Andy Bobrow: Hi again and thanks for coming everyone. It seems like we’ve established a theme here of talking about how the business is changing, so this week’s discussion is going to be the simple question: How did you ‘break in,’ and how have you stayed in? As of me typing this, I don’t have a guess as to whether we’ll see any similarities in the stories. Could go either way, so let’s just start.
Angela Workman: Ok, I’ll give it a go. I started writing in my early days in LA, after living and working as an actress in New York. I was trained with writers, was always a voracious reader, and it was thought that I’d be a good fit in film offices in my between-acting temp job days in NYC. I loathed temping, but I loved reading. I knew no one in Hollywood. I had no money and no help. I was entirely unfamiliar with screenplays. But when I discovered I could get paid a little bit to read them – and books, many many books, because I read fast and I wrote fast coverage – it seemed like a dream to me. I could work by myself at home (this is how I still work) and get paid (not very much – I was broke for a long time). I moved from NY to LA and became both a studio reader and agency reader. I realized that the puzzle of screenplay structure fit my internal wiring. I just instinctively understood it. I read thousands of scripts over about ten years, I consulted with writers and producers and was even an exec for a short while. I learned both what to do and what not to do (what not to do is at least as important as what to do, in my opinion). I started writing my own screenplays on spec. My second spec introduced me to my agent, who is my agent to this day.
Very early on, I wrote a small film loosely based on my mother’s life, that managed to get made in England (where she was from). That, and my specs, and my ability to pitch, got me into every room in LA. I sold all my pitches. But the twist, I guess, is that, once that happens a few times companies begin to bring you material, instead of the other way around. I could stop pitching as more and more material was submitted to me. I’ve had three movies produced. I’ve written for Spielberg (my very first sale), Fincher, Emmerich, Niki Caro, Stephen Colbert. I’m well established as a feature writer. But, interestingly, it’s a new age now. The demands of the industry have changed. I’ve never written a series and never cared to staff, because I like writing alone, in solitude. Material still comes in for me, but it’s slower, and momentum is harder to build and sustain. And as I’ve gotten older and more experienced in the business I’ve realized that I want to control my own stuff. Writing other people’s stuff isn’t nearly as fun or satisfying. So I’ve gone back to some original scripts, to polish them up for sale. I’ve been waiting to close a pilot deal, which I’ll create; it will be my first pilot. I still pitch on OWAs when they come my way. My agent is still my ally. I’m learning to pivot from theatrical to streaming, which is a little daunting. I still love big movies on big screens; I wanted to be like Robert Bolt, writing for David Lean. I come from the tradition of epic histories, epic wide-screen storytelling. I don’t know what that means for me going forward, but I’m sure the next few years will tell me. (A quick edit to say that today I told a producer, who has resurrected an old and beloved script of mine, that I don’t want it to go to the marketplace unless I’m attached to direct it. This would be a first for me; I nearly directed a film about the Bronte sisters, with Michelle Williams starring, but that fell apart at the 11th hour, sadly. I’ve dreamed of directing ever since. His reply was: “Fine, good by me.” It’s a long shot, I know – I’ve been here before, and I’m a realist – but don’t ask, don’t get, as they say. I think if feature writers are wise at all, and want to increase our power, we have to turn our attention to writing/directing, if even remotely possible.)
Flint Wainess: My break-in story started at a wedding. I had ditched my political science dissertation four years in to try to break into an industry I knew nothing about, with no contacts to help me. Predictably, it did not go well. But then, a beautiful wedding at the Plaza Hotel. Not mine, my friend Molly’s, where I was seated at the singles table next to the wedding columnist for the New York Post. She started telling me about her job and how, having just gone through a breakup, she wanted to murder most of the brides she was covering. I said there should be a breakup column next to the wedding column and a few weeks later we started a punchy little website that offered just that, and a few months later we sold a book about breakups. That book got me signed at UTA, and I developed a pitch for a TV show based on the book. One of the producers I pitched it to was Barry Josephson. He only had 20 minutes to hear it on his lunch break at Bones, and the room he was going to use wasn’t available, so I pitched it to him in David Boreanaz’s trailer while Boreanz watched the Yankees game. Four sentences in Barry said I love it, let’s go set it up at 20th. We did. And while it didn’t become a series it got me into the system, and I started selling pilots, then my first feature.
It didn’t take long to realize it’s extremely difficult to get your pilot shot if you’re not someone already firmly entrenched in the system, so I decided I needed to staff. I didn’t yet know that staffing is very often like high school, full of cliques and crushes and pointless late nights and all kinds of weird shit that has nothing do with writing television. While I didn’t last long in the world of staffing, I then did sell a pilot that got made (twice, long story) and then wrote a feature spec that sold and made the Blacklist and led to some other writing jobs (and also led to a great amount of bitterness and anger over what happened to that Blacklist script, but I’ll save that horror story for another Andy Bobrow prompt).
What I should have done to stay in the business and get rich is park on a show that has legs. My friends who staffed on a show that runs for multiple seasons were able to get rich eating snacks and being nice to the showrunner. You can go from staff writer to sought after CO-EP with an overall in a few short years if you play your cards right. You don’t even have to have written a script anyone likes, because the written by credit on TV series is so often meaningless.
Anyway, I didn’t do that because I’m an idiot. So how did I stay in? Specs. Every time my career has bottomed out, I’ve gone through many months of depression then fought my way out of it and written a new spec. It’s hard/painful/lonely work writing for free, not knowing if it will amount to anything, but most of the times I’ve done it it’s led to a new sale and new life. Which reminds me: gotta go start scroutlining (somewhere between a script and an outline) that new spec.
Marc Guggenheim: I’m the oldest of three brothers. My middle brother, Eric, was in his senior year of film school while I was in my “senior” (i.e., third) year of law school. Although he would go on to become a writer, Eric’s original intention was to direct. Nevertheless, he thought the experience of writing a script would be a useful exercise in that pursuit. He didn’t want to do so alone, however, and he asked me if I was interested in co-writing. I hadn’t done much creative writing apart from a few short stories, but I was game. I have to say, I really got bit by the bug.
Anyway, he graduated film school and I went off to practice law. But I found that I really enjoyed writing, so I kept at it. Because I was working weekends and was too spent from a day of litigating to write at night, I would wake up each morning at 5 AM to write for two hours before heading into work. By this point, Eric and I were writing separately, but we’d found a manager to represent us. I wrote a romantic comedy spec feature that got me a lot of meetings. I was practicing in Boston, however, and used my vacation time to come out to LA to take meetings.
Meanwhile, I was working 80-90 hour weeks as a litigator for a big firm which was, at the time, the oldest law firm in Boston. In that firm, you could go for junior partner in your sixth year of practice. By the time I was in my fifth year of practice, I realized I was quickly reaching the “fish or cut bait” stage of my career and decided to cut bait. The bloom had fallen off the rose of practicing law by that point. Plus, I became convinced that if I was every going to quit and move to the other side of the country, it was best to do so before I had a wife, three kids, and a mortgage. I was also spurred along by a passel of friends who basically turned my birthday party into an intervention.
My last day at the firm was in January of 2000. My office was a revolving door of partners lamenting that they wished they could do what I was doing but they had a wife, three kids, and a mortgage. I moved to Los Angeles on March 3, 2000.
This date was very deliberately chosen. I scheduled my move to coincide with staffing season, thinking that I had about a month to write my sample. However, the day I arrived in L.A., my manager said that she needed it by the end of the week. This was back when samples were specs of existing shows and I wrote an episode of The West Wing. I got the A-story from a bumper sticker I saw while I was leaving Boston. The B-story was inspired by a case I read in law school.
My manager sent the sample around to agents. The only one who responded was Matt Solo, who was at ICM at the time. He had just placed two clients on The Practice which – in a perfect definition of “right place, right time” – was looking to hire first year writers who used to be lawyers. (And I’d had over four years of experience practicing in the jurisdiction where the show took place.)
The head of David E. Kelley’s company at the time, Pam Wisne, read my spec and said, “David’s going to want to meet him, but unless he has two heads we’re going to hire him.”
My manager responded, “We’re chopping off the second head right now.”
And that’s how I got started. One year later, the firm where I had practiced which had been in business for over 150 years closed its doors. Any causal connection between that event and my quitting I leave for others to make.
AB: It’s so fun reading these, we’re going to make it a regular feature. And if you’d like to tell your story here, let us know through the Substack interface (I have no idea how to do that but there must be a way). For next week, we’re putting together a discussion on mini-rooms. Thanks for joining.