Aaron Sorkin Creator, Executive Producer Jeff Daniels Will McAvoy Actor Emily Mortimer Mackenzie McHale Actor John Gallagher Jr. Jim Harper Actor Alison Pill Margaret Jordan Actor Thomas Sadoski Don Keefer Actor Olivia Munn Sloan Sabbith Actor Dev Patel Neal Sampat Actor Sam Waterston Charlie Skinner Actor Marcia Gay Harden Rebecca Halliday Guest Star B.J. Novak Lucas Pruit Guest Star Kevin Rankin Cellmate Guest Star Sarah Sutherland Mary Guest Star Brian Howe Barry Lassenthal Guest Star Chris Chalk Gary Cooper Guest Star Adina Porter Kendra James Guest Star Jon Bass Bree Dorrit Guest Star Margaret Judson Tess Westin Guest Star Wynn Everett Tamara Hart Guest Star Thomas Matthews Martin Stallworth Guest Star John F. Carpenter Herb Wilson Guest Star Trieu Tran Jory Phan Guest Star Riley Voelkel Jenna Johnson Guest Star John Hawkinson Rudy Guest Star Anna Trebunskaya Ticket Agent Guest Star Ilana Guralnik Honeymoon Woman Guest Star Michael Ark Honeymoon Man Guest Star Terence Leclere Photographer Guest Star Francisco Javier Gomez Man on Plane Guest Star Margarita Kallas Flight Attendant Guest Star Nelson Cheng Rebecca's Assistant Guest Star James Holloway Guard Guest Star Frank Cermak Jr. ACN Digital Staffer Guest Star Sarah Scott Davis Terry Smith Guest Star Alan Poul Executive Producer Scott Rudin Executive Producer