Flawed Characters — Looking At Life Sideways!

Flawed Characters — Looking at life Sideways!

I love flawed characters.  Perhaps it’s because they seem so much more real. Join me for a little analysis of the screenplay Sideways, which is wonderfully written. 🙂

Logline: Two old friends setting off on a wine-tasting road trip…only to veer dizzily sideways into a wry, comedic exploration of the crazy vicissitudes of love and friendship, the damnable persistence of loneliness and dreams and the enduring war between Pinot and Cabernet. (Fox Searchlight Pictures)
Failure is a part of the human condition, and whenever we see a character in a screenplay that reveals this aspect of humanity, we are somehow reassured.  In the screenplay Sideways, the protagonist has been hard-hit by the failure of his marriage and the rejection of his novel.  Through the use of good character development, well-written dialogue and conflict, the authors take the audience/reader on a metaphoric journey filled with universal appeal while covering complex life questions, such as:  depression, mid-life crisis, honesty and infidelity.
The opening scene in Sideways reveals a lot about MILES RAYMOND’S character.  Miles is hung-over, and running late for an appointment that he had forgotten about.  The opening line says it all:  “…the fuck….” A worker [painter] is standing at the door asking him to move his car.  Dressed in only underwear, a bathrobe and a pair of clogs, Miles proceeds to move his car, and ends up falling asleep in it.  It is clear that he is somewhat out of sorts as he races back into his apartment in frenzy and shouts out the repeated one-liner, “Fuck!”  He is late for an appointment.
Miles is an eighth grade English teacher and a want-to-be novelist who has not moved on after going through a divorce.  He is a loser.  In fact, he seems to be going through the motions of life passionless, with the exception of his love for wine and his fascination with Pinot.  When asked about his love for Pinot his response is not only informative about the nature of the wine, it somewhat mirrors him.  Note the following excerpt:
                        Can I ask you a personal question?
                            (Bracing himself)
            Why are you so into Pinot? It’s like a thing with you.
Miles laughs at first, then smiles wistfully at the question.
He searches for the answer in his glass and begins slowly.
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 that can grow
anywhere and thrive even when neglected. Pinot needs constant care and
Weaving in Metaphor:
Is this explanation a metaphor that describes him? Is he admitting to his inability to weather the storms of life and his need for constant attention and affirmation?  He has not survived his divorce well, and exhibits the signs of someone who is not just down on his luck in life, but most likely depressed.  This middle-age man has been rejected in love and in his career as a writer.
In the middle of their vineyard adventures, Miles and Jack sit on the hood of Miles 12-year-old Saab sharing a bottle of wine.  Jack encourages Miles to simply write another book.  “Another” is the operative word, because Jack does not know that Miles book has been rejected.  In this moment, Miles’ loser mindset and lack of self-esteem is exposed to the audience/reader with his response to Jack.  Miles not only has no new writing ideas, he believes that he is washed up.  In fact, he tells Jack that he is not a writer!  “No, I’m finished.  I’m not a writer. I’m going to spend the rest of my life grading essays and reading the works of others…the world doesn’t give a shit about what I have to say. I’m unnecessary (a dark laugh). I’m so insignificant, I can’t even kill myself.”
Not only is Miles on a journey of self-discovery, the authors humorously use the contrast between Miles and Jack’s characters; they are alive!  The diversity between these two men is as broad as the Grand Canyon, but it works well in the storyline. In fact, there is continual tension between the two men, even though humorous, that really adds color to the story.  It is human satire at its finest.  Jack’s apparent manhood is centered on his ability to land a woman in bed. By contrast, Miles inability to get past rejection brings even more tension into the mix as they discuss their adventures with the two women the night before.  Shirtless Jack wants ever detail, but Miles is not amused, nor is he willing to share anything about his time spent with Maya.  Clueless Jack continues to try and force the conversation with big bear hugs, and flinging Miles on the bed kissing his cheeks, while affirming how “Proud” he is of him.  Miles considers this a private matter, and Jack says, “You’re kidding, right?  Tell me what happened you fucker, or I’ll tie your dick in a knot.”  The comical conflict continues until finally, in a near triumphant moment, Miles stands up to Jack and tells him that he cannot take it anymore.  “Just leave me alone, okay?  You’re fucking me up.”
While enjoying his passion for wine, Miles is on a journey of self-discovery. In Sideways, the author’s successfully use the banter between two old friends (Miles and Jack), the development of their opposite characters, and the conflict that arises in their relationship to push the plot forward and bring resolve in the end—Miles is able to move forward with his life.  There is resolve and resolution, which is essential in every story.




“Fade-in,” is the screenwriters version of “Once upon a time…” the announcement that a story is underway…the games have begun!  But, since screenwriting is written for a visual medium, the stakes are a little larger.  By that I mean, your opening image–what you create on the first page of your script is enormously important!  It is either going to hook your audience, or send them back to the snack bar for another round of popcorn, red licorice, and soda.


Yes, it’s very true.  The opening image is a visual that needs to draw the audience in.  In fact, it should set the tone and summarize the entire film.  You want to pick an opening image that can develop with the storyline, and expand on in a very dramatic way.  Think “impact!”  You want to impact an audience, not put them to sleep, and it’s important to remember that you don’t have time for exposition that is seen in a novel.  Au contraire…in screenwriting you want to bring the audience into the moment from the fade-in.  In other words, bring the audience into the A-C-T-I-O-N right away!

…stay tuned…