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Last updated: 06 Jun 2026 at 13:00 UTC

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Review of by David L — 22 May 2010

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All movies begin with an open ended freedom where all paths are viable, but as each turn is taken progressively a course will dominate; this is inevitable. From infinite to finite. There is a crust of grief as the limitlessness is whittled away, as the world sets in it's unchangeable movie pseudo reality like engraved names on a reserved crypt. Sometimes a movie is able to hold onto the unkown bliss of creation, driving off the map with the unpredictability of actual life. This one took me there.

Miles (Giamatti) and Jack (Church) are dynamic and seemless in crisply written and fearless character studies. The writing swept me away, accepting defeat to its erratic offbeat tides. "You still seeing that shrink?" "I went on Monday. But I spent most of the time helping him with his computer.".

Miles owns the pessimistic realist, almost the super ego, while Jack is often the Id ("We're going to have some fun. Remember fun? We're going to have some of it. Okay?"), untamable, but a true friend who feels duty bound to free Miles from his mid-life, post divorce, unpublished struggling writer, maudlin meltdown. What a duo. Rarely have two actors synched so divinely, becoming a filament for the dialogue allowing one to see everything the author intended.

The film reveals the hazy, arguably nonexistant boundary between a sober, mature, corrosive reality and escapist immature euphoria. The two are a matter of perspective. Jack and Miles are two sides of the same equation. Jack: "You understand wine and literature and movies, but you don't understand my plight. And that's okay." Jack is about to get married closing off all avenues of bachelor fantasy escape, while Miles is free but alone; both positions seem equally terrifying. Jack is the invariably optomistic dreamer out to live every last drop of life, and Miles has accepted a bitter worldview with masochistic relish, "It's like you enjoy self pity. Makes you feel special or something." It's a simple inverse reflection, but rarely is it shown with such insane, dry, hilarious subversive clarity.

Sideways is a comedy about the reality of one's imagined failures and that you can never recapture the past, reminding us to drink that saved bottle of wine while it is still peaking. This is a transcendental road trip movie, a buddha-like journey searching for deeper wisdom in wine country, with a radiant script laying the pavement.

This review of Sideways (2004) was written by on 22 May 2010.

Sideways has generally received very positive reviews.

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