A wine tasting road trip to salute Jack's final days as a bachelor careens woefully sideways as he and Miles hit the gas en route to mid-life crises. The comically mismatched pair, who share little more than their history and a heady blend of failed potential and fading youth, soon find themselves drowning in wine and women. Emerging from a haze of pinot noir, wistful yearnings and trepidation about the future, the two inevitably collide with reality.
Production Fox Searchlight Pictures; Michael London Productions; Sideways Productions Inc.;
Cast Names Paul Giamatti; Thomas Haden Church; Virginia Madsen; Sandra Oh; Marylouise Burke; Jessica Hecht; Missy Doty; M.C. Gainey; Alysia Reiner; Shake Tukhmanyan; Shaun Duke; Robert Covarrubias; Patrick Gallagher; Stephanie Faracy; Joe Marinelli; Chris Burroughs; Toni Howard; Rev. Fr. Khoren Babouchian; Lee Brooks; Peter Dennis; Alison Herson; Phil Reeves; Rob Trow; Lacey Rae; Cesar Ramos; Daniel Rogers; Natalie Carter; Simon Kassis; Sevag Kendirjian; Jaren Coler; Chris Astoyan; Alex Kalognomos; Logan Mulvey; Parker Quinn; Mikayel Sharafyan;
Box Office USD 71,502,303
Release Date 2004-10-12 (Beverly Hills, California) (premiere) 2004-10-14 (Austin Film Festival) 2004-10-17 (New York Film Festival) 2004-10-19 (Austin Film Festival) 2004-10-19 (Chicago International Film Festival) 2004-10-22 (limited) 2004-10-23 (Savannah Film and Video Festival) 2005-01-21
Genres Comedy; Drama; Romance;
MPAA Rating [?] Rated R for language, some strong sexual content and nudity.