It’s been a long year, friends. We are near its conclusion and we all hope you’re staying sane, safe and well out there. To even the most casual Midwest Film Journal reader, it will be no surprise that we love puns around here almost as much as we love thoughtful, entertaining criticism and monthlong series that can highlight some of our favorite creators and creations. We thank you for another great year with us here at MFJ. So in that spirit that we hope makes you smile, our December ode to one of our favorite sibling duos: Deck the Gyllenhaals.

Lauren Emily Whalen lives in Chicago and is a 2018 alumna of the National Critics Institute and author of the 2021 novel Two Winters. Follow her on Twitter @laurenemilywri.

I have a soft spot for chaos.

When it comes to early-aughts writer-directors, you couldn’t get more chaotic than Richard Kelly. Consider 2007’s Southland Tales, an absolute masterpiece of mess. After seeing it not far from where it was filmed, I’ve described the movie to people as “Richard Kelly consuming every nightmare he’s ever had and vomiting it on celluloid. Also, Justin Timberlake.” For a brief time, Kelly shone wacky-bright in mainstream-ish Hollywood before burning out, taking his oddities with him.

My desert-island favorite Kelly also happens to star Jake Gyllenhaal: 2001’s Donnie Darko, which had a brief post-9/11 theatrical run before blowing up on DVD. Anyone who used the word “emo” as a self-descriptor even once during that time was obsessed with Donnie Darko. They sang its strange praises to everyone they encountered at parties, at work, at rehearsal. They briefly carried around the DVD with them like a goth security blanket. They listened to the heart-wrenching “Mad World” cover that accompanies the end of the film on repeat, while crying. (Just me?)

Donnie Darko was, as the kids say now, a vibe. And Jake Gyllenhaal was the perfect actor to star in it. He didn’t just radiate early-aughts chaos with mussed hair, an adorable mole and piercing eyes that projected private-school teen angst through the screen. In many ways, Jake was a more niche Tobey Maguire. They had similar coloring and were up for the same roles, even. But while Tobey edged out Jake for Peter Parker, sweet face everywhere as he transformed from borough nerd to Spider-Man, Jake’s Donnie was 1980s Reagan-era medium-cool and possibly schizophrenic, almost masturbating during therapy and surviving a plane crash into his own house while being haunted by a terrifying, yet kind of funny, rabbit named Frank.

Chaos.

It’s hard not to love a film with the opening line “I’m voting for Dukakis” (courtesy of Gyllenhaal’s real-life sister, Maggie, who plays Donnie’s older sister, Elizabeth, a Yarn Barn employee slash future Harvard student) and, when you are a 22-year-old recent college grad who has no idea what the hell to do with her life, harder still not to love Donnie. He’s smart but not annoying about it, he chirps happily about his emotional problems to new girl in school Gretchen (Jena Malone) and, best of all, he doesn’t take shit from authority figures, particularly Kitty Farmer (Beth Grant), teacher and Sparkle Motion dance coach, and Jim Cunningham (Patrick Swayze), the weirdly tanned guru with whom Kitty has become obsessed and who insists every emotion can be boiled down to “fear” or “love.” Sure, Donnie calls his mom (Mary McDonnell) a bitch, but that just gives him nuance.

As Donnie Darko, Jake Gyllenhaal is early-20s and early-aughts chaos personified. He knows his life experience can’t fit into neat little boxes. He respects his more jaded and intellectual teachers (played by Drew Barrymore, also an executive producer on the film, and Noah Wyle) even when they don’t give him the answers he wants about time travel. (Yes, time travel is part of Donnie Darko as well.) And when Frank the six-foot-tall rabbit shows up, asking Donnie about portals and “stupid man suits” with empty eyes and a maniacal grin, the teen doesn’t blink an eye. Instead, he wears a weird little smile that’s both mesmerized and smug. He knew it. There’s more out there.

It’s a strange movie, and in a lot of ways, Jake Gyllenhaal’s a strange actor: kind of mainstream but not quite, gracing the occasional blockbuster but never a superhero (basically a feat these days), forever choosing the interesting over the profitable even when it bites him in the ass. He grew up in the Hollywood scene, the son of a director and screenwriter and godson to Jamie Lee Curtis. As a young kid, he played Billy Crystal’s son in City Slickers. After graduating from a Los Angeles prep school, he followed his older sister to New York, attended Columbia University for two years and worked as a sous chef before breaking through in 1999’s October Sky, a heartwarming true story and the polar opposite of Donnie Darko. 

I know all these details off the top of my head because at the time I was not only obsessed with Darko but with Jake Gyllenhaal. Now I wonder if those eyes of his are soulful or vacant, and if he really had to be that much of a dick to Taylor Swift. But back then all he had to do was look at the camera and I was a goner. He wasn’t a lovable goofball like Maguire or an intimidating icon like Ewan McGregor; no, Jake was both dreamy and accessible. After all, Donnie Darko and most of his other filmography at the time were considered cult at best. He wasn’t known to the whole wide world (and I’ll admit even now, that’s still pretty sexy).

Best of all, he made cool choices like Donnie Darko. It’s not every star on the rise who probably says to himself or his agent, “Hey, playing a Reagan-era high school boy tormented slash befriended by a six-foot-tall bunny sounds awesome!” Even though I’m not 22 anymore, I still like to think Jake Gyllenhaal went with the role because it was unexpected. Donnie wasn’t making his own spiderwebs, but he was figuring it out: life with two sisters and parents who didn’t get him, a possible new girlfriend, teachers who displayed insight and spat bullshit in the same day, and what was likely a severe mental illness at a time when that was not discussed in public. All that and trying to make a portal because your imaginary friend said you should. It’s a lot, but Donnie was willing to take it on. Both character and actor embraced the chaos around them, something I deeply wanted to do at the time but wouldn’t figure out how for years yet.

I haven’t seen Donnie Darko since I did a midnight lecture on the film in 2011. I’d eked through my 20s by then, and life wasn’t as chaotic anymore; at that point, I was just happy to geek out about deleted scenes with others who could never get the movie out of their heads. I considered revisiting Donnie Darko for this piece, but honestly? I don’t care if it holds up. Like Southland Tales, which kept me company in L.A. as I waited for my friend to finish his restaurant shift, the movie served its purpose. And though he’ll likely never know, so did Jake.