Donnie Darko

Written and directed by first-timer Richard Kelly on a $4.5 million budget financed through Drew Barrymore's production company Flower Films (Barrymore also played teacher Karen Pomeroy), Donnie Darko premiered at Sundance on January 19, 2001, and was released October 26, 2001—just six weeks after the September 11 attacks. Its marketing featured a crashing plane, so the film was scarcely advertised at all. It played 58 theaters at its widest release and grossed just $517,375 in its initial theatrical run—a commercial disaster that looked like a career killer.

Then came the resurrection. When the film hit home video in March 2002, New York's Pioneer Theatre began midnight screenings—and ran them for 28 consecutive months straight. US DVD sales brought in over $10 million, and theatrical reissues pushed the worldwide gross to about $7.5 million — the flop had become a genuine phenomenon. A Director's Cut premiered May 29, 2004, giving it new life among fans who'd spent years dissecting it frame by frame. Jake Gyllenhaal's haunted performance as troubled suburban teen Donnie, opposite James Duval's nightmarish Frank in the rabbit suit and a supporting cast including Jena Malone, Patrick Swayze (as motivational guru Jim Cunningham), and Gyllenhaal's real-life sister Maggie, locked in viewers' minds through pure magnetic weirdness.

The film's haunting cover of "Mad World" by Gary Jules and Michael Andrews (stripped down from the Tears for Fears original) became the UK's Christmas No. 1 in 2003, spending three weeks at the top—proof that Donnie Darko's mood had seeped into the cultural bloodstream. It became THE 2000s dorm-room cult DVD, the movie you borrowed from a friend with no explanation required, watched alone at midnight, and texted about obsessively the next day. It asked big questions about free will, alternate timelines, and destiny, wrapped in a surrealist package no studio would finance today.