Written by: Alexander Payne & Jim Taylor
Starring: Paul Giamatti, Thomas Haden Church, Virginia Madsen, Sandra Oh, Marylouise Burke
Rating: [4/5]
For every enjoyable activity you can engage in, an enthusiast exists who goes beyond the mere pleasure of it and digs into it in a way others have no interest in. You could argue that’s me regarding films and having this blog, which I have no shame in admitting. With Sideways we get this deep dive into the world of wine all wrapped around a hilarious and thought-provoking story of two friends going out prior to one of them getting married.
Heading out to the Santa Ynez Valley wine country in California, enthusiast Miles (Paul Giamatti) takes out his soon-to-be-married friend, Jack (Thomas Haden Church) for a stag week. A week where they will visit different vineyards, go golfing, and enjoy their time together except when Miles learns Jack wants to have one last week of sexual deviancy prior to tying the knot.
As a casual drinker of wine who typically buys the cheapest bottle, not only does Sideways operate as an enjoyable movie but also an education about wine through the eyes of Miles. A man who has his own issues he must contend with like still struggling following his divorce but this hobby allows him to channel it through this love and knowledge for this alcoholic beverage. From the proper way to taste the wine and which grapes yield the best results. Miles speaks with such passion about this subject matter, which allows the comedic juxtaposition of Jack just chugging down the wine so funny. I try to imagine that’s what occurs in most conversations I try to have with others about movies where I try to dig deep about it and they just say they enjoyed it. Nothing wrong with that as I similarly would represent Jack in this story when it comes to wine as everyone has their one area they have an unbridled passion for.
This passion then gets intermingled when Jack insists he just wants to get laid leaving Miles in the position of trying to plan this week around Jack’s incessant need to have one last freedom spree before he promises to be an honest man. This leads them to meet Stephanie (Sandra Oh) and Maya (Virginia Madsen). They do some light double dating providing Jack the opportunity to do his pleasure-seeking and Miles to connect with a wonderful woman. This connection built between Miles and Maya makes for a special bond centered on the idea of wine and it gets quite illuminating.
A specific scene comes to mind where Maya goes on this monologue about what makes a specific bottle of wine special from the beginning of the process to the time you open it. She speaks on the evolution of wine and how it constantly changes and can be affected by something as innocuous as choosing the time to open it. Virginia Madsen delivers this monologue in such an alluring and passionate way and serves as the absolute apex of this movie and remains one of Alexander Payne’s finest pieces of writing in his entire career.
With a plot regarding deception and romance, you just know things will eventually go awry allowing for some heartbreak but also incredibly funny moments allowing Thomas Haden Church to deliver an all-time comedic performance. Everything this man says throughout the film was done in such a hilarious manner by this man. Almost operating as the antithesis to Miles in how he views the world, Church absolutely dazzles here but nothing compares to the exceptional work done by Paul Giamatti. Perhaps the most impactful performance of his illustrious career, Giamatti goes all in-in with his portrayal of this struggling man as he attempts to piece his life together despite everything in his head holding him back. The passion he has for wine borders on comedy at times where he delivers one of his best lines denigrating Merlot. I never knew someone could have such a disdain for a specific type of wine. It contributes to what makes Miles such a loveable character and Giamatti certainly does his part.
Watching anything done by Alexander Payne serves as such a treat and he creates something equally wondrous and hilarious with this story. The way he sets these characters up to have an impactful week allows for so many engaging moments where you feel the plight of these characters. He captures this particular wine area with such reverence and evidently made an impact on wine sales depending on the ones mocked and those adored by these characters. That’s the power of the movies I suppose.
Delectable in its composition and delightful in its execution, Sideways teaches and entertains as it brings these characters into the sophisticated world of wine. A film filled with so much passion and affection for something most people enjoy casually. This passion makes distinct scenes so impactful as Alexander Payne brings them together and the cast he assembles absolutely knocks it out of the park in creating a rich and gratifying viewing experience.
Films with Josh 
