Favourite Duos #6 - Miles Raymond and Jack Cole (Sideways)

Credit to amathusdrinks

If you haven't seen the movie Sideways, I recommend it. This has another classic example of a dynamic duo. I originally heard about them from Doug Walker's "Top Ten Favourite Characters" countdown, and I apologise if I'm treading the same ground.

Miles is a divorced English teacher and struggling writer with a drinking problem. His best friend Jack is a soon-to-be-married, past-his-prime actor and serial womaniser. The two long-time friends are going on a road trip through the vineyards of Southern California, which is to serve as Jack's bachelor party, but both have hidden agendas: Miles simply wants to drown his sorrows, and is essentially using Jack as an enabler for this; Jack wants to have one last fling before he settles down, and hopes to find a partner for Miles as well.

Sure enough, Jack meets a wine pourer named Stephanie, and they immediately hook up to the point where Jack is willing to move house to be with her. Meanwhile, Miles meets a waitress named Maia and develops a connection, but is too timid to take things further. This establishes them both perfectly, with Jack's impulsive nature with little regard for the consequences of his actions, and Miles' tendency to play it safe and take little chances.

These contrasting flaws provide an excellent dynamic, allowing the two to complement one another. While they are both terrible people, they do genuinely care for one another. Their flaws essentially cancel each other out. Jack would be making too many poor choices if Miles wasn't there to hold him back, and Miles would be stuck in his self-destructive comfort zone if Jack wasn't there to push him forward.

Again, this is another dynamic I wish to borrow from. Instead of a "big one and little one" or "brawn and brains" duo, we have a duo in which one character is too impulsive while the other is too cautious, so there's a happy medium between the two.