Early one morning while everything seemed difficult and problematic as usual, Miles (Paul Giamatti) wakes up to a neighbor knocking on the door telling him to move his car.  Miles, an interesting character in his own right, suffers internally from his long ago divorce that keeps him in a prolonged depression.  He feeds this depression with his preoccupation of negative thinking, which even oozes from his poor appearance and his untidy tiny apartment.  He is the kind of guy most would steer away from, as his presence provides contagious negativity.  He sees himself as a failed writer that tries to get by in life teaching English while the students probably openly disrespect him.  The essence of his character has all of the negative traits of a lonely middle-aged man that has hit a middle age crisis and believes that there is nothing better for him in life than a bleak, sad, passé, and isolated existence.  

Miles returns to the apartment while being aware that he is behind schedule, as he has over slept.  Over the phone Miles excuses himself, which he probably does frequently, for being late while he still finds a moment to escape reality through the thousands of books that cover most of his apartment.  The apartment alone tells more than a thousand words in regards to Miles' situation in life, as all the books suggest that he must be escaping reality as often as he can.  Besides having a fetish for books Miles also dreams of having his own vineyard, which explains his inclination for wine.  Wine is also the reason for why he has overslept, as he recovers from last night's hangover and begins his journey to meet his friend Jack (Thomas Haden Church).

These two middle-aged men have decide to venture through the Californian wine land while visiting as many vineyards and golf courses as possible over a period of six days.  The reason for this expedition is Jack's upcoming wedding, as they have decided that Jack should enjoy freedom before marriage one final time.  One striking notion is how Jack could be friends with Miles, as Jack is the polar opposite of Miles.  Jack has a career and options to try new things while being a positive, strong, and confident man who seems to have it all.  Why would a person such as Jack hang out with Miles?  Well, this question will answer itself, as Jack is the kind of guy that most people like to know, but only until the moment his true self appears.

Middle-age depression compiled by feelings of unworthiness, poor self-esteem, professional rejection, loneliness, and much more seem to be the reason why Miles welcomes Jacks presence.  After all Miles is the key for Jack to be able to be himself - a first-class jerk.  Jack's persona reveals itself when the audience hears Jack say, ""...I was dying in there." in regards to his new family and wife to be.  This, however, could be Jack expressing his anxiety for the wedding by having cold feet.  Later, in the film, more of Jack's two-facedness will become more consistent which only exists in order to serve his own personal desires without consideration for others.  Jack's career as an actor truly seems to be self-servant for him, as he cheats his way through conversations by deceiving people to like him.  Also, somewhere under this exterior Jack seems to have some form of a confused ego that only lives in the present.  Miles seems to be the only one who is aware of Jack's true nature, but accepts it due to his psychosocial status.

Sideways turns into an likable dissection of these two characters, as they will find a crossroad through golf, wine, and women.  On their way to this crossroad Miles will explore his own and other's existence and character, which will give him an opportunity to expand sideways.  Miles realize that he does not have to try to move forward to find what he needs.  Much of this Miles owe to Jack who is the catalyst that pulls him out of his own miserable void.  Yet, Miles does not approve of Jack's methods, which places him in a conundrum.  As an interesting side note, Conundrum is also the name of the publishing company that might publish Miles book.

Words such as vibrantly alive and authentic come to mind when listening to what the two main characters say.  This is due to a brilliantly adapted screen play by Alexander Payne who co-wrote the screenplay with Jim Taylor, which originates from a novel by Rex Pickett.  Illustrative, the communication between Miles and Jack displays their friendship by default, as the chemistry between the two transparently exhibits each character's psychology and their interaction with their present social environment.  Ultimately, Paul Giamatti and Thomas Haden Church's character contrasts makes the film very absorbing while providing performances of the highest level.  The female antagonists performed by Virginia Madsen and Sandra Oh help augment the characteristics of these two, in their own way, pathetic men.  This leaves the audience with an authentic tale of existence, hope, and love, which makes it ok to dream while also trying to work toward those dreams.

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