Sideways: Fractal Pretentiousness

Faye Seidler
17 min readMay 23, 2021


I had originally watched Sideways on DVD somewhere in the mid 2000s. When I had watched it there was no cultural hype around it, I rented it from a blockbuster probably because it was a drama/comedy and why not. I didn’t think much of the movie, I didn’t hate it or love it. I was mildly disappointed, but it was engaging enough to not feel cheated out of my money. I never really thought about it after then and probably wouldn’t have except for one scene that I particularly liked that featured the main character drinking a fancy wine in a fast food establishment. The scene embodied to me the idea that one should not wait for something special to happen, but with intentionality they can create something special anywhere.

The day you open a '61 Cheval Blanc, that's the special occasion.

I had spoke about this Facebook and prefaced the story by acknowledging the movie wasn’t great. I had assumed at the time that everyone else had a similar experience. I was, in retrospect, hilariously trying to defend this movie as being meritable. I had never heard in my teenage years the great exalt put into this indie darling of 2004. I had never heard people reflecting on this masterpiece in 2010, 2015, 2020. It felt all but forgotten to time. So, I looked into Rotten Tomatoes and was absolutely shocked to see so much love showered onto this movie.

What was I missing? Metacritic too and every reviewer and site out there was singing the praise. What were people getting out of this movie that I wasn’t? I could understanding someone liking this movie. I could understand this movie being especially appealing to a number of people. It has that arthouse experimental feel critics eat up and that Emperor’s New Drink vibe that carries people for the ride. What I could not understand at all was why so many people would love it. Was it new to them? Had they not read enough Stephen King to get the feel of alcoholic writer character insert made hero? So, I tried to understand, because it’s so fascinating to me how discordant art can be between the different cultures and perspectives that form our lens.

I read through a number of reviews on this movie, but I couldn’t find any in-depth analysis. What I found where a plethora of credits waxing romantic about wine puns in the same pretentious vein of the movie. I was rarely looking at true critique, I was looking at conclusions. I was being told the acting was good, the story was good, the messages were beautiful. I wasn’t being told why or how, how it tied together — only that it felt like it did to the people watching. Some invisible rug tying it all together, making it work, completing the room, but otherwise lost to me.

As I explored further it all seemed so superficial. Of course Paul Giamatti is a phenomenal actor, yes the music is fantastic, yes the performances are what they need to be, but do these elements truly add together and what message do they tell? I am told this is a human experience, that the comedy exists in the bittersweet notes between longing and desperation. However, is what we are seeing so universal? Is this story the vehicle that delivers us to the human gestalt unfiltered? I think if you’re a middle-class white man, probably.

The positive reviews all shared similar tunes, so it is not worth looking at a number of them to see what different perspective that drew people in. I’ll evoke at this time Roger Ebert and to look at this film in the rosiest of lens than read his review:

Now you’re probably thinking, Faye, I’m starting to sense you don’t like this movie. I mean, your title has the word pretentious in it, that was my first clue. I’m also a keen observer and I’m sensing a little hostility in your language. As someone who loves this movie, I can’t help but feel you’re attacking ME personally.

There is this problem in criticism where we live in such a zero sum game world, nuance can very rarely exist. There are parts in Sideways I enjoyed, there are parts I laughed at. When Miles handed Maya his manuscript in a box, than handed her another one, I laughed deeply as a writer. Some of Miles’ sardonic human and dry wit was fun. Jack’s insistence of all alcohol tasting good as a juxtaposition to Miles in-depth criticism was both fun and meaningful for conveying these characters.

If most people want to declare this movie one of the hundred greatest movies made, fucking more power to them, I don’t care. It made 120 million dollars in box office, I’m clearly in the societal wrong here. But reviews should never, in my opinion, but about winning a fucking football game nor do points matter. Rotten tomatoes has Zootopia as a better comedy than Sideways, but Sideways just barely beating Guardian’s of the Galaxy 2. It doesn’t matter.

What matters to me is how media can evoke a response and the totality of that response outside of stars or numbers. How does it contribute, what do we take away from it, what does it add. And it is hard not to barrow the imagery of this movie when describing it, the metaphors of the alcohol tasting as comparison to your high level critics and general movie goers. So many reviews reflect that very imagery, often describing it in the same tones of Miles towards wine he likes or dislike — Quaffable, but not transcended.

Regardless, this movie did not work for me and that’s clear. What I offer from here on out is the ways in which it did not work for me. The ways it did not appeal to someone with my perspective. I think one of the greatest looks at criticizing criticism is found with my main man Dunkey:

Lets Get Into the Shit

I just rewatched this movie for the first time after about fifteen years. I wanted to give it a chance because I was in a place in my life where I could better relate to drowning in alcohol and sorrow. I could relate to finding and losing relationships, to love and loss and of the stuff in between. I could better relate to disappointment and failure and wondering what I should be doing with my life and if it would be better to give up. Depression and despair hit differently as an adult.

So, yeah, I thought I could relate to and understand this film better. I saw the positive reviews to help bias me towards a better disposition. What happened instead is I actually had a significantly worse experience, to the point I had to pause the movie, get up, and just vent to my roommate about how asinine the final scene was. I was actually swearing at my computer in disbelief.

I believe people fell in love with this movie based entirely on the impact of it’s hour mark scene. If you’re not familiar movies follow a formula in which the biggest impact of the movie happens near or around sixty minutes in. While I watched this movie, I wasn’t looking for this scene, I was trying to just take everything at face value. When I finished this movie, I suspected with great certainty the hour mark scene would be where Miles is talking wine with Maya and I was right. I think how you relate to this scene will ultimately make or break this movie for you.

“I don’t know. It’s a hard grape to grow. As you know. It’s thin-skinned, temperamental, ripens early. It’s not a survivor like Cabernet that can grow anywhere and thrive even when neglected. Pinot needs constant care and attention and in fact can only grow in specific little tucked-away corners of the world. And only the most patient and nurturing growers can do it really, can tap into Pinot’s most fragile, delicate qualities. Only when someone has taken the time to truly understand its potential can Pinot be coaxed into its fullest expression. And when that happens, its flavors are the most haunting and brilliant and subtle and thrilling and ancient on the planet.

While at the surface level this is poetry in motion. In writing circles we refer to this with a jerk-off hand gesture and call it waxing romantic, where writers just indulge in beautiful metaphoric imagery. It also to a point takes on the horoscope effect where it is vague enough most people could likely relate to this. They could feel this is true of themselves and if only for the love and appreciation of someone else, then they could truly shine.

The easier truth is must people need therapy and to learn better tools around communication and navigating their own emotions. They need to better tools to address these needs, while being emphatic towards other, and understanding boundaries. It is established Miles goes to therapy and has anti-depressants but it’s an entirely superficial plot element without real substance to it. If there was real substance, Miles would at time quote the therapeutic tools he learned to help minimize his behavior with drinking or crossing boundaries. We would gain value in seeing where these tools benefitted him and where his stress was too great to the point he disregarded them. It would’ve been a different and more complex layer giving more meaning to scenes than a cause (bad thing happens) effect (Miles is reckless/drinks).

It is clear that Miles effectively wants a women to save him or believes his salvation can only come from this. He thinks it somehow going to be his ex-wife and we establish this early with mom’s birthday dinner and his two year divorce being ever present in his mind. And this longing for women saving the male protagonist was clearly more pronounced in our zeitgeist in the 2000s, with Eternal Sunshine dealing with the exact same conceit if not more obviously and directly stated.

The reason the plot hits so much more repugnantly to me now is Incel Culture or the toxicity of the friendzone idea. This movie is 2 hours of shitting on women in the central ways you can do it. The first is deification like in the case of Miles and the second is Objectification like with Jack and if you want to truly understand these ideas then read the book Herland, written in 1915, by Charlotte Perkins Gilman, the same woman who wrote Yellow Wallpaper.

The movie was written by Payne and Jim Taylor, from the novel by Rex Pickett. One of its lovely qualities is that all four characters are necessary. The women are not plot conveniences, but elements in a complex romantic and even therapeutic process.

Roger Ebert suggests the women are not plot conveniences in this movie, but elements in a complex romantic and even therapeutic process. But whose process, Mr. Ebert? How are they not just props for the stories of these men? The women are in this movie purely for the benefit of the two male characters. The central plot of this movie is essentially Jack wanting to fuck someone and cheat on his wife before he gets married. And he does so with two different women, leaving one with lasting emotional damage to her and her daughter and betraying the trust of the person he marries. We’re suppose to believe he has come around and actually loves his wife and those rings are irreplaceable just like wife is and therefor he learned his lesson and we should forgive him! So long as men have suffering, they deserve forgiveness is the lesson of this movie. Seriously. And honestly I don’t know what they want me to take from the marriage scene depicted below.

Jack turns to Miles and grins with some knowing grin. Is it that he got away with cheating? Is it he is a new man and is happy to make the right decision? I have no reason to believe this isn’t suppose to be a happy scene. It is a happy scene for Jack for sure, but fuck the feelings and betrayal of his wife. And that emotional tear filled scene about the rings and being irreplaceable is completely hollow to the actions of this actor who is known to lie at all stages to get exactly what he wants. And maybe we see through this, maybe the audience sees through this, but fuck if I don’t believe many people look at this and think it’s good and it’s fine and it’s okay. Cheat on your wife before you get married, but feel really bad about it and it’s fine. And I hear things like, what a great character study, and I wonder why? There is absolutely nothing special about this story, about Jack, or about Miles. They’re are a dime dozen, I’ve known both men time and time again. But let’s look at this conceit with our main boy Miles.

You see, within the context of this movie Miles is simply…just misunderstood. That’s the whole point of his beautiful speech on wine that is clearly a self insert. He isn’t an awful person that covers for a predatory abuser, lies to women, steals money from his mother a day before her birthday, or a bad writer — he just hasn’t been appreciated enough for how great he truly is or how great he could become if only for the love of one good woman or the right publishing company. And all those bad things? Well, it’s okay, because he’s self loathing and that makes up for it all. So long as you feel bad enough about yourself, it doesn’t matter how shitty you are to other people. And honestly, if you want to see this character study done well, watch Bojack Horsemen. If you want to see alcoholism destroying your life to the point of suicidality with expectations not meeting reality as you slowly become less relevant and removed from everything you loved than watch the The Worlds End.

Roger Ebert

I can’t stress enough that I don’t care that Miles is suppose to be unlikable. I don’t need him to be likable, I don’t need his values to reflect mine, I don’t need some sterile story removed of sexism or some other non-sense like this. I also think Giamatti played the intended character perfectly. I love Always Sunny, which is five of the most awful people saying awful shit. However, what does the plot of this movie, what does the resolution of this movie, say about the characters and the values these characters have? A great video essay on how sexism is modeled and reinforced within movies and television shows is here, with a comprehensive breakdown of Big Bang Theory. And sexism is not simply thinking women are inferior, it is also the ways intentional or not that you dehumanize or objectify women.

Now, let’s get to Maya’s phone message at the end, before Miles’ does a Good Will Hunting and goes sees about a girl. At the surface doesn’t this scene just tie everything together so beautifully in the ultimate arc of redemption, where Miles is vindicated and seen and loved for who he actually is!? IS THIS THE RUG THAT TIES THE MOVIE TOGETHER!?

Well, one thing I can say is it’s pretty convenient.

The Fractal Story

A fractal is a mathematical concept in which items share the same relative dimensions. Imagine if you will a house and inside that house is an exact model of that home. But this is an exact model, meaning it includes a tiny model inside of it ad infinitum

The movie Sideways is a script, written about a book, which is about an author trying to publish a book that is semi-autobiographical. The book inside of this story is spoken about as being hard to publish, because publishers look at quantity and marketability over content and meaning. Every time we’re talking about Miles, every time we’re talking about Miles’ book, we’re talking about the actual author and the actual movie we’re watching. The wine criticism is direct parallels to general criticism of novels and movies, given film critics a relatable hero.

When we compare Miles to the book he writes, we get the complexity of his character. He doesn’t really understand his life and describe it as
“moving into a kind of a Robbe-Grillet mystery — you know, with no real resolution.” This is the fractal pretentious bullshit I’m talking about.

He vaguely intends to kill himself, that’s the mystery, which is communicated both in his speech to Jack about how he has to be published before he can do so and Maya’s asking him if the father in the book committed suicide as a framing device to the other lingering question the movie has yet to answer: is Miles the 1961 Cheval Blanc? Is the wine that he held on to for hope of something better. Has he peaked and from here will he only get worse and worse? Or is there hope yet?

When I originally watched the scene of him drinking the wine inside of this fast food dinner I envisioned him doing so to make his own destiny. That he made a special moment instead of waiting for something special. Watching it again, I think the logic of the story and the script is intended to make us think he has given up. After all this scene happens after he finds the former love of his life pregnant and therefor forever out of reach. Every time something bad happens to him he breaks down, runs away, turns to alcohol and the following scene has him embracing the Cheval Blanc. He has peaked and now waits only for death. One could also think he is drinking it now, because he knows he’ll never be back with his wife and that’s what he was really longing for the entire time. I think there are a few ways to understand this scene, but ultimately I prefer and will walk away with my initial understanding. This understanding is I believe a point of kindness I’m not sure Miles deserve, because it comes from a place of self-empowerment that Miles refuses to embrace throughout this entire movie. (Yeah, he does shower and tries to honestly pursue Maya, but that’s just shifting his infatuation from his ex to her. And honestly a lot of the times he doesn’t shower, wakes up after drinking, and just puts on new cloths before going on. He probably reeks in that double date.)

Originally the novel has the story ending at the wedding, where Maya comes to say she’s read his novel and through reading it loves him. I see so many men with this one-sided fantasy. Where they put in this work, write this story, put all of themselves out there and that by doing this they can hook women. It is a mentality that you have to “earn” women, rather than really pursuing meaningful relationships, conversations, or anything else of real substance. They don’t want a relationship, they want a mom or therapist or they want to capture love as an earned prize of validation.

And the reason I paused the movie, the reason I got up to vent, was Maya’s speech was so fucking indulgent to this mentality — the misunderstood man.

I think it’s really lovely, Miles. You’re so good with words. Who cares if it’s not getting published? There are so many beautiful and painful things about it. Did you really go through all that? It must have been awfully hard.

This speech must have felt so vindicating to so many people as beautiful. Finally, the this lost sole found someone who could see all that beauty. Who has the patience and care to make “flavors that are the most haunting and brilliant and subtle and thrilling and ancient on the planet.” Fucking shit.

Let’s take this for a moment from Maya’s perspective. He lied about being published and covered for his friends cheating without intention of telling her. He accidently slips, then comes clean, because as a manipulation tactic it is a way to gain trust. “Hey I could have lied more, but I didn’t, so see how honest I am”. She tells him off by saying she ended her last relationship because her husband was a liar and a fraud.

This woman would not get a letter from this man and think it is cute and romantic and worth reading. It would be sad and stalker vibes, ‘oh right, he knows where I live’. This is not a woman who would than read 1000 words of his shitty novel to try to really understand him. This not a woman who should forgive him and see he’s actually really beautiful. This vindication is false, shitty, and from the perspective of a male author writing a wish fulfilling fantasy. It is absolutely cringe.

Could all of this happen? Yeah, absolutely it is all possible, I’m not saying it isn’t. In this regard I’m not going to say it isn’t unrealistic either. What I am saying is regardless of all that this is at its root a male wish fulfillment fantasy that asks men be forgiven of everything and loved so long as they’ve suffered appropriate amounts. And I see people unconsciously taking these values away from the movie, where what does cheating or lying matter when a man “feels” love deep down inside. “Oh baby, I’m sorry I cheated, but you know I love you.” This is honestly the messaging and it is awful.

Miles serves as a good representation of the misunderstood nice guy. His story is about finding someone who can actually see him. All of his bad behavior is fine because he hates himself more than anyone else. These are values that circle through our culture and are reinforced in this movie and I hate it. I absolutely hate it. It isn’t directly Incel material, but imagine this movie ending without Miles getting a call from Maya. Where does his character go then? Is it suicide? Is it bitter loneliness? Does he start harassing his former wife with drunk calls down the line until a restraining order is filed? He, himself, is not redeemed through his own actions, realization, or character growth. He is not getting better through himself, his life, or anything else except for the love of Maya. Tell me again how she isn’t a plot device that is there to fix his life.

When looking at a potential sequel to this book the author wrote out the character of Stephanie. He did it because actress who played her, Sandra Oh, had become the ex-wife of the director Alexander Payne. He wanted to make sure Alex wasn’t uncomfortable if a sequel was made. She was written out because she may have made on of the men uncomfortable. In a vacuum this isn’t unreasonable, but lets not look at it within a vacuum, let’s look at it by the script, the characters, and the movies and how women are used in them.

One negative review said this movie perfectly captures two kinds of male menopause and I don’t disagree with that. It suppose to capture human experiences and that’s what positive reviews talk about. How human this movie is and I honestly don’t see it. This movie may have hit closer to home for the 30-year-olds of 2004. It may still hit home for the middle class white men of today who confuse their experience as the default human experience. It isn’t entirely a bad movie, it isn’t like it fails at every level by any means as I express way earlier in this essay. There are parts I like, there are parts that I think work, and parts I fucking hate.

For my money if you want the same relative experience without the bourgeoise bullshit and pretentiousness, than watch City Slickers. I honestly think it’s everything this movie was doing but better. And one could argue for the performance, the music, or the director’s/actor’s lineage of films but that’s where movie critics go — that’s their culture. As a writer, I look at the story and what the story conveys and what we can take from it.



Faye Seidler

I write essays on literature, pop culture, video games, and reality. A throughline of my work is metanarrative horror and defining what it is to be human.