On October 26, 2016, multiple news outlets reported that Amazon had won a bidding war among six entities and committed to a straight-to-series order with a $70 million budget for an eight episode first season.

[9] From August to October 2017, a series of announcements revealed that Isabelle Huppert, Christina Hendricks, John Slattery, Jack Huston, Amanda Peet, Marthe Keller, Aaron Eckhart, Corey Stoll, Andrew Rannells, Mike Doyle, JJ Feild, Janet Montgomery, Paul Reiser, and Diane Lane had been cast in the series.

These actors included Noah Wyle, Hera Hilmar, Kathryn Hahn, Kerry Bishé, Jay R. Ferguson, Ben Miles, Mary Kay Place, Griffin Dunne, Cara Buono, Ron Livingston, Jon Tenney, Clea DuVall, Radha Mitchell, Hugh Skinner, Juan Pablo Castañeda, Emily Rudd, Adele Anderson, Annet Mahendru, Louise Bourgoin, Inès Melab, Michael O'Neill, and David Sutcliffe.

A red carpet arrival was originally scheduled to take place before the screening but was canceled out of respect for the victims of the Woolsey Fire, which was still burning in the Los Angeles and Ventura counties.

The website's critical consensus reads, "Matthew Weiner's return to television is as handsomely made as it is ambitious and sprawling—unfortunately, it's also fatally indulgent, asking for the utmost patience from audiences without a compelling incentive.