Jake Gyllenhaal's Best Role Was Given To Jason Schwartzman First

When it was released in January of 2001, Richard Kelly's bleak time-travel psychological drama "Donnie Darko" caused a notable stir. The title character, played by Jake Gyllenhaal, is a teen struggling with schizophrenia in 1988, a time when Reagan's great Conservative revolution was drawing to a close and adults clung to suburban conformity as it crumbled under them. Donnie is obsessed with time-travel and regularly hallucinates a vicious, strange anthropomorphic rabbit monster named Frank (all while attempting to socialize at school and foster a romance with a classmate played by Jena Malone). Patrick Swayze appears as a cheesy self-self guru, Drew Barrymore plays one of Donnie's teachers, and Maggie Gyllenhaal plays Donnie's sister.

By turns psychedelic and weirdly moving (in a Goth sort of way), "Donnie Darko" quickly became a cult hit and rotated directly into the local midnight movie circuit, attracting a wide swath of misfits and night people. It was voted one of the best indie films of all time by Empire Magazine, with Kelly being hailed as an important new voice in cinema. He drank his own Kool-Aid, however, and the director returned in 2006 with the sprawling and utterly ridiculous "Southland Tales," a jumbled treatise on the wild grossness of the George W. Bush years in America. "Southland Tales" is a trainwreck — and the train is full of clowns.

"Donnie Darko" gave a much nicer boost to Jake Gyllenhaal, already a recognized actor from Joe Johnston's gentle biopic "October Sky." After 2001, Gyllenhaal began appearing in notable film after notable film ("Bubble Boy," "Lovely and Amazing," "The Good Girl," "Moonlight Mile"), becoming a legitimate movie star.

According to an oral history published by The Ringer in 2021, however, the role of Donnie Darko almost went to Jason Schwartzman, who was coming off starring in "Rushmore."

Schwartzman, it should be noted, is a member of the extended Coppola film dynasty, making his involvement in the family business almost inevitable. He is the son of Talia Shire and the nephew of Francis Ford Coppola; Nicolas Cage and Sofia Coppola are his cousins. Wes Anderson's 1998 film "Rushmore" was Schwartzman's big break in film, and it began a longtime working — and personal — relationship between the actor and director. Schwartzman has appeared in five additional Anderson films since 1998, most recently in 2023's "Asteroid City."

Like Gyllenhaal, Schwartzman experienced a career boom in the early 2000s, showing up in indie films like "CQ" and "Spun," but also studio films like "Simone" and "Slackers." Schwartzman is only six months older than Gyllenhaal.

"Donnie Dark" producer Sean McKittrick and Richard Kelly both recall Schwartzman's audition (and how much they loved him) when interviewed by The Ringer. According to Kelly, the film's script had been passed around through Hollywood when Schwartzman asked to meet:

"God bless Jason Schwartzman. That meeting, he became attached. This is in late '99 or the very beginning of 2000. When Jason became attached, all of a sudden it legitimized me as a director."

Sadly, Schwartzman was unable to get out of his commitment to a previous film — possibly "CQ" — and had to drop out of the production in a hurry. Kelly panicked. He recalled the wild dash to audition any young actor he could:

"When we lost Jason, we met with every young actor in town. It was really exciting. I remember Patrick Fugit from 'Almost Famous,' we had a great meeting with him. Lucas Black from 'Sling Blade.'"

Luckily, Gyllenhaal had the script as well.

Back in 2016, Gyllenhaal was asked about "Donnie Darko" by The Guardian. He recalled with clarity reading Kelly's script and being blown away:

"I remember pulling over to the side of the road to finish reading Richard's script and being mesmerized. It was clearly influenced by classic directors – Ron Howard, Steven Spielberg – but with this strange psychosis. It beautifully captured the experience of moving into adulthood: the world that felt so solid becoming movable and liquid. I thought, 'This is what my adolescence felt like,' although I don't speak, and have never spoken to, rabbits."

Gyllenhaal also claimed responsibility for the casting of his older sister Maggie Gyllenhaal in the film. Both Jake and Maggie have enjoyed impressive careers, although Jake admitted that they had something of a rivalry back in their 20s. Maggie began acting professionally first, having appeared in several of her father Stephen's movies (Jake did that too, incidentally), as well as John Waters' under-appreciated "Cecil B. Demented." When "Donnie Darko" came up, Jake brought on Maggie, and the scenes where the two snipe at each other were, he said, authentic:

"It was my idea to have my real-life sister, Maggie, play my sister in the film. We were going through a competitive phase, which fed into the dinner-table scenes, where she tells me: 'You can go suck a f***.' Maggie was the reason I got into acting and is the more formidable of us. Yet I was the one who started my professional career first. Imagine being in a movie with your obnoxious little brother as the lead."

The 2009 sequel, "S. Darko," was made independently of either Kelly or Gyllenhaal.