8. Donnie Darko
On a budget of $4.5m, Donnie Darko couldn't even recoup that small amount, bringing in only $4.1m, despite starring popular actors like Drew Barrymore and Patrick Swayze. It helped launch the career of not only lead Jake Gyllenhaal, but writer-director Richard Kelly, who hasn't exactly had the most dazzling career since - directing Southland Tales and The Box - but has remained an enigmatic and mystifying figure of cult cinema since. With its quirky premise and unfamiliar leads, it's perhaps not too surprising that the film didn't do massive business at the box office, but its wide acclaim probably should have been able to at least net it its money back. Still, on home video, the film has been a huge hit, such that a Director's Cut re-release happened in U.S. theatres, even if it didn't end up making a whole lot more than (which contributes to its $4.1m gross). It's a cult classic, though its somewhat esoteric nature doesn't make its failure that much of a surprise, especially when we consider its small distribution.