| Cast overview, first billed only: | |||
| Paul Giamatti | ... | Miles | |
| Thomas Haden Church | ... | Jack | |
| Virginia Madsen | ... | Maya | |
| Sandra Oh | ... | Stephanie | |
| Marylouise Burke | ... | Miles's Mother | |
| Jessica Hecht | ... | Victoria | |
| Missy Doty | ... | Cammi | |
| M.C. Gainey | ... | Cammi's Husband | |
| Alysia Reiner | ... | Christine Erganian | |
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Shake Tukhmanyan | ... | Mrs. Erganian (as Shaké Toukhmanian) |
| Shaun Duke | ... | Mike Erganian (as Duke Moosekian) | |
| Robert Covarrubias | ... | Miles's Building Manager | |
| Patrick Gallagher | ... | Gary the Bartender | |
| Stephanie Faracy | ... | Stephanie's Mother | |
| Joe Marinelli | ... | Frass Canyon Pourer | |
A week before his friend Jack is to be married, best man Miles and the prospective groom head off to wine country for a week of fun, relaxation and - of course - wine drinking. Miles is the oenophile and does his best to teach Jack a bit about the art of appreciating great wine. All Jack cares about is drinking and carousing, something he accomplishes when he meets the attractive Stephanie at one of the vineyards. Miles is something of a sad sack, a high school English teacher who is a failed writer at heart. He has yet to get over the fact that his wife has divorced him and that she has remarried and he now faces that nerve racking wait for word from a prospective publisher. Miles has an opportunity to start anew when he meets Stephanie's friend Maya but when he let's slip that Jack is about to be married any hope of a relationship seems to be lost. Written by garykmcd
Sideways is a beautiful portrait of mid life disappointment. The backdrop is lovely California wine country, and the casting is flawless. Every single performance in this film is surprising, pitch perfect, and unusual. The movie has the remarkable ability to capture sadness and desperation in just the light that allows the audience to recognize the humor. The ending is satisfying but not too pat. In short, this is the best film of 2004.
The standout performance in the film was Paul Giamatti's. I cannot believe he was passed over for an Oscar this year. He should have been nominated for American Splendor, and he definitely should have been nominated for Sideways. His performance was beautiful, romantic, heartbreaking and so human. Paul Giamatti, ignore the Academy! Every year they have less credibility. The people who know films and acting at all know that you are one in a handful of truly great actors working in Hollywood today.