Sideways Cast
The cast of Sideways.
Paul Giamatti
as Miles

Paul Giamatti plays Miles, a wine enthusiast who struggles with his personal and professional life.

Thomas Haden Church
as Jack

Thomas Haden Church portrays Jack, Miles' carefree friend who is looking for adventure on their road trip.

Virginia Madsen
as Maya

Virginia Madsen acts as Maya, an aspiring waitress and wine lover who becomes an important figure in Miles' life.

Sandra Oh
as Stephanie

Sandra Oh plays Stephanie, a waitress who develops a romantic connection with Jack.

Marylouise Burke
as Miles's Mother

Marylouise Burke portrays Miles's Mother, who has her own views on life and relationships.

Jessica Hecht
as Victoria

Jessica Hecht plays Victoria, a character who interacts with Miles during his journey.

Missy Doty
as Cammi

Missy Doty acts as Cammi, who is in a relationship with one of the main characters.

M.C. Gainey
as Cammi's Husband

M.C. Gainey plays Cammi's Husband, who has a supporting role in the story.

Alysia Reiner
as Christine Erganian

Alysia Reiner portrays Christine Erganian, a character who is involved in the lives of the main characters.

Shake Tukhmanyan
as Mrs. Erganian

Shake Tukhmanyan plays Mrs. Erganian, adding context to Christine's character.

Shaun Duke
as Mike Erganian

Shaun Duke acts as Mike Erganian, who adds depth to the Erganian family dynamic.

Robert Covarrubias
as Miles's Building Manager

Robert Covarrubias plays Miles's Building Manager, providing a glimpse into Miles' daily life.

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)
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