Julian (The Film Seeker)’s review published on Letterboxd:
That's right, I'm only now seeing this.
There are clearly shades of teen angst and peculiarity that would appeal to the millennials in Donnie's peer group, so this film's cult popularity isn't surprising. This movie definitely caters to adolescents who hear a line like “Why do you wear that stupid man suit?” and say “Damn... that shit’s deep!” Richard Kelly's direction falls in the grand indie tradition of shoving massive amounts of flashy style down your throat, that, while entertaining, aren't always as potent as the film clearly wants to be. This comparison might make absolutely no sense, but my impression is that Kelly wanted to make a teen high school indie like Rushmore by way of The Shining.
The dialogue and acting from the minors are pretty stiff at times, although the time travel discussions with the science teacher are stimulating enough to maintain interest. And it's nice to see parents in a movie that talk to their kids like they're actual people, however brief these scenes may be.
But the biggest shock had to be how stacked the cast of Donnie Darko actually was. Of course I knew Jake Gyllenhaal was here, and I knew Jena Malone was in it, but Maggie Gyllenhaal? Drew Barrymore? Patrick Swayze? And even more impressively, bit parts for Seth Rogen, Ashely Tisdale and CRAZY STEVE?! I think I found the real reason for this film's cult status.