Michael Cristofer plays Jerry, Eileen's soon-to-be-divorced husband and former producer partner. A recurring humorous scene in the play is Eileen throwing a drink in Jerry's face. Will Chase plays Michael Swift, a star in the musical theater industry who once had an extramarital affair with Julia and now plays the role of Joe DiMaggio in the Monroe musical. Wesley Taylor as Bobby, one of the vocalists who has the courage to express his opinions. Grace Gummer as Eileen and Jerry's daughter. Savannah Wise as Jessica, a dancer who is friends with Karen. Phillip Spaeth as Dennis, Ivy's friend and dancer, who had a relationship with Tom. Uma Thurman plays Rebecca Duvall, a big-time movie star who wants to star in the Monroe musical and will have a five-episode arc. Thorsten Kaye as Nick, the bartender who flirts with Eileen. Joshua Bergasse as Josh, Monroe's assistant choreographer for the musical. Emory Cohen as Leo Houston, Julia and Frank's son. Maddie Corman as Rene Walters, an adoption agency worker who is helping the Houston family adopt a Chinese child. Finnerty Steeves as Moira, a staff member on the Monroe musical. Becky Ann Baker as Karen's mother. In reality, she is the wife of actor Dylan Baker, who plays Karen's father. Dylan Baker as Roger Cartwright, Karen's father. Jennifer Ikeda plays Lianne, a waitress at the restaurant where Karen works. Eisa Davis as Abigial, Eileen's divorce lawyer.