The Crazy Ones

The Face of a Winner (Season 1, Episode 12)

TV-PG

TV Episode | 30 min | Comedy

When Simon mixes up the assignments in the office, he puts Sydney on an account for a video game that she becomes addicted to winning.

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Cast	+ Add Cast
11 cast members

Name	Known for
Robin Williams Simon Roberts Simon Roberts See fewer	Mrs. Doubtfire (1993)
Sarah Michelle Gellar Sydney Roberts Sydney Roberts See fewer	Buffy the Vampire Slayer (1997)
James Wolk Zach Cropper Zach Cropper See fewer	Mad Men (2007)
Hamish Linklater Andrew Keanelly Andrew Keanelly See fewer	The Big Short (2015)
Amanda Setton Lauren Slotsky Lauren Slotsky See fewer	Sex and the City (2008)
Lenny Jacobson Jerome Jerome See fewer	Peacemaker (2022)
Steven Boyer Squirrel Squirrel See fewer	Trial & Error (2017)
Thomas Fowler Desmond Desmond See fewer	Chalk It Up (2016)
Zylan Brooks Zen-Phoria Exec (as S. Zylan Brooks) Zen-Phoria Exec (as S. Zylan Brooks) See fewer	Matlock (2024)
Rachel Rodier Young Sydney Young Sydney See fewer	Major Crimes (2012)
Fatima Grate Rosa (uncredited) Rosa (uncredited) See fewer	Genius in Heels (2009)