If you’re watching a film by writer-director Jonathan Goldstein ’95, expect the unexpected. It’s fitting, then, that Goldstein’s own life has been anything but predictable: After earning a degree in German literature, attending Harvard Law School, and practicing corporate law, he found success in Hollywood.
Known for blending humor with established conventions, Goldstein has earned praise for films including “Game Night” (2018), “Spider-Man: Homecoming” (2017), and “Dungeons & Dragons: Honor Among Thieves” (2023).
His latest film, “Mayday,” starring Ryan Reynolds and Kenneth Branagh and now streaming on Apple TV, continues that genre-bending tradition. It takes the familiar formula of the classic Cold War action movie, injects it with humor—and turns it on its head. Goldstein spoke to the Bulletin about his path from law school to LA, the making of “Mayday,” and the legal skills he still draws on as a filmmaker.
HARVARD LAW BULLETIN: What was your experience at HLS like?
JONATHAN GOLDSTEIN: I had brilliant teachers, and the people in my class were brilliant. But the classes I liked the most were the least legal in nature. For example, Larry Tribe taught an amazing class on biomedical technology and the constitutional issues it raised, which I found fascinating and philosophical. One day, Barbra Streisand came to our class. It was a happy day because I happened to be presenting on something, and I made Barbra laugh. I’ll always remember that.
I also had a friend and classmate on The Harvard Law Record, and we wrote a very tongue-in-cheek restaurant review column. He was writing a sample TV script with a partner in Los Angeles, and that was my introduction to how you get an agent. I had to go to law school to go to Hollywood.
After practicing corporate law for two years, you decided to head out to LA to try to make it as a screenwriter. What were those early days like?
They were terrifying. I knew I was taking a chance and that there was no certainty that I would succeed. But I approached it in a lawyerly way: Each day I tried to do at least one thing that would advance my goal of getting hired on a show. I was living in a very tiny, roach-filled apartment in West Hollywood, and reading scripts for an agency, which was a great introduction to the business. I read Variety and The Hollywood Reporter every day. I was around agents every day. I used the machines in the office to copy my spec script. Within six months I got a manager, an agent, and I was hired on a show. It was a quick but still scary transition.
Where did you come up with the idea for your most recent film, “Mayday”?
The basic plot is that an American pilot [Reynolds] is downed in the woods of Soviet Russia and is taken care of by a former KGB agent [Branagh], who agrees to help him get to Moscow. My filmmaking partner, John Francis Daley, and I wanted to do an action-oriented “two-hander” [a film with two main leads] in the style of “Midnight Run” or “Lethal Weapon”—those movies from the ’80s and ’90s that we love. We also wanted to say something about the state of affairs in America and its relationship with the rest of the world today, and a Cold War story felt like a good way to do that without being too on the nose or polemical.
Is there a common thread in the kinds of stories you are drawn to tell?
I like to find ways to do something that hasn’t been done before. Hitchcock has this great quote—that film should play the audience like a piano—and I love the idea of manipulating the audience into thinking they know where the film is going, and then turning that on its head. I also like mashing up genres in an unexpected way. With “Game Night,” my filmmaking partner and I blended a thriller with a studio comedy. With “Dungeons & Dragons,” we combined high fantasy with comedy. And in “Spider-Man: Homecoming,” we did John Hughes by way of a superhero movie.
How do you connect the skills you gained at Harvard to your work in the film industry?
I am one of the few people out here who actually looks at their contracts, much to the annoyance of my fantastic lawyers. Sometimes, I even catch something they didn’t notice. I also think in a much more strategic way about deal-making than many creative people do. I can’t help it—it was built into my brain in law school. These are skills you carry with you for life.
What advice would you give a law school student or alum who is considering a major career change like the one you made?
You have to be honest with yourself and ask: What is my passion? What do I want to spend my life doing? For many people, there’s great work to be done in the law. But for people like me, it wasn’t right, and the sooner you can get to that place, the better chance you have of making a big switch. I knew that if I didn’t try, I would look back and regret it, and I never wanted to be in that position.
