How to Make the Cruelest Month is a 1998 comedy film written and directed by Kip Koenig and starring Clea DuVall.
The story centers on Bell, a young woman who resolves to accomplish her New Year’s resolutions—to quit smoking and to find love—before the end of December.
How to Make the Cruelest Month premiered at the 1998 Sundance Film Festival, where it was nominated for the Grand Jury Prize.
He also praised the ensemble cast and enjoyed DuVall's performance as the "tomboyish, neurotic Bell", although he noted the latter was "occasionally too intensely mannered."
Among Levy's criticisms of the film were its "messy structure and lack of discipline", which he said often characterizes filmmakers' debut features.