Since its initially tiny theatrical release in the fall of 2001, Donnie Darko has become one of the cult hits of the early millennium, known for its eerie, mind-bending plot and for its cadre of young actors who went on to become household names. The film solidified Jake Gyllenhaal’s status as a breakout star, transitioned Jena Malone out of child stardom, and introduced fans to Jake’s sister, Maggie Gyllenhaal, in what was only the second significant role of her film career. (She’d previously had a memorable supporting turn in another cult film, John Waters’s Cecil B. Demented.)
In the latest episode of the podcast I Think You’re Interesting, Vox critic at large Todd VanDerWerff engages Donnie Darko’s director Richard Kelly in a wide-ranging discussion about his career and his philosophical approach to filmmaking.
In the middle of the interview, a detour about the casting of Donnie Darko yields this interesting anecdote from Kelly about how Maggie Gyllenhaal landed her now-famous part in the film, alongside her brother:
VANDERWERFF: How did you end up casting the siblings? Because that’s a really great aspect of this film to me — they are believable as those characters, but … also believable as siblings because they are in real life.
KELLY: Well, once we realized it was going to be Jake and we were casting the rest of the supporting players, Joseph Middleton, our casting director — I have to give a lot of credit to him on advising me about a lot of these young actors — he said, you know, Jake has an older sister Maggie, and she’s done a lot of theater. She had a tiny cameo in a John Waters film. But she’s going to be a big name, and she’s going to be a big deal. Maybe consider her to play Elizabeth Darko.
And I’m like, well, that sounds like a great idea, because if she’s really as talented as you say, let’s get the real sister to play Donnie’s sister. What a gift that would be.
So I went and met with Maggie, and immediately, she was like, Richard, you’re only offering this to me because I’m Jake’s big sister. You should be finding the best actress for the role. So she was already trying to talk me out of casting her, in a very selfless way. And I was just really impressed by that, and by how strong-willed and determined — she immediately, she presented herself in such a way. So I was really determined to convince her to do it after that.
And I just knew that it was not a substantial role on the page, and the character is sort of tangentially involved in the plot in ways that you discover a little deeper if you look closer at the film. But her impact and her presence was so important in anchoring the sibling dynamic with Jake, which was significant. And, I think, with Mary McDonnell and Holmes Osborne and Daveigh Chase — they’re sitting at that dinner table with real siblings with a profound connection.
And so, Maggie was really an essential piece of the puzzle that makes that family dynamic work in the film. I’m grateful that she agreed to do the role.
For Kelly, though most of the plot was focused on Jake Gyllenhaal’s character’s (possible) descent into madness, the family dynamic that both Jake and Maggie brought to the film was crucial to its central theme of generational conflict.
“The first line of dialogue was ‘I’m voting for Dukakis,’ delivered by Maggie Gyllenhaal in the whole story, in that dinner table scene,” Kelly told VanDerWerff. He continued:
So I knew right away I was presenting a family that was at an intergenerational crossroads of Republican, Reagan-era parents who were fundamentally decent and empathetic people, and their children are taking a clear liberal diversion. Two roads are diverging within a family. But they all still love each other and they respect each other and care about each other deeply.
I knew right away that that was going to be an issue for the dynamic of this family … It’s gotta be about 1988. It’s gotta be about the end of the Reagan era and a generation that’s rejecting a lot of those policies and ideologies that you see even in the high school system.
Kelly also shared that when filming Donnie Darko, he was more inexperienced than most of his then-teenage cast. “I was a first-time director … and I was terrified of disappointing them or misrepresenting them or rendering the film poorly,” he said.
Still, he knew even then how to win an actor over: Give them a challenge.
“At the same time,” he said, “I want to challenge them and make sure that they are doing something slightly outside of their wheelhouse, or something new, and that they are stepping outside of their comfort zone at least once when they are playing this role. Because I think that’s what exciting, is when you can push someone into a new space.”
You can listen to I Think You’re Interesting on Apple Podcasts and Android’s podcast app, or at its official page. To hear more interviews with interesting people from all branches of the entertainment industry — from powerful showrunners to web series creators to documentary filmmakers — check out the I Think You’re Interesting archives.