Back from a successful run in Boston, Eileen, Julia and Tom are blindsided by both personal and professional obstacles as they seek to take "Bombshell" to Broadway. Karen consults her new mentor, Broadway star Veronica "Ronnie" Moore, as she finds herself on the brink of fame, but her success may come at cost to Ivy. A new talent is discovered in an unexpected place. Meanwhile, Derek copes with a damaging accusation.
The second season begins with "Bombshell" running into financial trouble that threatens the production. Meanwhile, Karen is mentored by a Broadway star and discovers a new artist in an unexpected place; and Julia faces a personal crisis with her husband.
Partnerships are tested as Eileen asks Tom and Julia to contend with an unwelcome new collaborator, while Jimmy and Kyle prepare to present their work for the first time. Derek attempts to get Ronnie back on his side. Ivy finds it hard to move on, but help from an old friend might take her one step closer to her dream.
Derek calls in help for a special event, but Jimmy's pride might get in the way of a huge opportunity Karen orchestrates for him and Kyle. Peter challenges Julia's pride as they continue to work together. Meanwhile, Ronnie struggles to assert her independence from a powerful mother, as Eileen finds herself at a moral crossroads with huge ramifications for "Bombshell".
Julia's fears increase when Tom airs his suspicions of Peter. Jimmy and Kyle confront their own crisis of confidence as "Hit List" is read for the first time. Meanwhile, Ivy realizes her triumph might not be all she hoped when she meets her new co-star, Terry Falls, and Karen wonders if she can trust Jimmy.
Derek and Karen find themselves at a surprising crossroads, forcing one of them to make a difficult choice. Jerry's uneasy partnership with Eileen hits a snag, as does "Hit List's" first performance at the Fringe Festival. Meanwhile, Ivy's last-ditch effort to save her and Terry's show has unexpected results.
New circumstances give rise to conflicts as Karen, Tom, Julia and Derek adjust to their new surroundings. Tensions at "Liaisons" are also coming to a boil, ensuring that the show will find its place in Broadway history. Meanwhile, Eileen may have found the key to saving "Bombshell" with the help of her daughter, Katie.
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".
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 onstage mishap forces Ivy to make a choice, while tension mounts at "Hit List" as Karen becomes suspicious of Derek's motives towards her.
It's 'Bombshell's' opening night. As Ivy's nerves get the better of her, support comes from an unlikely source. Meanwhile, Tom and Julia look to their next project. 'Bombshell's' success may be in jeopardy as Eileen's issues with Richard come to a head. Jimmy finally opens up to Karen about his past, but is it too little too late?
An off-the-rails Jimmy threatens "Hit List's" future, as Karen, Derek, Ana and Kyle try to help him before something bad happens. Tom and Julia's partnership is strained to the breaking point just as Ivy, Eileen, and the entire "Bombshell" team are running themselves ragged to outshine the competition.
An unexpected event bonds both 'Bombshell' and 'Hit List'.
With his sights set on the Tony, Tom pulls out all the stops at a Houston & Levitt tribute night, but can Julia turn away from 'Hit List' long enough to help? Ivy is afraid of damaging her reputation when Tom asks her to perform a risquÃ© number. The cast of 'Hit List' is rocked by a betrayal close to home.
It's a crucial moment for both shows as Tony nominations loom, but keeping your eye on the prize can be hard. As Tom crosses an influential Tony voter and Ivy copes with some very distracting news, Derek's past has repercussions for the entire "Hit List" team.
On Tony night, the awards might not provide the answers everyone is looking for. As Jimmy faces a final reckoning, Tom, Julia, Derek, Karen, Ivy, and most of all, Eileen wait to see if the ceremony will confirm their place in the Broadway pantheon once and for all.