Sideways (2004)

Published: Mar 18, 2009 |Updated: Sep 10, 2023


Two guys in the prime of their life; Miles, an unpublished author, schoolteacher, wine conoisseur, divorcée, and self-proclaimed loser; and Jack, a has-been TV-star, to-be husband, and desperate horndog; are going away for the week, in search of wine, women – and themselves. Sideways is a story about the healing power of authentic, male friendship and a prudent challenge to take a chance on life. Come, let’s drink with Jack and Miles!

Genre Comedy
Production year 2004
Director Alexander Payne
Male actors Paul Giamatti, Thomas Haden Church

A study in the value of good buddies

As the movie opens, Miles is running late for his rendezvous with Jack. The two middle-aged men are both cooking in the broth of their own midlife crisises; Miles is struggling to get his semi-autobiographical novel published and is caught on the golden leach of memories from the now-dead marriage with Victoria, while Jack is reluctant to tape himself to the oaths of his imminent marriage, and goes away with Miles on what to him is his life’s last hunt for ass. It’s a nice setup for a different roadmovie, a roadmovie with heart.

Miles is not a structured man; the film wants us to know this straight away. Miles, we can tell, has a way of running late for things. And even after he shrieks at the microwave clock, he continues at his docile pace, knowing full well that he can blame the traffic when he arrives at the Erganians’ (the parents of Jack’s fiancée). Note that the way he continues his morning ritual in no way reflects his being late.

We are already being told that there is a vast distance between Miles’ understanding of what he must do (hurry up) and what he will do (have a nice, cozy morning – just like usual). I’m emphasizing this early scene because it communicates all the reasons why Miles is not having the success he wants with his book and why he feels depressed. Quite simply, Miles is out of integrity with himself.

Not only is he out of integrity with himself, he’s also a bit of a Mama’s Boy. Miles takes the unwilling Jack on a detour to his mom’s to mark her birthday, and we see the size of Miles’s libido shrink to the size of a nucleus in Phyllis’s presence. Unable to handle her with any degree of clarity, he is trapped in her personality, at the mercy of her whims and desires. The soft and friendly Miles, in an unbefitting move, steals several hundred dollars from her dresser drawer; proof positive of his feelings of entrapment; only his embitterment could cause him to think that stealing money from this sweet and elderly, if neurotic, woman is fair game.

“You gotta get laid, Miles”

Jack and Miles finally hit the road headed for wine country, and Jack makes it very clear – he’s going away to have fun. “Miles, you have been officially depressed for like two years now!”. Whereas Miles is the docile, cuddly carebear, Jack is more of the direct, testosterone-laden coyote. Jack has more juice, more zest for life than his depressed Xanax-munching friend, and he pushes Miles to step it up.

«You gotta get laid, Miles», Jack exclaims over the lunch table. «You used to be a negative guy – even back in college. But now it’s worse! You’re wasting away Miles, teaching English to fucking eight graders, when they should be reading the books that you wrote!» Jack is giving Miles the gift of challenge. He pushes him, like a good buddy should, to step it up – become better. It’s a beautiful thing really, despite its apparent crassness. It also points to a recurring theme throughout the movie – Jack keeps telling the people they meet that Miles is a published author.

This well-meaning white lie is meant to push Miles to reach for his goal, but it’s not working too well. There is no true challenge in a lie, and Miles can piggyback off of the lack of integrity in Jack’s recurring storytelling to escape further from his responsibility to take charge of his own destiny.

Jack is a pragmatist, confused in his own entirely unique ways. He doesn’t have the refined tastes of Miles, but he knows what he likes and is prepared to reach for it. And now, he wants to get laid. Jack, in his infinite wisdom, has hatched the brilliant idea that the best way to prepare himself for a life of monogamy is to dip his dick down the honey pot as many times as possible. But, so goes the story, with the honey comes the bees…

The true (anti)hero of Sideways is Miles though – and he is one strange man. Despite his total limpness in life – pass him a glass of fine wine, as long as it’s no Merlot (“I won’t drink no fucking Merlot!!!”) – and he comes alive like a flower bud at the first sight of the morning sun. He becomes a poet, and weaves colourful tapestries with his words to describe the sumptuous and subtle marvels experienced by his finely tuned palate.

Miles is not a mere wine-lover, he is a conoisseur. And when it comes to things concerning taste, he has discernment – notice how he is always clear and directed when it comes to matters of his palate, be it about spinach croissants, wedding cakes, or fine wines. I find this an interesting feature of his personality – his masculinity is in his tongue. As I said, he is a strange man!

Why wine is so fucking good

What are two wine-drinking guys without two wine-drinking gals? Not much, especially when they both need to get laid. Cue Stephanie and Maya. Maya is the blonde, sophisticated gal who works at The Hitching Post, the hangout spot for Miles when he drops by Solvang, California. Which, by the looks of it, is quite often (Miles loves wine, remember!). Stephanie is Maya’s friend – and Jack’s target.

Much to Miles’s surprise, it turns out that Maya quite likes him. He is oblivious to it; Jack has to point it out to him. It seems that Miles’ palate has taken most of his sensory capacity.

One thing leads to another, and Jack gets Stephanie to polish his rocket, to wax his monkey, to – ah, you get the idea. He doesn’t even think about going for Maya; he is a cool, solid guy after all. And as Maya and Miles get further acquainted, the plot leads up to what is one of my most favourite dialogues in a movie ever. It’s the famous discussing-our-love-for-wine-on-the-porch-while-our-friends-are-shagging-next-door dialogue (TM). Maya breaks the question to Miles, as if she has wondered for quite some time.

Why are you so into Pinot, Miles?

“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, which can grow anywhere and thrive even when neglected. No, Pinot needs constant care and attention… And you know, in fact it can only grow in these really specific little tucked away corners of the world…. And only the most patient and nurturing of growers can do it, really…. Only somebody who really takes the time to really understand Pinot’s potential can then coax it into its fullest expression… And then, oh… it’s flavours are just the most haunting and brilliant and thrilling and subtle and ancient on the planet…”

Way to go with the words! You will of course realize that the Pinot grape is a metaphor for Miles. He is describing Pinot, but is really talking about himself. He is talking about the vast potential that he knows he has inside, but that he just can’t manifest in the world. And as it so happens, he needs someone to nurture it out of him.

He needs to be loved. Because he is unable to love and believe in himself. It’s a very soulful moment, and describes well Miles’s immature relationship with mother energy: The wine grower is his mother. And whichever woman is to be with him, will be his mother. Victoria didn’t like that, so she left him. And Maya would probably too, if they got together. Yet, the soulful, heart-openness of the moment creates a bridge between them, and Maya continues with the intoxicating poetry:

What about you, Maya? Why are you into Wine?

…I like to think about the life of wine, how it’s a living thing. I like to think about what was going on the year the grapes were growing, how the sun was shining, if it rained…what the weather was like. I think about all those people who tended and picked the grapes, and if it’s an old wine, how many of them must be dead by now. I love how wine continues to evolve, how every time I open a bottle it’s going to taste different than if I had opened it on any other day. Because a bottle of wine is actually alive—it’s constantly evolving and gaining complexity. That is, until it peaks—like your ’61—and begins its steady, inevitable decline. And it tastes so…fucking…good.

Totally…sexy. Miles is completely choked up, desiring this woman with his very soul. But he is too afraid. He doesn’t capitalize on the moment, even though the invitation was served on a silver platter. Maya is very disappointed. Miles just hates himself.

The plot ripens

And this is when the brotherhood really starts kicking in and showing the value of a good buddy. There is a scene on the golf course where a jerk hits into them, and Jack and Miles both fly off into a fun-filled display of anger. I really wish I were there with them every time I see this scene. First of all, I’m not too good at expressing anger myself; I’m generally cool-headed, yet I love the energy in this scene. For Miles, clearly, it’s very healing to connect to his balls and faceoff with this fat-assed hillbilly buffoon. Because shortly after, Maya opens her honeypot and Miles is a happy guy.

Then, a little slip of Miles’s tongue and everything blows up. After all, Jack has been balling Stephanie all week – telling her tales of their rosy future together, yet he is getting married on Saturday. He gets a good, and rather well deserved beating when the truth comes out.

You would think this is the wake-up call Jack needs, but not until he finds himself running naked through town, escaping the infuriated husband of the waitress at the local diner – another fling he decided to chase on the rebound from Stephanie – does he break down in tears with the realization of what he is doing. Jack realizes some deep truths about his own irresponsibility and immaturity, and faced with his fear, his mind shifts. He is ready to marry.

Miles on the other hand learns from his agent that his book has been rejected by his only lead at Conundrum, and throws a fit of rage in a vineyard, when they won’t serve him the wine he needs to numb the hurt. He blows a fuse and pours a barrel of wine on his head, before he is lead out of the room by Jack, steaming. Again, Miles is connecting to his balls. What seems like actions of a nutter are actually deeply therapeutic. Fuck convention, let’s smash wine barrels on our heads in public!

Rounding off the bottle…

«I’m a smudge of excrement on a tissue, surging out to sea with a ton of raw sewage.» Welcome to Miles’s view of himself. He is not exactly the epitome of someone who loves and respects himself. And as we understand, it’s because he has not found his purpose; he has not found that deep, authentic core that makes him burn with the flame of passion.

But the show must go on, and in the end Jack gets married, and Miles’s life continues. He’s not happy with it, not happy with himself, yet I feel there’s profound beauty in the ending. It makes me think of all the people in the world who go through life, trying their best to make it work, their best to better themselves. But in the end, most of us tend to give up a little, settling for less than what we know deep inside is our birthright. And in silent moments, with only our broken selves as companions, we think of what could have been.

Sideways is a deeply human movie. It’s very refreshing in this day and age to see a story totally free of cynicism, a tale told with deep compassion and respect. Everything about it just exudes this warm, embracing quality that makes me happy to be alive. Sideways is not a movie that challenges us as much as it is a movie that helps us embrace the less than perfect parts of ourselves. So many guys constantly beat up on themselves, finding this somehow an expression of masculinity. It leads nowhere.

Enjoy Sideways. Savour it, work it around your mouth, tease your palate. And pour it into the parts of yourself that are broken, and learn to embrace them with love, so that you can move on with your life and think of not what could have been, but what will be.

A confession – there’s a lot of Miles in me. I’m okay with that.

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