Greg Proops (one of the most mind-warpingly quick-draw improv comics on earth) records the latest episode of his monthly Film Club podcast live — and then it’s time for Sideways. Greg sez: Andrew Payne’s sparkling, hysterical, buddy movie/road comedy/relationship screwball. A fading actor/scoundrel Jack (Thomas Haden-Church) and an obscure writer, mini-weasel Miles, (Paul Giamatti) were best friends in college and deeply have nothing in common. They decide to go to the not-even-Napa Wine Country for Jack’s big bachelor weekend before he gets married. The plan is some drinks, golf, and male-bonding. Jack is surprisingly reckless so the plan implodes when they run into Maya (Virginia Madsen) and Stephanie (Sandra Oh), and the madness begins. Lies, deception, an insanely long novel, kinky and naked married men chasing cars, desperation, drinking, failure, an intolerably happy ex-wife, parking lot beat-downs, stealing from Mom’s purse—this movie crams it all in one weekend, with loads of candid slapstick for the discerning viewer. You will never order Merlot again.

Dir. Alexander Payne, 2004, 35mm, 126 min.