meghann Fahy

as Marjorie Baxter in Will Win, Could Win, Should Win

Jesse Eisenberg

as Steven Abrams in Will Win, Could Win, Should Win

Kedar Williams-Stirling

as Zackery Beckett in Will Win, Could Win, Should Win

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