Two middle-aged men embark on a spiritual journey through Californian wine country. One is an unpublished novelist suffering from depression, and the other is only days away from walking down the aisle.
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Paul Giamatti as Miles
Thomas Haden Church as Jack
Virginia Madsen as Maya
Sandra Oh as Stephanie
Marylouise Burke as Miles's Mother
Jessica Hecht as Victoria
Missy Doty as Cammi
M.C. Gainey as Cammi's Husband
Alysia Reiner as Christine Erganian
Shake Tukhmanyan as Mrs. Erganian
Shaun Duke as Mike Erganian
Robert Covarrubias as Miles's Building Manager
Patrick Gallagher as Gary the Bartender
Stephanie Faracy as Stephanie's Mother
Joe Marinelli as Frass Canyon Pourer
Chris Burroughs as Chris at Stanford
Toni Howard as Evelyn Berman-Silverman (voice)
Khoren Babouchian as Armenian Priest
Lee Brooks as Ken Cortland
Peter Dennis as Leslie Brough
Alison Herson as Foxen Winery Pourer
Phil Reeves as Vacationing Dr. Walt Hendricks
Rob Trow as Obnoxious Golfer
Lacey Rae as Los Olivos Waitress
Cesar Ramos as Barista
Daniel Rogers as Reciting Eighth Grader
Natalie Carter as Siena
Simon Kassis as Mini-Mart Owner
Sevag Kendirjian as Armenian Deacon
Jaren Coler as Acoustic Guitarist
Chris Astoyan as Mrs. Erganian's Son (uncredited)
JR Garcia as Little Boy (uncredited)
Gregory Heath as Tasting Room Customer (uncredited)
Alex Kalognomos as Alex (uncredited)
Parker Quinn as Customer in Shoe Store (uncredited)
Mikael Sharafyan as Armenian Wedding Guest (uncredited)