When Sideways hit theaters 20 years ago, it made a lasting impact on the wine world—a phenomenon now known as the “Sideways effect.” Almost overnight, interest in Merlot literally went sideways while Pinot Noir became the darling of wine enthusiasts everywhere. The Santa Ynez Valley, where the movie was set, also saw a surge in visitors, with Sideways-inspired tours springing up and putting the region on the map.

Even today, the film’s influence lingers. Wine lovers still seek out the iconic tasting rooms and restaurants featured in Sideways, and the movie’s legacy continues to shape how people think about Pinot Noir and the Santa Ynez Valley wine scene. In case you’re wondering, Merlot has made a small comeback in the wine world, but Pinot Noir’s allure still remains supreme.

The Movie Premise

Sideways is a 2004 comedy-drama that follows two middle-aged friends, Miles (Paul Giamatti) and Jack (Thomas Haden Church), on a week-long road trip through Santa Barbara Wine Country. Based on the novel by Rex Pickett and directed by Alexander Payne, the film weaves humor with cynicism as the unlikely pair set out to celebrate Jack’s upcoming wedding in very different ways. Miles, a socially awkward writer and wine fanatic grappling with a stalled career and recent divorce, hopes for a quiet week of wine tasting and bonding. However, Jack, a carefree actor about to get married, is more interested in sowing his wild oats one last time. Along the way, their encounters with two local women spark philosophical discussions and moral debates, leaving both men questioning the paths they’re on.

Fun Facts

• Paul Giamatti was a total wine novice. It might surprise you, but Paul Giamatti knew nothing about wine before filming Sideways. He managed to convincingly portray a wine aficionado, faking his way through some of the most iconic scenes!
• Alexander Payne, on the other hand, was already a wine enthusiast. The director’s love for wine was a driving force behind the film. Payne purchased the film rights to Pickett’s book, which was published just a month before the movie premiered. Payne even co-wrote Maya’s memorable speech about wine, using inspiration from the book as well as his personal feelings about wine.
• The movie’s title is a nod to intoxication. In the book, the term “sideways” is used by the main characters to refer to being intoxicated.
• The movie was filmed over 10 weeks in Santa Barbara. Filming took place throughout October and November 2003, and the movie was released a year later on October 22, 2004.
• The actors got real-life lessons in wine. Before filming started, actress Virginia Madsen, a waitress in the movie, spent time in the kitchen and bar of Hitching Post 2 to get the feel of what the job was like. She and actress Sandra Oh also went to the Hitching Post winery to see the winemaking process first-hand.
• The film received widespread acclaim. After its release, Sideways went on to win an Academy Award, two Golden Globes, a Screen Actors Guild Award, and several Independent Spirit Awards, among others.
• Pinot Noir sales skyrocketed. Thanks to Miles’ deep love for Pinot Noir—and his infamous disdain for Merlot—sales of Pinot Noir on the West Coast increased by ~16% for several years following the film’s release.
• Sideways reshaped wine culture. The movie didn’t just change the wine world; it changed how we talk about wine. It made wine appreciation feel more approachable, helping to normalize the idea of being an everyday wine enthusiast without all the pretense.

Celebrating the 20th Anniversary

To mark the 20th anniversary of Sideways this month, Hitching Post Wines, along with Searchlight Pictures, is hosting a series of events. These include a special screening of the film followed by a Q&A with director Alexander Payne and actor Virginia Madsen at Copia at CIA in Napa on Saturday, October 12. On October 22, attend a special Sideways screening and meet and greet at Santa Barbara’s Hotel Californian. In addition, there’ll be a Sideways winemaker dinner at Suzanne Tracht’s Jar in Los Angeles on October 29, featuring Hitching Post Wines’ Frank Ostini and Gray Hartley, and another at Akasha in Culver City on October 30.

If you want to fully immerse yourself in the Sideways experience, you can still visit many of the film’s iconic locations. Enjoy a meal at the Hitching Post 2 or Los Olivos Wine Merchant & Cafe, or stay at what is now called the Sideways Inn (formerly the Windmill Inn). Santa Barbara wineries like Foxen, Firestone, Fess Parker, Sanford, Fiddlehead, and Kalyra, all featured in the film, remain must-visit stops for fans looking to retrace the characters’ journey and many sips.

As a special nod to the film, Hitching Post Winery has released a limited-edition 2021 Highliner Pinot Noir with a Sideways label, commemorating the wine that became so central to the story.