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Sideways

Directed by Alexander Payne
R
2004    2h 7mDrama, Comedy,
7.597%79%7.1
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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 One is an unpublished novelist suffering from depression, and the other is only days away from walking down the aisle.

Where to Watch Sideways

Cast of Sideways

  • Paul GiamattiMiles
  • Thomas Haden ChurchJack
  • Virginia MadsenMaya
  • Sandra OhStephanie
  • Marylouise BurkeMiles's Mother
  • Jessica HechtVictoria
  • Missy DotyCammi
  • M.C. GaineyCammi's Husband
  • Alysia ReinerChristine Erganian
  • Shake TukhmanyanMrs. Erganian
  • Shaun DukeMike Erganian
  • Robert CovarrubiasMiles's Building Manager
  • Patrick GallagherGary the Bartender
  • Stephanie FaracyStephanie's Mother
  • Joe MarinelliFrass Canyon Pourer
  • Chris BurroughsChris at Stanford
  • Toni HowardEvelyn Berman-Silverman (voice)
  • Khoren BabouchianArmenian Priest
  • Lee BrooksKen Cortland
  • Peter DennisLeslie Brough

Sideways Ratings & Reviews

  • George BananzaJune 18, 2025
    Merlot loses its nobility.

Watch Sideways Videos

  • Sideways
    SidewaysTrailer
  • Sideways Scene: Are You Chewing Gum?
    Sideways Scene: Are You Chewing Gum?Scene
  • Sideways Scene: I'm Not Drinking Merlot
    Sideways Scene: I'm Not Drinking MerlotScene
  • Sideways Scene: Why Are You So Into Pinot?
    Sideways Scene: Why Are You So Into Pinot?Scene

 

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Sideways Trivia

Sideways was released on October 22, 2004.

Sideways was directed by Alexander Payne.

Sideways has a runtime of 2 hr 7 min.

Sideways was produced by George Parra, Michael London.

The key characters in Sideways are Miles (Paul Giamatti), Jack (Thomas Haden Church), Maya (Virginia Madsen).

Sideways is rated R.

Sideways is a Drama, Comedy, Romance film.

Sideways has an audience rating of 7.9 out of 10.

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