Miles and Jack are back. It’s seven years later. Miles has written a novel that has been made into a successful movie, and the movie has changed his life. Jack, contrarily, is divorced, has a kid, and is on the skids. Phyllis, Miles’s mom, has suffered a stroke that’s left her wheelchair-bound and wasting away in assisted-living. She desperately wants to be with her sister in Wisconsin. When Miles gets invited to be the master of ceremonies at a Pinot Noir festival in Oregon, he hatches a harebrained road trip. With Jack as his co-pilot, he leases a handicapped-equipped rampvan, hires a pot-smoking Filipina caretaker and, with his mother’s rascally Yorkie in tow, they take off for Wisconsin via Oregon’s fabled Willamette Valley. Hilarious, steeped in wine, Vertical’s tragi-comic-epic journey takes Sideways in a new and ultimately deeply moving direction.