The project was originally developed as a collaboration between Brad Pitt and Adam Sandler. Pitt exited shortly before production, and George Clooney was cast in the role.
George Clooney joined the project within a day of reading the screenplay. He later joked that his only concern was adapting to Noah Baumbach's tendency to shoot numerous takes, which contrasts with his own preferred working style.
Several of the projected film clips in the final scene come from George Clooney's real filmography, including Syriana (2005), Michael Clayton (2007), The Peacemaker (1997), In amore niente regole (2008), Tra le nuvole (2009), The American (2010), La sottile linea rossa (1998), and Burn After Reading - A prova di spia (2008).
George Clooney has noted that, unlike his character in the film, he has a close and loving relationship with his father, journalist Nick Clooney.
Jim Broadbent's character was inspired by the late director Peter Bogdanovich, a close mentor and father-figure to writer-director Noah Baumbach. Like Bogdanovich, the character experiences financial decline and is known for his trademark neckerchief.