Thomas Haden Church received his first Oscar nomination for portraying Jack Lopate in Sideways.
Thomas Haden Church portrays Jack who is in many ways the exact opposite of his friend Miles (Paul Giamatti). Jack is almost always happy, even when he gets mad or sad it is only for a brief period, opposed to Miles who is almost always is at least a little bit moody. Jack is just about completely amoral, and seems to have absolutely no sense of decency, where perhaps Miles has a little bit of it. Jack does not seem to be overly smart, where Miles at least could be described as a pseudo intellectual.
Their dynamic is a rather strange one, but both actors do manage to make their "friendship" believable they are able to stand each other, but they are definitely of two different sorts. Thomas Haden Church has actually quite a difficult part in that Jack's actions are quite unlikable through the course of the film caused by his amorality, also there is the fact that it does not seem he even learns anything after what happens to him. Jack could have very easily come off as just a despicable character that you don't want to even see, but Church manages to make the unlikable Jack likable.
Church does this in a rather interesting way, in that he almost portrays Jack as a child, which is the perfect way to portray. Everything Church really does as Jack seems slightly childlike. Church is careful to infuse this childlike quality to Jack to just the right degree, without making Jack seem unrealistic. It is interesting though just the way Church manages to bring a childlike quality to everything he does. His want for his last week of "freedom", and just the way he listens to Miles talk about has just the same enthusiasm and impatience of a child.
The negative qualities of Jack though are the real challenge, and Church meets the challenge. Church does this firstly by being charming in his rather simple, in more than one way, fashion that always feels quite effortless. Again though when he does wrong, and he really does a lot of wrong it is the childishness of Church's characterization that keeps him from somehow seeming completely despicable. Everything he does bad is almost just like a spoiled child that really does not know any better, even though he should.
Even when he suffers the consequences Church shows Jack to act in a childish fashion finding someone else to blame, or when he finds no other option pleading like a crying baby for help. Because Church manages to be so honestly pathetic he actually comes off as oddly endearing. I also really like his scenes where he attempts to cheer up Giamatti's because Church shows such a senseless happiness in the role. Jack really is a rather challenging role but Thomas Haden Church brings the perfect sort of life to the role through his simple but very well handled characterization. Jack is a role that could been just a jerk, but Church succeeded in turning Jack into a lovable jerk.