How Winnie Holzman Bewitched Show Biz

Winnie Holzman has a career that most writers wish was theirs.  

For starters, she is a writer who has been working and selling her work consistently since 1987. That’s the year she impressed “Thirtysomething” show creators Marshall Herskovitz and Ed Zwick with her talent, and they hired her to write for their landmark show.

From there, she’s continued to write for television, not to mention film and theater. Holzman even created her own  TV series in 1994 entitled “My So-Called Life.” (Amongst other great attributes of the show, Holzman’s choice for the lead was an unknown by the name of Claire Danes.)

The prolific writer has penned Broadway musicals, too, including the book for Wicked in 2003. That behemoth of a hit is still selling out the Gershwin Theater on Broadway 22 years hence, and Holzman adapted the whole shebang for the big screen last year with Dana Fox. Working with director John M. Chu and composer Stephen Schwartz, the film became a phenomenon, taking in over $750 million worldwide and nabbing numerous accolades, including ten Oscar nominations. It won two, and just so happened to be this critic’s pick for the Best Film of 2024.

Holzman is also an actress, a producer, and happens to have one of Tinsel Town’s strongest and longest-lasting marriages. She’s been married to veteran character actor Paul Dooley since 1984. They have a daughter in the industry, too—Savannah Dooley—a successful screenwriter and television producer in her own right.

So, suffice it to say, I was excited to speak with one of my idols and am delighted to tell you that the legendary scribe could not have been nicer and was very happy to share her thoughts with readers of Pipeline Artists. We discussed her approach to writing, various highlights on her resumé, and what audiences can expect from the Wicked sequel, opening this November entitled Wicked For Good.

(NOTE: This interview has been edited for length and clarity.)

Jeffrey York: Winnie, do you know what you plan to write when you sit down at your computer via extensive planning, prepping and outlines, or is your process more spontaneous than that?

Winnie Holzman: It can vary from project to project. Each one has its own reality, aspects, and sets of challenges. Sometimes I collaborate with others, other times I’m starting on something all by myself. But in general, I like to have some kind of structure. When I was writing a play that got produced last year at Princeton, it was a play I had been working on for many years on my own and consisted mostly of random ideas or scene thoughts I’d had. It eventually evolved into something with structure and shape, but generally, I write with a clear sense of where I want to go with whatever I’m working on.

York: One of the hallmarks of your writing, particularly in the shows you’ve written for, like “Thirtysomething,” “My So-Called Life,” and “Once and Again,” is how grounded they are. They feel so real, lived in and accurate. They’re so eminently relatable. How do you cultivate such honest, truthful writing?

Holzman: A lot of it I learned while working with Marshall and Ed. They really broke ground with their more realistic approach to examining the way people live and work in the modern world. Also, for me, it was a way to transfer the experiences I’d had in my own life—those experiences that I thought others would be able to relate to or likely had gone through something quite similar themselves. When I write, I want to make a connection like that with the viewers. Even in something like Wicked, which is a fantasy, we wanted the struggles, the friendships between the two women, and their hopes and dreams, to feel relatable and true to people in the audience.

York: The dread that filled seasons two and three of “Thirtysomething” was palpable. Not just in the ad agency dynamics between main character Michael (Ken Olin) and his boss Miles (David Clennon) but in how Michael brought his doubt, angst, and worries home with him to his family each night. Tell us about that.

Holzman:: We wanted to show how all that drama at work affected every aspect of Michael’s life. Joseph Dougherty, who wrote those agency episodes, captured all that tension. It was all part of Michael’s struggle to fit in. It was something all the writers tried to do when working on “Thirtysomething.” That tension, that uncertainty of whether this generation fit in or not, that was the show. And we were living that in our own lives and helping translate those feelings to those watching at home and feeling the same way.

York: How did you get involved with Wicked?

Holzman: Composer Stephen Schwartz asked me personally to do the show with him, and we collaborated together from the start on its structure, the beats in the drama, where the songs should go. We discussed Gregory Maguire’s book and how it could be done for the stage. Stephen and I shared a very compatible point of view on the approach, so we started outlining together. We asked ourselves, “Where were the high points and which of those should have a song?” And when you write with someone as brilliant as Stephen Schwartz, you know he has such a great sense of language because of his lyrics, and he knows where the book should go and where a song should instead.

When it came time to adapt the musical to the movie screen, we wanted to stay very true to all that we had created for the stage and that had worked out so well there. However, with the advantages of cinema, we wanted to add even more grace, more elegance, more depth, and more brevity to the adaptation.

York: Such depth that you added to the story for the screen is obvious from the get-go. Galinda (Ariana Grande) is a much sadder character at the star of the film than in the Broadway show. And when she’s handed that torch to light the pyre of the Wicked Witch, the action you’ve written there, along with Galinda’s reaction to burning her friend in effigy, is devastating. It brought tears to my eyes two minutes into the film.

Holzman: It was really important for us to add those moments. We didn’t want to squander the opportunity to retell our story for the screen, and make more of the time we had and the intimacy of film. We made so many discoveries through the various drafts, and even though there was a long, leisurely build- up over the years where I was drafting it for the screen, when John came onboard and made the decision to break the story into two movies, things really changed. Now, we had the opportunity we were hoping for: the luxury of time to add all that more to the story. We could save all the musical numbers, give each scene more moments to increase the depth, and let it breathe to feel all the more cinematic. All that would let the two films be new experiences for the viewer, no matter how much they knew beforehand.

York: Did you feel pressures to please that fan base of the Broadway show—some who’ve seen the show dozens of times over the 20 plus years?

Holzman: We wanted the fans of the show to feel like they were getting a new kind of experience with the movie, like the show, but very different, too. And we wanted people coming to the film to enjoy it without having to see the Broadway production. We wanted everyone to get a new and positive experience from the films, all on their own, no matter how people were coming to them.

York: On Broadway, a character like Madame Morrible is a more obvious villain, as she needs to come across quicker given the time frame and the need to translate the show to the balcony. But in film, you get closer, have more time to be nuanced, and the character you wrote for Morrible (played by Michelle Yeoh) feels again, more real and grounded—one of the hallmarks of your writing.

Holzman: On screen, we were able to build more layers into the relationship between Morrible and Elphaba (Cynthia Erivo). We also deepened Morrible’s back story and her own disappointments in her career. Also, we wanted to make more of how Elphaba came to Shiz and how that could add depth to her relationship with Morrible, too. We looked at different ways of having Elphaba attend Shiz, like being her sister’s caretaker instead of an accepted student and then have her talents discovered by Morrible.

The whole time we were asking, “How can we make Elphaba’s journey even more interesting? How can we make more of her relationship with those around her? What would be more cinematic here or there?” I literally looked at every beat of the show and asked, “Is this written to be the most cinematic it can be?”

York: Do you do a lot of drafts?

Holzman: I do. I also write many versions of any given scene, too, so I can see what plays best. Sometimes I’ll write ten different versions of way to play things. And for Wicked, those scenes were influenced by what Stephen and I were trying to do to make it its own thing, as well as what John and Dana brought to the storytelling.

In the case of Elphaba’s friendship with Morrible, we wanted to make Morrible’s betrayal at the end of the first film be more devastating to Elphaba, and that is one of the reasons we started them off so close in our adaptation ... to strengthen Morrible’s turn for the worst in the third act.

York: You also shifted the character of Elphaba, too. On stage, she’s so raw and vulnerable, but on film, she’s more self-aware of her talents and power. It’s less about whether she, herself, will  recognize her worthiness, but more about whether others around her will.

Holzman: Erivo brought so much depth and bearing to the part too and that made the character have to be written different as well. Adding the scenes with Elphaba as a child also gave us the chance to show how she had to grow up faster with so much rejection and that would make her mature, too.

York: Galinda seems more self-aware as well. On screen, she seems to know that she’s really not all that special.

Holzman: It’s heartbreaking. Because Galinda is such a sad character in many ways. We got lucky with those two extraordinary women—Cynthia and Ariana—they really helped show those extra layers and give their characters more meaning. They themselves have such depth, such soul. And I think that they are both such masterful artists that such a level of artistry contains within it, a great vulnerability. And when you’re operating on that level, you’re dealing with performers who know how to be so open and expressive.

York: Did you see that in their auditions?

Holzman: I did. I remember when we were auditioning, those two women were the ones for me. We looked at a lot of talented people, and John wanted to really make sure we were thorough, but for me, it was Cynthia and Ariana from when I first saw them. They added so many additional aspects to their characters.

The production was already a big hit, so there was no need to do a movie, no point in doing a movie, unless we could really add to it, make it go even farther. Go deeper. And those two women had it from the beginning.

York: I love your dialogue in the new trailer when Elphaba tells Galinda, “You’re the only friend I ever had” and Galinda responds by saying,“And I’ve had so many friends … but only one that mattered.” It got me verklempt and speaks so strongly to what to expect in the new film. To that point, Winnie, is there anything you could tell us about the sequel, anything you want us to know?

Holzman: The trailer is very representative of the movie. And we’re very true to the second half of the stage show. We did decide to adjust some things to make certain parts more exciting, more emotional, but it’s a very faithful adaptation.

York: I know the film is still being put together, but is there anything you learned from the reception to the first film that might have helped sway the edit of the second feature?  

Holzman: The first movie has a lot of comedy, but then so does the first act of the Broadway show. But the second half of the show is less frothy, same with the film. But because the humor played so well throughout the first film, we are looking at ways to add more humor to the second movie in the editing.

York: When will you get to see the finished film?

Holzman: I’m hoping to see a finished cut from John later this month (July). And Stephen is still working on the score, too, so it’s still very much a work in progress. Also, Stephen has written  two new songs for the film, so there are definitely additions coming that will surprise audiences.

York: Finally, Winnie, what advice would you give to those wanting a career like yours?

Holzman: You have to be writing to be a writer. Wanting to be a writer is fine, but writing is what’s going to get you to be a writer. You have to be constantly working on your writing to get better and better. That means you do multiple drafts. You try to make every scene better. More interesting. Make your story clearer. Many people are writers who never get to have it be their profession, but they never stop writing. And part of being a writer is that willingness to keep going and keep getting better at it, even if you don’t make a living at it.  

I’d also say that when you’re doing what writers do, you’re facing constant rejection. Having a certain amount of success doesn’t keep your next project from being rejected. There has to be a higher calling to writing than just getting praised. It can’t be satisfaction from the outside. It has to come from within.

*Feature image created by Jeffrey York