This film is the elephant in the room for me. I might as well come out and say it.

I’m not a fan of Sideways. Yes, I know. This is a site dedicated to Virginia Madsen, and yet here I am, admitting I don’t love the film that resurrected her career. The film that brought her back into Hollywood’s spotlight, earned her numerous accolades, and showered her in awards.

How can that be?

It’s not for lack of trying, I promise. Before rewatching, I half-convinced myself that maybe it was a matter of timing. I was younger when I first watched it, and I thought perhaps a more world-weary, mature version of me might appreciate it. So I gave it another go.

And. Nope. I’m sorry, but I still don’t get it.
At its core, Sideways is a road movie – We follow Miles (Paul Giamatti) and Jack (Thomas Haden Church) as they embark on a trip through California’s wine country, celebrating Jack’s upcoming marriage. But the two friends have wildly different ideas of what this last hurrah should be. Jack wants one last fling before settling down, while Miles, reeling from his recent divorce, is searching for something deeper, using his love of wine as the backbone for the journey.

Along the way, they meet two women—Stephanie (Sandra Oh), a free-spirited firecracker, and Maya (our very own Virginia Madsen), a thoughtful and introspective waitress. The women reflect the two men perfectly: Stephanie with her spontaneity mirrors Jack, while Maya, with her quiet contemplation, is the ideal match for Miles. It seems like the perfect set-up, right?

But of course, things go awry, and Jack’s recklessness threatens to ruin everything, including the connection forming between Miles and Maya.

So, why don’t I like it? I don’t know, really.

The older, more “mature” me thought I’d appreciate its subtleties this time around, but instead, I found it boring.

Maybe I was too young the first time and now too old the second? I see a lot of myself in Miles and know plenty of friends who could be Jack, but still, the film leaves me cold and wanting.

Maybe it’s because I’m a beer man over wine? Would it have been different if they’d been drinking beer all the way? Who knows?

That said – Virginia Madsen as Maya? You can’t help but appreciate that, I mean, c’mon.
Virginia Madsen deserved every award she got for this performance. Even as someone who doesn’t drink much wine, I hung on every word of that speech about wine’s evolution. It’s a moment that transcends the film, one that you can’t imagine anyone else pulling off. And I’m not just saying that as a fan.

Looking back, you can see how her previous roles from The Rainmaker to Sideways; The Florentine, Almost Salinas, Just Ask My Children and American Gun they all built to this one. Those performances laid the groundwork for Virginia Madsen to totally transform into  Maya, and Sideways was her moment to truly shine.

If you watch the speech again, separate from the context of the film she is almost telling you this herself;

Would I recommend Sideways as a whole?

Honestly, no. As a film, it doesn’t resonate with me. But as a showcase for what Virginia Madsen is capable of? Absolutely. Her performance, to me,  is the jewel in Sideways’ crown, and for that alone, it deserves a watch.

Availability:

Easy to find on DVD, and it’s on plenty of streaming services. You’ll pay over the odds for a copy on Blu-Ray though – Not sure why.

Gallery:

Trailer:

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