(2001) Don's plum

After numerous unsuccessful encounters in a bizarre cabaret, spacey Ian (Maguire) succeeds in snagging sunny, off-duty waitress Juliet (Meadow Sisto) to tag along to meet his friends at their weekly confab. Nervous Jeremy (Kevin Connolly) brings hitchhiker Amy (Amber Benson), while moody Brad (Scott Bloom) persuades recent bedmate Sara (Jenny Lewis) to attend. Only the trash-talking Derek (DiCaprio) is unable to scare up a date after numerous pleas on a clunky cell phone, arriving stag to the semi-circular booth but soon balanced out by Sara’s cheerful friend Constance (Heather McComb).

Once seated, the fun begins. Derek promptly offends Amy so much she stalks out, smashing Jeremy’s jeep with a baseball bat. An overweight black woman walking by and a greasy mechanic at the next table are made fun of, as is their ditzy yet scheming waitress, a pair of transients, the owner, and everybody else who comes into their sphere. The expletive-filled and increasingly overcaffeinated gab includes discourses on Nirvana, masturbation, the male G-spot and sex in general. Various unprintable drinking games are played that involve the telling of truths. Sara and Constance share a deep kiss.

Would-be actor Jeremy has an odd encounter with an attractive and aggressive female producer in the after-hours club attached to the diner, while Derek (who at one point dons false teeth, through which he smokes) has a physical confrontation with Sara, who’s fighting a secret drug problem, on a secluded banquette. Brad is outed as maybe bisexual. A disagreement between Ian and Jeremy results in a predawn fistfight, after which they all wander down the deserted boulevard. Action is punctuated by brief, jagged bathroom interludes that find each character confessing or remarking on something directly into a mirror.(x)