The Sideways Trilogy

Sideways is the story of two friends, Miles and Jack, going away together for the last time to steep themselves in everything that makes it good to be young and single: pinot, putting, and prowling bars. In the week before Jack plans to marry, the pair heads out from Los Angeles to the Santa Ynez wine country.

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 3 Chile follows the further adventures of Miles Raymond (played by Paul Giamatti in the now cult movie Sideways) and, to a lesser extent, his friend Jack. It's now 10 years later, and Miles is a successful author, but he's still searching for something; depression has him, once again, in its taloned grip.