The hit-making Broadway writing team of Julia Houston (Debra Messing) and Tom Levitt (Christian Borle) unites with producer Eileen Rand (Anjelica Huston) to create a new musical based on the life of Marilyn Monroe, and seasoned chorus girl Ivy Lynn (Megan Hilty) vies with newcomer Karen Cartwright (Katharine McPhee) for the dream role. Jack Davenport, Raza Jaffrey, Brian d’Arcy James and Jaime Cepero also star.

Ivy (Megan Hilty) and Karen (Katharine McPhee) jump through hoops for the brilliant but temperamental director Derek Wills (Jack Davenport) as they pursue the role of a lifetime. Meanwhile, Julia (Debra Messing) and her husband Frank (Brian d’Arcy James), are frustrated by the red tape of an international adoption process, and Eileen (Anjelica Huston) fights to finance her new musical in the midst of an acrimonious divorce. Christian Borle, Raza Jaffrey, and Jaime Cepero also star.

The search begins for a Joe DiMaggio to play opposite Marilyn - but everyone's first choice, Michael, has a secret. Karen returns to Iowa for a baby shower and must decide what she wants for her future. Eileen begins rounding up investors - but ex-husband Jerry may already have poisoned the well.

Karen must learn to advance in the high-stakes world of Broadway, as Derek hosts a party for hot young star Lyle. Eileen tries a sly new strategy for raising funds, while Tom goes on a first date.

Karen finds a new use for her acting talents as she joins Dev at a high-powered government party. The drama between Michael and Julia heats up, as Eileen and Tom's ambitious assistant Ellis forge an alliance. Ivy senses trouble in her relationship with Derek.

Ivy faces major vocal issues, while Julia struggles to avoid Michael. Meanwhile, Karen books a side gig at a bar mitzvah.