When Ivy brings Sam back to town, Tom finds himself in an awkward situation. Jimmy and Derek clash over their vision for "Hit List," while both Ana and Karen struggle to stand up for what they want.

After Leigh Conroy joins the cast of "Bombshell," Tom finds himself struggling to diffuse the years of tension between her and Ivy. Jimmy and Karen's connection is threatened by both Ana's newfound success and an unexpected visitor. Derek learns more about Jimmy's past just as the public sees their first piece of "Hit List."

With Liza Minnelli in town, Tom plans a surprise for Ivy in an attempt to find a balance between their work life and their friendship. Relations between Karen, Jimmy, and Derek explode just as Hit List's rehearsal process nears its close. While Richard asks Eileen to spend less time at work and more time with him, Julia finds herself also pulled away from Bombshell by an unlikely source.

As Tom and Julia race to ready "Bombshell" for previews, Tom's eagerness to prove himself may not be the best thing for the show. An on-stage mishap forces Ivy to make an important decision, while tension rises at "Hit List" as Karen becomes suspicious of Derek's motives towards her.