Sideways appeared on my radar in an unusual manner. It normally wouldn’t be the type of film that would necessary spark my interest, especially when it was released back in 2004. I could have deprived myself of what is a beautiful and very funny film all because I am not a wine drinker.

So how and why did I end up watching Sideways? It was thanks to a podcast and a comedy festival I went to a month ago! Peter Helliar hosts a podcast called ‘You Ain’t Seen Nothin’ Yet’ where he talks to other comedians and friends about a well-known film they haven’t gotten around to seeing yet.

If I also haven’t seen the film the episode is about, I like to watch it first in preparation before listening. So when it was announced that the film for the live episode recording I was going to at the Grapes of Mirth festival was Sideways, I had planned to watch it in time for the recording. Unfortunately that didn’t happen (apparently you get quite tired doing a 10 hour drive) but I did watch the film the night after the recording. Luckily for me, most of the audience hadn’t seen the film either, so Pete did try to steer away from too many spoilers.

I highly recommend checking out the podcast, as there are some great insights to the film. For me, it really enhanced my viewing experience.

When it came time to capture my thoughts on the film, I didn’t want to do so that night. Partly because I didn’t have the time as I was driving back home the next day but mostly because I wanted time to develop my own thoughts on the film. I’ve now had the time to process and just watched the film for a second time to take stock of what connected for me. There are still things that I agree with that were spoken about in the podcast, which I will call out when making reference to in this review.

Second time around, I really enjoyed the film just as much as the first time and can easily see watching it multiple times in years to come.

Sideways follows the story of Miles and Jack, two middle aged men who are spending a week visiting vineyards across California before Jack’s wedding on the weekend. Miles has arranged this week getaway for the two friends, to share his vast knowledge of wine, hang out, and play golf together. Yet both are battling their own form of an existential crisis which adds friction between the two on the trip.

Jack is an once popular TV star turned voiceover actor and as the week progresses, is having a dramatic case of cold feet. Does he really want to get married? He sees this week as his last week of freedom and wants to use it as a chance to cut loose and party. Aka sleep with other women.

To me, I don’t think it is crystal clear when Jack makes this decision. It was obvious that he was very keen to start this trip and whether that started off as just wanting to get some air to think if getting married was the right move or if he have a very clear goal from the get go, I’m not sure about. The way things escalate, I would suggest there is no plan as Jack reacts rather impulsively.

I find the character of Jack insufferable, difficult to empathize with, and a lot of the time pretty cringey. Kudos to Thomas Haden Church on the way in which he plays the role. For anyone else of my vintage you may also remember him from his role of Lyle in George of the Jungle, another insufferable type character!

Miles on the other hand, has been divorced for two years and has yet to start another relationship. Despite the fact his marriage was an unhappy relationship and that his ex-wife has moved on, he is stuck in the belief that they may get back together some day. He works as an English teacher, has written his own novel, and is waiting on news if it will be published. Of the two men, I think Miles is the one with the more redeemable qualities and who I found myself relating to on a few levels.

Enter Maya and Stephanie, the two women which Miles and Jack spend most of the week days with. Miles already knows Maya as a waitress where he frequently dines when on wine tastings and Stephanie becomes the subject of Jack’s lust. The (un)published novel is something that Jack uses as the excuse to tell the women he is attempting to woo for the reason of their trip. You know, because mentioning he is getting married on the weekend would be awkward.

Maya is a fellow wine connoisseur with a sharp palate, the perfect pairing for Miles. She is intelligent, measured, and provides a lot of light to Miles’ shade. Her character has some beautiful ways of talking about wine and life. They also share a similar experience in their marriage breakdowns. Virginia Madsen brings to life the character of Maya, giving her some complexities and a real part of the film.

Stephanie on the other hand, while also having a good knowledge of wine, is quite impulsive. After meeting a man for 24 hours, she is having conversations about moving in with him and introducing him to her child. Don’t get me wrong, I am not saying that Jack is innocent in anyway, it just seems to come across as moving very fast. While they share this attribute, unlike Miles and Maya where their commonalities compliment each other, the similar behaviour of Jack and Stephanie works against them.

The scene were the four go out to dinner together for the first time, really shows the differences between Jack and Stephanie vs Miles and Maya, as well as between the two women and two men, just from the types of conversations we see them having.

It’s probably the reason why I have connected with the film, I do adore this type of story telling. There is so much that you could unpack from each of the characters and their relationships with each other.

Having good material is one place to start, having the strong cast to bring it to life is the other part of the equation. Paul Giamatti’s performance is what really makes this film for me. His facial expressions alone add so much to each scene, really conveying the way in which Miles is thinking and feeling. It’s a strong cast however without Giamatti, the film wouldn’t be what it is.

Apart from the quality of the story, the film also has a great quality in how it has been filmed and the way in which it flows.

One of the things that was mentioned in the podcast I attended was about the level of detail in each shot. It was said that everything is included in the film for a reason and I really agreed with this comment. One such example is when Miles and Jack stop at Miles’ mother’s house on their way across California.

Miles says they are just stopping in to wish her a happy birthday. Yet when they get in the house and are asked if they are staying for something to eat, Miles says yes. Jack gives him a look of ‘what do you mean, we should get going’ where Miles’ response is “just a snack”. Cue the next scene which shows the three of them sitting at a table, much later in the evening, with a fully cooked meal on the table. That is just one small example that the whole film is filled with.