16 Straightforward Facts About ‘Sideways’

The Alexander Payne-directed Sideways followed two men in their forties taking a week-long trip to Santa Barbara, California. Ostensibly planned as an intimate bachelor party, soon-to-be-married Jack (Thomas Haden Church) and unsatisfied writer Miles (Paul Giamatti) end up getting romantically entangled with two women (Virginia Madsen and Sandra Oh), which they complicate in both comedic and horrific self-destructive fashions. Here are some facts about the 2004 movie that are best paired with a wine that’s still evolving.

1. Alexander Payne read the book on which the movie is based on a flight back from a film festival.

The director was flying back from Edinburgh, where he had been at a film festival promoting Election, when he finally had a chance to read Rex Pickett’s book Sideways. As soon as he landed, Payne ran to a pay phone (this was 1999) to call his agent about purchasing the rights. He later told Pickett he liked his novel because his characters were “so fucking pathetic.”

2. George Clooney wanted to play Jack.

Payne and Clooney met to talk about the part, then Payne lost touch with the actor. Seven years later, Payne cast Clooney in The Descendants.

3. Thomas Haden Church stripped down for his audition.

The Wings star was the only actor to take off all his clothes in the audition. He assumed the other candidates reading the scene where Jack is naked also went full-frontal. He was later shocked to discover that wasn’t the case.

4. Paul Giamatti knew nothing about wine.

The actor admitted to faking every bit of wine knowledge, and not understanding why anybody would care about it. He also claims he was shocked that he was cast in a lead role and initially thought it was a practical joke.

5. The actors drank grape juice. (At least some of them.)

Church estimated that grape juice or non-alcoholic wine was what they consumed 95 percent of the time. Conversely, Giamatti claimed the actors drank real wine, and that he was actually very drunk after shooting a dinner scene.

6. Miles’s favorite wine was originally something else.

Payne and the producers were denied permission to use Chateau Petrus Pomerol, a rare (and very expensive) Merlot, as Miles’s favorite wine. Chateau Cheval Blanc was Miles’s drink of choice instead; ironically, that too is a Merlot and Cabernet Franc blend.

7. Maya’s wine speech is personal to Payne.

Payne and his writing partner Jim Taylor based some of the speech on a passage from Pickett’s book, and included how the director himself feels about wine. However, he didn’t think the speech deserved as much praise as it received.

8. Church and Giamatti got food poisoning.

They got sick after eating at Miles’s mother’s house; at one point during filming, Church had a temperature of 104 degrees.

9. Payne denied ripping off Little House on the Prairie.

A reporter asked Payne if Miles running down the grassy hill was purposely evoking the opening credits to Little House on the Prairie. It was actually borrowed, with permission, from the thesis film of one of Payne’s former classmates.

10. Church was nervous about shooting a love scene with the director’s wife.

Sandra Oh, who played Stephanie, was married to Payne at the time. Initially Church and Oh played the scene as if it was funny, before Payne made the two act more and more passionate with each successive take. Payne and Oh divorced two years later.

11. The big naked man is only recognized by other men.

M.C. Gainey played the husband of Cammi, a waitress Jack seduces ... but whose husband comes home early and chases a naked Jack out of the house. Later, it’s Gainey who is doing the naked chasing. He once said, “Men recognize me from it, but I have yet to have a woman say, ‘Weren’t you in Sideways?’” Despite the “wonderful” experience, Gainey claimed it would be the final nude scene of his film career.

12. A scene in which Miles runs over a dog was cut.

It got the axe even though Giamatti’s facial expressions in the scene made it supposedly funnier than it sounded. Scenes where an agitated Jack calls his fiancée during his trip were also taken out.

13. Payne changed the ending of the book because it was “too Hollywood.”

In the book, Maya (Virginia Madsen) showed up at Jack’s wedding to say she sees Miles in a more positive light after reading his manuscript. After another few drafts, the soon-to-be Academy Award-winning script had the film ending with Maya’s message on Miles’s answering machine, then Miles knocking on her door.

14. Pinot Noir sales increased after the movie came out.

While Merlot sales were on the decline well before Miles professed his hatred of the varietal in the film, Pinot Noir sales increased by 16 percent in grocery stores throughout the United States after Giamatti’s character gave it a ringing endorsement.

15. Sideways was remade with Japanese actors.

Saidoweizu was set in Napa Valley, and made with Payne’s permission but without his involvement. Paul Giamatti rejected an offer to make a cameo.

16. Payne isn’t interested in the book’s sequels.

Miles and Jack traveled to Oregon with Miles’s mother in Rex Pickett’s 2011 sequel, Vertical. Pickett made Sandra Oh’s character into a lap dancer as a “little wave” to Payne, and wrote Stephanie (Terra in the books) out of Vertical entirely so Payne wouldn’t have to work with his ex-wife again. Pickett also wrote an ebook in 2015 titled Sideways 3 Chile, which found Miles traveling to South America.

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A version of this story was published in 2016; it has been updated for 2024.