Sideways Poster

Sideways (2004)

123 min.
Plot  Miles Raymond is an aspiring – but unsuccessful – writer, a wine aficionado and a divorced, depressed, borderline alcoholic middle-aged English teacher living in San Diego, who takes his soon-to-be-married actor friend and college roommate Jack Cole, on a road trip through Santa Ynez Valley wine country. Though still occasionally recognized, Jack's acting career appears to have peaked years ago, when he co-starred in a popular TV soap but now does commercial voice-overs and plans to enter his future father-in-law's successful real estate business after he's married. Miles wants to spend the week relaxing, golfing, enjoying good food and wine; however, much to Miles' consternation, Jack is on the prowl and wants one last sexual fling, before settling into domestic life.

In the wine country, the pair visit Miles' favorite restaurant, The Hitching Post II and meet Maya, an attractive waitress with whom Miles is casually acquainted. Jack senses that Maya is interested in...



Paul Giamatti
Miles Raymond
Virginia Madsen
Maya Randall
Sandra Oh
Marylouise Burke
Phyllis Raymond
Jessica Hecht
Stephanie Faracy
Stephanie's mother
M.C. Gainey
Cammi's husband
Alysia Reiner
Christine Erganian
Phil Reeves
Dr. Walt Hendricks


All Titles

English Original Title

Release Dates


United States



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