I have this list in my head of top quirky comedies and Sideways is definite on that list.
I think that magic for me is in the tempo of the movie, it takes it time to dwell on awkwardness and unsympathetic characters.
The whole idea of two guys going on a wine tasting trip in California as way of sending one of them into marriage is rather different, but makes a great story-line.
It seems I'm much more into these kinds of movies than Niels, but hell, that's what differences are all about =)
Good acting, simple plot, interesting story and a few good laughs. If your are into wine, this will probably be right up your ally. It is quite interesting how this movie seriously affected the marked for pinot wine.
A recommendable TV movie.