Overall Impression – Hilarious, smart and moving.  SEE IT!


Who’s your main character? – Miles.

What’s he trying to accomplish? – Professional: enjoy a fun weekend in wine country with his best (and soon to be hitched) friend Jack.  Personal: get over his divorce. Private: find true love again.

Who’s trying to stop him? – Miles is definitely his own worst enemy, but Jack contributes his share of obstacles, too.

What happens if he fails? – Miles will remain miserable and alone.


Orphan – Miles’ divorce (2 years prior) has left him insecure and cynical about finding another woman.  His best friend Jack is also about to be married, so in a sense Miles is being left behind.

Wanderer – The guys travel to wine country, where Miles attempts to teach Jack the intricacies of wine tasting.  Jack also learns about Miles’ interest in a local waitress named Maya… and the extent of Miles’ insecurity around women. So, Jack takes it upon himself to get his best buddy laid.  The perfect plan, given that he also wants to sleep with Maya’s friend Stephanie before he gets married.

Warrior – As Jack befriends Stephanie, Miles works on opening up to Maya and putting his divorce behind him.  Jack and Miles also talk more candidly, each confronting the other about their respective problems.  Miles also pursues a book deal more aggressively.

Martyr – There are a few martyr elements.  The funniest is when Miles sneaks into the house of a random waitress that Jack slept with, in order to retrieve Jack’s wallet which holds his wedding rings.  However, Miles’ bravest moment comes at the end, when he finally puts himself out there and goes back for Maya.


There aren’t many movies I can watch over and over, but SIDEWAYS is one of them.  It’s gotta be up there with LOST IN TRANSLATION, another great dual-character study that’s just so… likable.

The thing is, whenever somebody told me about the movie before I’d seen it, it just sounded boring.  I got various versions of “Well… it’s about these two guys who go to wine country, they meet a waitress… and yeah, it’s hilarious.”

Well, it was hilarious, and much more.  The great thing is, you don’t even have to like wine to enjoy SIDEWAYS.

Oh, if I haven’t said it already… SEE IT!  SEE IT!  SEE IT!

– Dan Pilditch

3 Responses to “SIDEWAYS”

  1. Nick May 9, 2009 at 9:22 am #

    I LOVE this movie! Thanks, Dan, for the great analysis!

    A few questions you’ve got me pondering – Considering the title of the movie, why do you think Miles is moving sideways through life? Maybe Miles divorce is a symptom of a greater problem? If so, do you think it’s addressed in the film? Also, could it be that Miles knows he’s moving sideways and is the true source of his depression? I wonder what was the cause of his divorce? 🙂

    “I’m not drinking any…merlot!” 🙂

    Hey – I wonder why Miles is adverse to Merlot? Does he see himself “stuck” in life as a “common Merlot” and not something more “grand?” 🙂

  2. danpilditch May 14, 2009 at 5:05 pm #

    Hey Nick,

    good questions, and i agree with most of your thoughts.

    I’m not sure if Miles’ divorce is a symptom so much as the cause of his problems, and these are the problems that are addressed in the movie.

    I’d say these problems give him plenty of reasons to feel depressed: he’s failing life professionally (the book deal), personally (he’s lonely), he’s a loser compared to Jack, and he’s still hung up over his ex-wife.

    In other words, he’s moving ‘sideways’ through life instead of forwards, all because of his divorce.



  3. danpilditch May 14, 2009 at 5:11 pm #

    And as for the Merlot…

    I’m pretty ignorant when it comes to wine, but there’s a scene between Miles and Maya where he explains why a certain wine is his favorite – because he sees those specific grapes as fighters, because they’re so delicate.

    If Merlot grapes are easier to grow, i’d say Miles’ dislike of that type of wine stems from his lack of respect for the grapes. In other words, if the grapes aren’t fighters, why should he respect the wine?

    (I saw the delicate grapes that make Miles’ favorite wines as metaphors for himself, while the more robust grapes that have it easy are metaphors for Jack.)

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