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Title: Sideways (2004)
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| 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 | |
 |
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
Sad, disillusioned and depressed middle school teacher/aspiring novelist Paul Giamatti takes his best friend (Thomas Haden Church) to California's wine country for one last week of freedom before he marries. Church is on the prowl though and extremely horny as he wants nothing more than to sleep with women before his wedding. Thus these two opposites (who are more alike than they appear on first glance) have all sorts of adventures and misadventures. They meet two women (Virginia Madsen and Sandra Oh) and immediately take an interest in them. Divorcée Giamatti is shyly attracted to Madsen while Church falls in lust real quick with Oh. What is going to transpire over this week? Outstanding direction by Alexander Payne (who is one of the better "new-age" film-makers) knows which comedic and dramatic buttons to push here. His screenplay (which he co-wrote with cohort Jim Taylor) is deeper than it appears on the surface. Just like "Election" and "About Schmidt", "Sideways" works because the characters are quirky and hilarious, but also vulnerable and real. The four leads are remarkable with Church stealing the show and Madsen doing the work of her life. Giamatti's quiet and heartfelt role makes you sympathize and care for this flawed man. An intelligent adult-themed comedy/drama that works from many angles. 4.5 out of 5 stars.