Sideways

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

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

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

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

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

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

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

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

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

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

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

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