Theatrical release poster for 'Sideways' (2004) (AMP Awards/Wikipedia)

Theatrical release poster for ‘Sideways’ (2004) (AMP Awards/Wikipedia)

Way back in early 2005, one of the first movies I saw at the cinema that year was the American comedy-drama Sideways, adapted from the novel by Rex Pickett.

Sideways is about two friends in their early 40s, Miles (Paul Giamatti) and Jack (Thomas Haden Church), who spend a week holidaying in California’s Santa Barbara County Wine Country before Jack’s upcoming wedding. Miles is a depressed divorcee and frustrated writer who is anxiously hoping that a novel will soon be accepted for publication, while Jack is a fun-loving free-spirit but also a senseless womaniser who is keen for a last week of action before he weds. Very quickly, what Miles had hoped would be a quietly pleasant week of golfing, wine-tasting and dining becomes complicated and exciting – but ultimately disastrous – after he and Jack become involved respectively with locals Maya (Virginia Madsen) and Stephanie (Sandra Oh).

At the time, I enjoyed Sideways a lot – I found it very funny, but also bittersweet and moving.

A year or so later, I also read and enjoyed the novel (and in more recent years I have also read and enjoyed the two sequels).

Eventually when Sideways became cheaply available on DVD, I bought a copy and as years passed I watched it a few more times.

A few years ago, however, I suddenly became hooked – and since then, I’ve lost count of how many more times I’ve seen Sideways. At one point for weeks on end, I was watching it late every Friday night.

As well, last year I bought a copy of Rolfe Kent’s soundtrack album (and it is playing in the background as I type this).

Why did I become so hooked on this film?


Like many good things in life, Sideways is straight-forward yet very effective in what it does. It’s a low-key yet well-crafted film that every time I watch it still makes me smile and groan and laugh and feel a little sad.

A few years ago, I began re-appreciating Sideways so much that it became a comfort film. The reason why I used to watch it late Friday night for weeks on end was that it was a good way to start unwinding after a working week and see in the weekend.

As well, because I had changed since I first saw Sideways in early 2005, it came to mean more to me for several reasons.


One of those reasons had its preview during that very first time I saw it.

Early in Sideways, there’s a scene where Miles and Jack are walking from their hotel in Buellton to the restaurant The Hitching Post II for dinner, and Jack is telling Miles about his concerns regarding his upcoming marriage and life after that.

When I first watched that scene way back in early 2005, I marveled at Miles and Jack’s situation of (a) beginning a week’s holiday, (b) staying in a hotel and (c) going to a restaurant for dinner. At the time, I had done plenty of (a) (albeit mostly staying with relatives) but very little of (b) and (c).

A few years ago, however, my life had changed a lot – working away from home for a couple in months in 2009 had made me a huge fan of staying in hotels (and aspiring to one day perhaps living in a hotel); and since early 2007 I have eaten out most nights.

Thus, rediscovering Sideways reinforced some things I’d very much come to enjoy doing and living.

As well, there’s an amusing sequence that takes place after Miles’s plan to go golfing with Jack is thwarted by Jack instead spending the day with Stephanie. Thus, Miles finds himself spending most of the day doing things by himself – and although it highlights Jack’s selfishness and is accompanied by the soundtrack piece ‘Lonely Day’, to me it looks like a great way to spend a day.

Sideways hasn’t encouraged me to take up drinking wine, but it did make Santa Barbara County Wine Country look like a very nice place to visit. The prospects of me ever going there are remote…but who knows?


Another reason why Sideways came to mean more to me a few years ago was that by then I was in a similar situation to Miles and Jack.

When I first saw Sideways in early 2005, I was 33 years old.

A few years ago, like Miles and Jack I was in my early 40s.

As well, like Miles and Jack I was going through my mid-life crisis. Although mine was nowhere near as drastic as theirs, it weighed upon my mind at times – so ever since, whenever I watch them talking about what they’re going through I can relate to it much more.


Another reason why I have come to re-appreciate Sideways is Miles, because there are a couple of things that we share.

One thing is writing. Miles is a frustrated writer, whereas I was a would-be (or perhaps a never-was) writer. To cut a very long story short, for about 30 years I had thought that perhaps one day I might become a published author, but by 2010 I had very much killed that idea. Not having become a published author by now (and most likely ever) is one of my biggest regrets in life, although I must admit that finally killing that idea did take a load off of my mind – and as an alternative, I have very much enjoyed blogging here.

The other thing that Miles and I share, most of all, is depression.

When I first saw Sideways back in early 2005, I hadn’t yet been diagnosed with my depression – but I could relate a lot to Miles. We both had downbeat views on life, and dwelt too much on the past (and especially its failures).

After mid-2007, when I began my therapy and medication, I could relate to Miles a lot more.

There’s an especially powerful sequence in Sideways that begins with Maya attempting an emotional connection with Miles through their mutual love for wine. It’s a highly-charged moment – but unfortunately Miles (who suffers from anxiety and depression) finds it overwhelming and makes an awkward exit to the bathroom, where he snarlingly curses himself (“You’re such a fucking loser. You make me so fucking sick.”)

When I rediscovered that sequence a few years ago, it hit me hard and it has stayed with me ever since – and sometimes during the past few years, I have been unable to re-watch it. I have had many similar bathroom moments.


As I mentioned earlier, I find Sideways funny and pleasant yet also bittersweet and moving.

As its last third begins, the first major disaster takes place and the holiday quickly goes from one awful situation to another (although some of them still have their very funny moments). Even the journey home ends badly, and then there’s Jack’s bittersweet wedding…but at the end, there’s a last poignant sequence with some hope at last for Miles.



So far this year, I’ve only watched Sideways once or twice…but writing this, and listening to the soundtrack a couple of times while doing so, has got me thinking about revisiting it again in the near future.

There will be other comfort films to discover (or rediscover), but for several reasons Sideways will always remain a favourite.

Until next time, stay well and take care 🙂

About blackandblueman

Black and Blue Man lives in Sydney, New South Wales, Australia
This entry was posted in Happiness, Having a Laugh, Inspiration, Pain, Something to Think About, Travel. Bookmark the permalink.

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