Sideways

In search of wine. In search of women. In search of themselves.

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 One is an unpublished novelist suffering from depression, and the other is only days away from walking down the aisle.

Thomas Haden Church

Jack

Virginia Madsen

Maya

Sandra Oh

Stephanie

Marylouise Burke

Miles's Mother

Jessica Hecht

Victoria

Missy Doty

Cammi

Alysia Reiner

Christine Erganian

Paul Giamatti

Miles

Shake Tukhmanyan

Mrs. Erganian

Shaun Duke

Mike Erganian

Robert Covarrubias

Miles's Building Manager

Patrick Gallagher

Gary the Bartender

Stephanie Faracy

Stephanie's Mother

Joe Marinelli

Frass Canyon Pourer

M.C. Gainey

Cammi's Husband

Chris Burroughs

Chris at Stanford

Peter Dennis

Leslie Brough

Toni Howard

Evelyn Berman-Silverman (voice)