Sideways
- 2 days ago
- 2 min read


Actor Paul Giamatti won a Best Actor award at last month’s Golden Globes ceremony for his memorable performance in The Holdovers, one of the best movies of 2023. In his acceptance speech, Giamatti thanked his director Alexander Payne, whom he called Alexander the Great. And for good reason! Payne has directed a number of terrific films over the past 20 years—strong character-centered dramas often distinguished by dark, comedic touches that vividly bring the struggles of the characters to life. Two of my favorite films directed by Alexander Payne are Nebraska and About Schmidt. But hands down, I love his 2004 movie Sideways above all others. In every way, it’s brilliant! And it stars, who else, but Paul Giamatti in one of his greatest performances.
The layers of their inner lives are neatly peeled back by the Oscar-winning screenplay.
Giamatti plays Miles, a wine connoisseur who takes his old college roommate Jack on a road trip through California wine country the week before Jack is to be married. While Miles is a lover of the grape—too much sometimes—Jack is a lover of women—again, too much sometimes. While Miles is excited at the prospect of playing golf with Jack and introducing him to the world of winemaking, Jack could care less. His goal is to meet and sleep with any woman he meets who will have him before he becomes a married man. and so, sideways quickly takes shape as a road movie as Miles and Jack pursue their opposite goals with hilarious results. Along the way, the layers of their inner lives are neatly peeled back by the Oscar-winning screenplay to reveal how the two men are struggling to cope with the disappointments of their midlife dilemmas. Jack is a has-been soap opera actor who now does TV commercials. Miles is a middle school English teacher who still grieves over his divorce from his ex-wife, while also desperately hoping that the novel he’s written will find a publisher.
All of this might sound awfully sad if not for the fact that both Miles and Jack are incredibly likeable, funny people—even with all of their flaws. You can’t resist hoping that they will somehow find a way to solve the tangled mess of their lives.
I give Sideways four out of four stars. To reveal any more of the story would spoil the rich layers of dramatic surprises and wonderful character moments that are crafted into the story, especially those involving the two women that our heroes meet along the way. In addition to Paul Giamatti, the stellar cast includes Thomas Haden Church, Virginia Madsen and Sandra Oh. Sideways is as exceptional as a glass of Chateau d’Issangi Margaux. Enjoy!



