The Sideways Trilogy

It’s seven years after the events of Sideways. Miles has written a novel that has been made into a wildly successful movie, and the movie has changed his life. Jack, contrarily, is divorced, has a kid, and is on the skids. Phyllis, Miles’ mom, has suffered a stroke that’s left her wheelchair-bound and wasting away in assisted living. She desperately wants to live with her sister in Wisconsin. When Miles gets invited to be master of ceremonies at the International Pinot Festival in Oregon, he hatches a harebrained road trip.

Sideways: Chile follows the further adventures of Miles Raymond (played by Paul Giamatti in the critically acclaimed movie Sideways). It’s now a few years later and Miles is a successful author with a blockbuster movie adaptation under his belt, but he’s still searching for something, and depression has him, once again, in its taloned grip.