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  • Writer's pictureJohn Lim

MF 352 : Summer movie series : Sideways (2004)

Updated: Jun 16, 2022

We end the summer movie series with a trip to wine country and the 2004 classic, Sideways. More at

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Note: the summer movie series will air on Fridays.

Feel free to insert your own "like a fine wine" joke

I first saw Sideways (2004) on video. I was in a relationship at the time and one of our simple Saturday pleasures was going to Blockbuster Video to rent a movie. We had recently seen Napoleon Dynamite, which I thought was one of the funniest movies I've seen in a long time.

Sideways didn't impress me on that first viewing. I thought the characters of Miles (Paul Giamatti) and Jack (Thomas Haden Church) were insufferable and the dialogue struck me as pretentious and self-pitying. I fell asleep somewhere during their road trip to wine country and woke up to a ridiculous scene of Miles trying to retrieve Jack's wallet in a funny but awkward scene. Clearly, the movie didn't resonate with me.

About a year later, the aforementioned relationship was as much history as that video rental and as Blockbuster Video itself would be in just a few short years. The movie was playing on cable and I decided to give it another go. I watched it from beginning to end and while I didn't fall in love with it, I definitely had a greater appreciation for the film. By then, it had been a critical darling, sweeping up several major Oscar noms at the 2005 Academy Awards.

Today, Sideways is one of my all-time favorite comedies, and I dare say one of my favorite movies period. Somewhat ironically, my love for Napoleon Dynamite ended up being short-lived, a product of the early 2000s.

Between that second viewing and the recording of this week's episode; the final one of the 2021 summer movie series, I've had a many chances to revisit these characters on their trip to wine country. But it's only in recent years that I've come to appreciate the magic and the genius of the writing and the sublime acting. Somehow, this movie manages to take its subject matter of loneliness, despair, frustration and find a sweet spot that's thoughtful, insightful, and downright funny. Miles and Jack aren't best friends. I'm not even sure they're even really friends. Miles has written his magnum opus, the great American novel, and is now in a sit-and-wait purgatory for a call from his agent about a publishing deal. For Miles, this book is the one thing that has made his life of depression, failure, divorce, and mediocrity as a high school English teacher worth it. On the flipside, Jack is in denial about his glory days being in his rearview mirror. He's an actor who at one point was in several commercials and a "series regular" on a couple of shows. But now, he sits and waits for the occasional audition call while unenthusiastically contemplating his future father-in-law's invitation (i.e. mandate) to join the family real estate business. It doesn't help that Jack is a commitment phobe; engaged to a woman who is far more enthusiastic about their upcoming nuptials than he is. That Miles is friends with Jack, much less his best man at his wedding, seems improbable except that they were college roommates and neither of them have any other friends.

Miles decides to take Jack on a trip to wine country a week before the wedding. It's a nice, if not obligatory best man gesture plus a much needed respite as he anxiously awaits word on his book. Miles, a wine connoisseur, plans out a weekend of tastings, golf, and fine dining. Jack, however, sees this weekend as a chance to cut loose and have some last flings before he walks down the aisle and kisses his single days goodbye. Along the way, they stop at Miles's mother's house to wish her a happy birthday. Miles even brings a bouquet of flowers and agrees to stay for dinner, much to the chagrin of Jack. In one of the most funny and equally disturbing scenes, Miles sneaks upstairs to rummage through her drawers to find her secret Ajax can where she stashes her money. He peels off several hundred dollar bills, presumably to pay for the upcoming weekend. We're not sure whether to cringe or laugh so we do both. We also get a sobering moment as his glossy eyes scan the family photos; his silent visage hinting at some secret untold pain.

The next morning, Miles and Jack escape while his mother is asleep in front of the TV. They make their way to wine country when the story introduces us to two other characters. First is Maya (Virginia Madsen), a waitress at a local restaurant in Solvang. She's a graduate student studying horticulture and a wine enthusiast who's more than a match for Miles. During their first night, Miles and Jack dine at the restaurant where Maya recognizes Miles as a regular. As she deflects Jack's attempt at flirtation, it's clear that she's more interested in Miles. Soon after, we meet Stephanie (Sandra Oh), who Miles refers to as a "wine pour chick," at one of the wineries they visit the next day. She and Jack discover an instant chemistry that spells trouble for the upcoming weekend.

Sideways is a very apropos title as the weekend becomes an up and down adventure filled with wine, fine dining, infidelity, lies, subterfuge, ethical quandaries, love, and the aforementioned lost wallet. Throughout, we come to like and feel sorry for these characters, even as we despise many of their choices. It's the rare movie that can pull that off. In between, we're treated to stunning views of Southern California's wine country, accented perfectly by Rolfe Kent's score. While I didn't enjoy my first sampling, over the years my movie palette has grown to love this particular vintage with all of its complexities and textures. As Miles aptly describes:

"Then, I mean, oh its flavors, they're just the most haunting and brilliant and thrilling and subtle and... ancient on the planet.”

While he's talking about Pinot, it's also a fitting description for Sideways (2004).

The good:

  • Excellent performances from a stellar cast, notably Paul Giamatti, Thomas Haden Church, and Virginia Madsen.

  • The movie is funny on multiple levels, ranging from dry and witty to slapstick and downright ridiculous.

  • Beautiful cinematography and lens work, including several montages of California's wine country that pay homage to movies and TV shows from past decades.

  • Wonderful score by composer Rolfe Kent.

The bad:

  • If you're like me, this may take more than one viewing for this movie to grow on you. This is not a criticism so much as a disclaimer. I hated this movie the first time I saw it. Over time, as I came to love and appreciate it, it became one of my favorite comedic films and one of my favorite films in general.


  • The movie hurt Melot sales for a while after its release.

  • In one of the funniest scenes, Miles and Jack end up at a winery called "Frass Canyon," which was filmed at the real life Fess Parker vineyard. Jack is impressed while Miles decries it as overly commercial, at one point insulting their vintages as filled with "crushed up leaves and insects." Frass means insect excrement.

  • 16M budget, box office of 109.7M worldwide.

  • Other actors considered for the role of Jack include Matt Dillon and George Clooney.

  • Several oscar noms, including best picture, director, adapted screenplay, and supporting actor (Church) and actress (Madsen).


  • ***** (out of five)

Where you can watch Sideways (2004)

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