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- With their latest show "Heaven on Earth" still running on Broadway, the song and book writing team of Julia Houston and Tom Levitt have decided to take a professional break, in part to give Julia and her husband Frank time to go through an adoption process and in turn allow Julia to be a stay-at-home mom. But a germ of an idea from Tom's new assistant Ellis Tancharoen leads to the thought of writing a new musical based on Marilyn Monroe. A further move by Ellis which could kibosh the idea before it even gets off the ground instead generates buzz around the new project. On board is producer Eileen Rand, who, because of divorce proceedings, is unable to continue work on what would have been her focus of a revival of "My Fair Lady". Eileen wants to hire Derek Wills to direct, much against Tom's wishes as the two hate each other. Julia and Tom believe that their friend Ivy Lynn, who currently performs in the ensemble of "Heaven on Earth", would be perfect to play Marilyn. But during open auditions, an unknown named Karen Cartwright makes an impression on Derek, enough so that she is called back. Beyond her unknown status, other things working against Karen are her New York-phobic Midwestern parents who don't agree with her choice of career, and Karen's own morals which could stop her from doing what she believes she needs to do to get the part.
- Ivy and Karen learn that they are the final two auditionees standing for the role of Marilyn. After an excruciating four day delay, they learn that they are being called back for yet another audition instead of hearing the definitive news of if they got the part. In the lead up to that audition, Dennis, a dancer friend of Ivy's, acts as her unofficial spy in the enemy camp. And Karen makes a decision about her rehearsals that could jeopardize her relationship to Dev. Behind the scenes, Derek still believes Karen is the better candidate, as her freshness and inexperience will add the needed dimension into the role, while Tom is Ivy's biggest backer, believing she has the experience and vulnerability in her personality to carry off the part successfully. Julia is somewhat caught in the middle, she who wants to seem impartial. A personal move by one could sway the vote. Meanwhile, Julia and Frank receive some news about their adoption process which makes Frank reconsider, much to Julia and Leo's dismay. And Derek receives some news about Eileen's divorce proceedings which may jeopardize the work thus far on the Marilyn project.
- With Ivy cast as Marilyn and Karen cast in the ensemble, the production moves into the workshop phase, the $200/week paycheck per person which causes some unspoken issues among many of the cast. For Karen, a trip back to Iowa for a friend's baby shower places her life into perspective for her, her friends and her family. Ivy's own insecurities surface as she wonders if she only got the part because she is sleeping with Derek. With the principal female lead cast, the casting moves to the three male leads, the first being Joe DiMaggio. The name that comes to mind for most is Michael Swift, which causes Julia some unspoken anxiety. She eventually admits the reason for her anxiety to Tom, which could add an extra dimension to her already tenuous relationship with Ellis. And Eileen continues to have problems attracting investors, as many of her past investors had always dealt with Jerry, who they trust more than her.
- In the workshop, Derek seems to be changing both his professional and personal allegiance from Ivy to Karen, which places both women in an awkward and embarrassing situation. While Ivy continues to take her frustration out on Karen, Karen seeks support from Dev, who provides little as he is focused on his own issue of a job promotion. Despite Karen feeling that one of Dev's professional associates has her sights on him, Karen is able to funnel her energies and channel a little bit of Marilyn in helping Dev in his cause. Meanwhile, Leo gets into a situation with the police, which is bad timing for Julia as Frank is out of town, she has to complete the book, and her mind is focused on trying to avoid Michael (without success), with who the sexual tension continues. Tom indirectly comes to Leo's rescue, which factors into Tom's continuing question of whether he likes John as a potential boyfriend or not.
- The workshop is being shown to potential investors. It's not good timing for either the creative team or Ivy has she has come down with a vocal stress issue, which is affecting her ability to sing. Ivy is prescribed steroids to overcome the issue, but since she is hypersensitive to drugs, she has to make the decision to let the stress heal itself without the drugs which means probably allowing Karen to take over the lead for the workshop and potentially for the show, or to take the steroids and face the side effects. Meanwhile, Karen reluctantly accepts a gig that was originally Ivy's to sing at a bar mitzvah. Performing at the gig has an unexpected result for Karen. Eileen is feeling more confident in her life with Ellis now acting as her assistant. Tom continues his courtship with John. And after her passionate kiss with Michael, Julia tries whatever she can to avoid any personal contact with him, with little success.
- 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.
- In the lead up to showing the workshop to potential investors, things don't seem to be going well for anyone involved with the show except Karen, whose biggest issue is if her allegiances lie with the show or furthering her music career, as a big time music producer, who only has a limited time to see her, can only do so during the investor's show. Eileen is having problems with the building manager and getting the boiler repaired in time for the show as the building is like a furnace. Eileen gets some help on this matter from an unexpected source, which may add a little spice to her personal life. Julia's work is suffering because of her angst over her continuing sexual relationship with Michael, and the fact that she learns that Leo knows about the affair. And Ivy, still recuperating from her vocal strain, has the additional concern about her visiting hypercritical mother, ex-Broadway star Leigh Conroy, who, in Ivy's words, sucks all the spotlight on herself like a black hole whenever she's around. Ivy is thrown for a further loop when two specific people show up for the show, one who could affect her performance and another who could jeopardize her maintaining the role of Marilyn regardless of her performance. After the show, the creative team have to make some tough decisions, some which are made more from a personal rather than professional stance.
- It's been two days since the workshop was presented to potential investors. Since, Derek and Eileen have gone into relative hiding, not responding to any left messages. Is silence a good thing for those involved in the show? There is one person who does know his fate regarding the show. One other person has heard from the producing/directing team. Derek asks Karen to prepare and present some new music without telling anyone, but most specifically Tom and Julia, about what she's doing until it is presented. Karen is concerned about the secrecy revolving around this request. She is still equally as concerned about Dev's relationship with R.J., which grows if only because of his on-going battle for the press secretary job. Back with the show, Ellis, does whatever he can to find out what's going on. What he sees he is more than willing to divulge to those who he feels should know, but what he sees also influences what he wants to do to further his career. Although she does care that she has yet to hear back from Eileen, Julia is still preoccupied with thoughts of Michael and how to handle that situation, and Leo's impending court date regarding his marijuana possession. And Eileen's saintly daughter, Katie, comes home for a visit. Her visit is not by accident. Katie tries to add some semblance of civility to her parent's crumbling marriage, as well as some sense of what is right and wrong into Eileen's current professional life.
- With Derek and Eileen's experiment to take the show in a different direction musically a failure, everything about the show truly is up in the air. With much work ahead of them before anything substantive can be shown, Derek isn't sure he can wait and thinks about quitting. Eileen has her own idea of directors to replace him. The one thing that they can agree on is that a star is needed to headline the show. Ellis believes that his behind-the-scenes work in getting that star will provide him with the ammunition he needs to get his career to that next level. Despite the tremendous amount of work they have to do on the show, both Julia and Tom become further preoccupied with their respective personal lives. Frank believes the song he finds on Julia's nightstand is an indication that not all is all right in the Houston home life. Frank decides to take direct action at least to receive his small sense of justice. And Tom receives yet another piece of information about John which is the latest in a long string of potential deal breakers in their relationship. He also has to deal with a despondent Ivy, who believes she is handed one bad piece of news after another. The latest is losing a part to Karen - this one for a national commercial - which in part leads to an on-stage incident at "Heaven on Earth". That incident leads to an unexpected albeit temporary point of connection with Karen.
- The Marilyn project has a new title and a new star: "Bombshell" with movie star Rebecca Duvall in the lead role. The production still has short term problems in that Rebecca is stranded in Cuba and potential investors won't provide the money until they see some of the finished work. As such, Derek names Karen the understudy, she who is to work on the role to show the investors the project's progress in Rebecca's unavoidable absence. Ivy, who is angry that she wasn't given the understudy position but understanding of the reason why, tries a different tact to get back into the good graces of anyone of any importance who will listen. Karen being the understudy also doesn't please Dev, who learns of Karen's history with Derek and who is facing his own career crisis. Karen herself may regret taking the role based on her treatment by Derek. On the investment front, Nick believes he has a potential investor for the show. Ellis warns Eileen that having Nick as an investor has its risks. Meanwhile, Julia has told no one of her and Frank's marital problems. It causes a potential issue with an interview, and a real issue in Tom and Julia's professional partnership anniversary ritual, this one being their tenth. And although Tom has a long list of potential deal breakers in his relationship with John, John may have an important one of his own.
- Rebecca Duvall has finally made it to rehearsals. Many in the company are in awe of working on a project with such a big star. But Rebecca turns out to be less than the perfect leading lady for this project: she isn't a strong singer, and her many demands include having more book and less song in the production. The creative team have to decide how to deal with Rebecca, which may work to Ivy's benefit. Ivy is hoping that Rebecca crashes and burns so that she can work her way back into the lead role. This situation brings her together with Karen in an interesting meeting point. Meanwhile, some relationships are flourishing while others are floundering. Karen and Dev seem to be drifting apart as Dev deals with not getting the press secretary job, which he has yet to tell Karen. He seems to feel more comfortable talking to R.J. about his problems. With a little help from Julia, Tom and Sam embark on the start of their relationship. It ends up being a little different than what Tom had expected, but it gives him some time for self-reflection on why he has never been in a long term relationship. Julia and Frank have to work together to deal with former A-student Leo, who is now failing in a few subjects. Julia and Frank have different approaches in dealing with the issue. Eileen decides to confront at least the issue of Nick in moving forward personally and professionally. And Ellis, in a so-called personal relationship solely to advance his career, makes a misstep which takes him one step backward.
- As Rebecca immerses herself further into the project, she demands change after change to turn it more into a play and less as a musical to work toward her own strengths, or more precisely to steer away from her weakness as a singer. Rebecca also befriends Karen, who, to the media, becomes Rebecca's new BFF to the point of speculation that they are lovers. Regardless, Karen welcomes her new friend, being able to bask in the media limelight for whatever reason and enjoy the trappings associated with being with a movie star. However, the "forever" part of BFF might not fit into Rebecca's grand plan. Unknown to Rebecca, there are others behind the scenes that are maneuvering for Ivy to emerge the star despite Derek's seeming obsession with Karen in the role. Rebecca and Karen's friendship also has an effect on Karen and Dev's relationship. Meanwhile, Eileen gets a head's up from Ellis that Jerry will be attending the same social function as her. Rather than it be an awkward situation, she believes she can take advantage of it by bringing Nick to the event with her to show Jerry that she has moved on with her life. And Julia and Frank go into a panic when they discover that Leo has run away. Julia believes that Mason, who feigns not knowing where Leo is, is not telling the whole truth.
- The production has moved into the tech phase, with the first show in two days in Boston. Derek is already stressed with all he has to do to get the show ready, which is not helped by their leading man giving immediate notice since he got another job. The easiest thing to do would be to bring Michael Swift back. Although Julia is at home with Frank trying to repair their marriage, Michael back in the show may throw a wrench into those repairs. Julia and Eileen have a standoff on the issue, Julia who threatens to quit if Michael returns, while Eileen still figures that bringing Michael back is the path of least resistance unless Julia does make good on her promise. Derek and Rebecca seem to have a new professional understanding, which Ivy takes to mean that they are embarking on a personal relationship. Beyond the emotional loss if Derek is indeed carrying on with Rebecca, Ivy has to brace herself for whatever professional strategic loss that means specifically for this show. Meanwhile, Dev is feeling at a professional loss himself, the emotions with which he tries to transfer to his personal life. This transfer in turn affects Karen, who can't think of anything else but the tech at the present time. And since they are in Boston which is Sam's home town, Tom wants to meet his family.
- In the lead up to tonight's first preview of three in a row in Boston, many things going on behind the scenes are preoccupying the minds of the cast and creative team. Julia has returned from her hiatus, but is not talking to Tom, who she believes should have stuck up for her in demanding that Michael not return to the show. Frank and Leo accompany her for support, and to ensure that Michael, who Julia avoids at all cost, does not move in on Julia himself. While Derek told Ivy only three days earlier that he loves her and she now learns that he is sleeping with Rebecca, Ivy looks to another man for emotional support through sex, that man being Dev. Karen is in emotional limbo herself after telling Dev that she can't marry him right now, and in turn he not returning her several messages. But the first preview does happen, and like most previews, the entire team has some work to do following. One major incident happens at the end of the preview which causes Eileen to fume, leads to Tom and Julia, who still aren't talking to each other, needing to rewrite the ending, and causes Rebecca to have a crisis of faith in herself. Over the next day as many of the pre-preview issues try to work themselves out, some rogue peanuts and a little bit of religion thrown in courtesy of Sam's family's church may add a little perspective to the proceedings.
- Now that Rebecca has decided not to return to "Bombshell", the creative team, beyond the need for Tom and Julia to rewrite the ending which will include one more song, has a major decision: whether to cast Ivy or Karen in the lead role for tonight's preview, the decision which could affect the show's future. Karen is the official understudy, but the understudy, as is generally the case, does not rehearse the role until after the previews have been completed. And Ivy knows the role more comprehensively at this stage having been in the lead earlier in the project's history. This issue causes major dissension among the team. A decision is made, which only increases the tension within the creative team. It also causes a four sided issue between Derek, Karen, Dev and Ivy. Meanwhile, Ellis makes an admission to Eileen, which he did for what he believed the good of the show, but which Eileen may see differently. And Frank comes to a possible impasse in his relationship with Julia, regardless of Michael's presence or not and regardless of if she remains faithful.
- Eileen's public legal problem concerning financing the show is perhaps the biggest obstacle in "Bombshell" making it to Broadway. As such, many with the show look for other professional opportunities. Derek may have problems getting another job as Rebecca Duvall's false publicity statement that she quit the show due to unwanted sexual advances by Derek leads to other actresses claiming the same. After running into another former actress colleague, Ivy contemplates getting out of the business altogether. And Karen comes across a couple of bartenders who are writing a musical, the songs which Karen loves. However, the composer, Jimmy Collins, doesn't want Karen's help, he who seems to despise her and everything about her. Meanwhile, Eileen plans on crashing an American Theater Wing dinner, where she and the "Bombshell" team are personae non gratae because of their public problems. Eileen wants to prove to the theater community that they are still alive, kicking and more than ready to take Broadway by storm. Eileen needs Tom and Julia at the function, but it may take a small untruth for Tom to get bedridden Julia, still in a depression over the dissolution of her marriage, to the function.
- Personal relations between Tom and Ivy are still strained, into which Ivy brings the cast onto her side. Wanting to mend their friendship, Tom, at the last minute as he reminded of the date, asks his friend and Ivy's idol Liza Minnelli to provide a surprise to Ivy for her birthday later that evening. Beyond Ivy already having made arrangements with her cast mates to celebrate her birthday without Tom, the evening has the potential to be a disaster for all concerned, which includes Eileen and Richard, who are testing the waters of a personal relationship. Meanwhile, Jimmy and Karen have embarked on a sexual relationship, but Karen wonders if Jimmy not wanting to tell anyone about it is a red flag. And Derek contemplates being honest with Karen about his feelings for her. While these three struggle with their as of yet unknown romantic triangle - at least unknown to Karen - Scott, Julia and Kyle work on the show without them. Their close working relationship may reignite romantic feelings that had bubbled under the surface between Scott and Julia when they were friends many years ago, while the working process may give Kyle some confidence in working without Jimmy.
- It's "Bombshell"'s opening night, to which Eileen has provided tickets to the cast and crew of "Hit List". While trying to avoid any on-line chatter leading up to the opening, Ivy can't help but be affected by one comment that she is only a chorus girl not up to a starring role. Karen, on the other hand, isn't sure if she wants to see someone perform the role she voluntarily gave up. And even before the opening, Tom and Julia contemplate their next move, which may or may not be together as a team. Much of what happens will depend on the reviews, the Times' which may be the most important but the one which may be in jeopardy if only because of Eileen's disintegrating relationship with Richard Francis. Meanwhile, Jimmy contemplates telling Karen of his sordid past. He may be beaten to the punch as Adam hangs around more, he who is getting closer to Ana. And based on the fact that "Hit List" has sold out its entire run even before its first show, Derek and Scott contemplate taking the show to Broadway for this season, which would then place it in direct competition with "Bombshell".
- Jerry has taken production control of "Bombshell" away from Eileen because of her legal issues, although she and the show's cast and crew are unaware that he orchestrated the publicizing of her illegalities with Ellis' help. Eileen tries to figure out a way to remain part of the production team while not kowtowing to Jerry. Regardless, there will be no show if Julia can't provide a satisfactory rewrite, her job being on the line. Julia is excited about her latest draft, which was developed with Peter's help, leading up to its official read-through, that is until Tom voices his concerns to her about Peter's possible ulterior motives. Karen is excused from the read-through, which allows her to concentrate her time on helping Jimmy and Kyle bring the first act of their musical to the Fringe Festival. They decide to do a read-through of their own with Karen's friends in attendance. What Karen does not realize until that read-through is that she has never seen or heard Kyle's text, and has no idea if it matches the quality of Jimmy's songs. Meanwhile, comedian Terry Falls finally arrives to rehearsals to assume his lead role in "Dangerous Liaisons". He wants to bring his comedic sensibilities to the role and production, which sits uncomfortably with Ivy, who believes it could jeopardize this production, what she considers her big break.
- "Bombshell", "Dangerous Liaisons" and "Hit List" are all going through problems. Ivy asks Derek for advice on how to save "Liaisons" and/or her career if the show goes forward in its current direction as dictated by its star, Terry Falls. With "Bombshell", Eileen, who had the tie breaking vote - with Julia and Derek on one side, and Jerry and Tom on the other - decides to go with Jerry and Tom and go with an earlier, more commercial book draft rather than Julia's latest draft, which she and Derek feel is the best work she's ever done. In addition, Jerry wants to cut the first song Julia and Tom wrote for the show, and what Julia still feels is the emotional core of the show. And Jerry, who has just found out about "Hit List", informs Karen on the day of the first performance that her contract does not allow her to perform in the show, which if she decides to abide by Jerry's directive will leave Jimmy and Kyle in the lurch at the eleventh hour. These situations leave Derek, Karen and Julia with decisions about their future with "Bombshell". However, some discovered information may in turn affect the production.
- Karen and Jimmy's first night together is cut short by the arrival of her father, in town for a conference. Beyond believing that Karen is in a sexual relationship with Derek, he can't get over the fact that she left "Bombshell", a Broadway show, for experimental theater. His demeanor toward Karen and the men in her life is based on this perspective. Specifically with Jimmy, he may not be able to outrun his past, which he'd rather forget, as he becomes more famous. Meanwhile, Ivy is having parent issues of her own, with her Broadway diva mother, Leigh Conroy, coming out of retirement to accept the role of Gladys, Norma Jean's mother, in "Bombshell". Ivy and Leigh's relationship during rehearsals surprises Tom, who isn't quite getting out of them what he wants. Julia tries too hard to mend her relationship with Scott, who in turn may have a condition to the reestablishment of their friendship. And Eileen and influential New York Times Arts Editor Richard Francis consider moving their relationship from the professional to the personal.
- Both "Bombshell" and "Hit List" have important upcoming full run throughs. "Bombshell" is doing a "friends and family" performance before going into its first preview the following day, which coincides with "Hit List" doing a run through the same day for Richard Francis, who plans to write an article on the show. A multitude of technical problems in the "Bombshell" "friends and family" performance may end up delaying the first preview show, which Tom wants to avoid at all cost as he sees a delay in preview as a public declaration of failure. Tom does whatever he needs to in six hours to correct all the technical problems to be able to satisfy Eileen to go through with the preview as planned. One of those technical problems, a wardrobe malfunction, ends up being something that Eileen and Julia want left in, as Marilyn in the nude adds a sense of vulnerability to the character. They leave it up to Ivy to decide if she will agree to this change. With Tom feeling like he alone has to provide direction to rectify the "Bombshell" issues, Julia heads to "Hit List" to continue her dramaturg work for that show. Based on Julia's suggestion, Derek makes an important change to the show's structure, which Jimmy and Karen see as Derek getting back at them for their relationship. Are they correct as to Derek's rationale? These run throughs have an unexpected public outcome.
- Tom has been appointed director of "Bombshell" after Derek leaves the show. But Tom's style and vision doesn't mesh with Karen, with who the rapport becomes quietly but openly strained. In addition, Tom doesn't feel he can use Derek's choreography, and as such the new dance numbers are insipid, especially in Jerry's eyes. Eileen works behind the scenes to regain legal production control from Jerry, but even if she does achieve this goal, it may be too late for Tom, who may be fired by Jerry, especially as he still wants Derek back at the helm. Jerry's wish may become reality as Derek is having troubles letting go of "Bombshell" from his life. Julia does whatever she can to protect Tom in this situation. Meanwhile, "Liaisons" now has as its star a non-medicated and thus non-manic Terry Falls, but that still may not be able to save the production from a critical drubbing on its opening and thus imminent closure. But some within the production may not see that as a bad thing. And after its run at the Fringe, "Hit List" tries to move to an off Broadway theater, but the theater's new manager, Scott, who is an old friend of Derek's, requests that Jimmy and Kyle make some changes before he allows it to be performed on the theater's main stage. This directive does not sit well with Jimmy, who doesn't agree with it.
- The level of collaboration at "Bombshell" and "Hit List" are taking divergent paths. Derek has his big budget sensibility in directing "Hit List" and is able to stick to his vision within the limited budget. However, that vision doesn't sit well with Jimmy, who voices his opposition. Their relationship is further negatively affected by Derek's hands off statement concerning Karen, who doesn't know why Jimmy has not approached her romantically. On the other hand, Tom, now the director of "Bombshell", wants to please everyone, especially his new star Ivy, by listening to and incorporating their ideas. However, Tom's juggling act has its own problems, especially in trying to incorporate an idea more for his own personal rather than professional reason. Derek and Tom may have to find a common middle ground for both their productions to succeed. Meanwhile, Julia is trying to mend a fifteen year estrangement with Scott. And Eileen, who has regained production control of "Bombshell", is having problems trying to drum up any positive buzz around the production. With Tom's approval, Eileen embarks on what she believes is a newsworthy idea which will most directly affect Ivy for good or more likely bad.
- Although Bombshell is officially going back into unofficial rehearsals, Karen and Derek are still looking for other projects "just in case". Karen is still interested in helping Jimmy and Kyle get their musical at least to a stage where someone may consider staging it, with Derek being her go to person. While Kyle is optimistically hopeful that Karen can produce what she says in terms of a meeting with Derek, Jimmy is more skeptical. But Jimmy takes a risk to get some materials in preparation for that planned meeting with Derek. Derek on the other hand, turns to Veronica Moore for an unofficial audition to direct her new show, The Wiz, using a restaged number from Bombshell as that audition piece. But the fact that Jack and Julia have to change the show significantly based on a directive by Eileen may throw a wrench into Derek's plans. What's worse, especially for Julia, is that Eileen has hired Peter Gilman, a dramaturg, to give Julia advice, this move which Julia does not take lying down. Meanwhile, Ivy auditions for a new musical production of Dangerous Liaisons, and turns to Jack for advice and support on how to approach the role she covets.