“Today Is The First Day … Of The Rest Of His Weekend.” In this highly amusing (and criminally underrated) dark comedy directed by Miguel Arteta, naïve, sheltered insurance agent “Tim Lippe” (Ed Helms) travels away from his small hometown for the first time to represent his firm at an annual insurance convention (“ASMI”) in Cedar Rapids, Iowa. Once there, some seriously crazy shit goes down as convention veterans “Dean Ziegler” (John C. Reilly), “Joan Ostrowski-Fox” (Anne Heche) and “Ronald Wilkes” (Isiah Whitlock Jr.) teach uptight, uber-conservative Tim how to push the boundaries of good taste and enjoy life a little (which inevitably leads to a date with a prostitute named “Bree” and a trip to a crystal meth party!). As the foul-mouthed, hard-partying “Dean-Z,” Reilly steals the show: “Degenerate? I love it, that’s me!” The solid cast includes Stephen Root as Tim’s boss “Bill Krogstad,” Alia Shawkat as “Bree” and Kurtwood Smith as “Orin Helgesson.” Also look for Sigourney Weaver, as Tim’s former teacher, now love interest (he’s obsessed with her; she could frankly care less).
Useless Trivia: Arteta received the Independent Spirit John Cassavetes Award for his dark comedy Chuck & Buck (2000).