Sideways (2004) Scenes & Screenplay: Still Highly Drinkable

Removing some scenes included in the screenplay kept the movie from "going to the dark side" and continues to keep it highly drinkable.

The boys and girls have a good day. Copyright Searchlight Pictures.

This post is part of a series for the Newmarket Shooting Scripts, a collection of 88 screenplays published between the 1990s and 2010s by Newmarket Press. Below, scene numbers from the Sideways shooting script are referenced. You can grab a copy on Amazon or eBay. Enjoy!

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Why is a movie centered on a depressed man so comforting to me? At first I thought, oh no, it's because I'm depressed. But that didn't seem quite right. Sure, I've experienced my fair share of depression, but I think a lot of that was just boredom in disguise.

Do I love Sideways because I love wine then?

The movie, and now this script, did help me enjoy wine more, but that didn't seem right either. I'm more of a Jack than a Miles drinker when it comes to wine. Pour me a glass. I'll swirl it around and give it a sniff. But after that it could just as well be scotch or swill.

I think the real reason I love this movie is because it too is real. I believe these characters could exist somewhere in this world and we get to follow along on their adventure, complete with silhouetted picnics, golf course rage, and the awkwardness of falling in love.

But what is real? This question reminds me of the interaction between Miles and Jack's future father-in-law, Mr. Erganian, in Scene 14. Miles tells him that his novel is fiction, but that is draws upon personal life experiences, to which Mr. Erganian replies: “Good. I like non-fiction. There is so much to know about the world that I think reading a story someone just invented is kind of a waste of time.”

The irony is that we're experiencing this story called Sideways that's not real but invented. Of course, like Miles, the author of the book that the screenplay and movie are based on probably drew upon his own life experience when creating the story.

So, again, what is real? For me, the movie The Matrix and the children's book The Velveteen Rabbit have some good answers to this question, but to answer it in the context of Sideways, I believe real means being authentic, which Sideways achieves.

In the foreword of the shooting script, film critic Peter Travers says, “On the surface, Sideways has all the makings of a bottom-feeding buddy farce—a forty-something American Pie. Hollywood would love to make that movie. Alexander Payne, bless him, would rather die."

Travers also said that reading the screenplay before or after seeing the movie is like "pairing oysters with an ethereal Chablis." I'm not interested in pairings—at least not yet—but Sideways finds a way to stand on its own, year after year as I watch it annually like I do other movies including Adventureland (2009). Though different in character and story, they are both real and, more importantly, highly drinkable.

Alexander Payne who directed and co-wrote the screenplay for Sideways with Jim Taylor seems responsible for keeping the movie grounded, or, like Miles might say. "tight as a nun's asshole." (Scene 46)

In the screenplay, some unfortunate scenes fortunately did not get made, or were cut. They're scenes that A24 filmmakers would, as Travers might say, "love to make" that have Miles boarding an open boat in a dark and timeless underworld (Scene 68) and walking an unstable, narrow rope bridge over a deep canyon (Scenes 70, 139).

I'm hopeful that Miles, as a writer, would even protest if these scenes made it into the movie and say something like he does at the Hitching Post in Scene 137.

“Tastes like the back of a fucking LA schoolbus. Probably didn't de-stem, hoping for some semblance of concentration, crushed it up with leaves and mice, wound up with this rancid tar and turpentine mouthwash bullshit. Fucking Raid.”

Sorry, Jim! You're still a legend, and I thank you and Alexander dearly for the other scenes. While I may not be depressed, I can be melancholic, and scenes like the silhouetted picnic scene have the ability to lift me right up out of it.

Spoilers ahead: Go watch (or rewatch) the movie if you haven’t seen it already (or in a while), then report back in the comments with your favorite scene!

My favorite scenes from Sideways

Reading the screenplay for the first time after seeing the movie so many times, I was able to notice little moments in the script that contributed to making the movie so special and real. Some of these little moments are my favorite scenes.

That said, Payne did an excellent job removing the little moments that would have made the movie just a bit too real, like Scene 95 with Miles hitting the dog with his Saab and, days later, passing by it as roadkill in Scene 143. Oddly enough, there's a comedy to these scenes when reading the script because they show us that, no matter how shitty life gets, life goes on, as it does for Miles. This sentiment is tastefully sustained in the final cut.

How to watch the scenes: Rent or buy Sideways on YouTube and use the timestamp links below. If you already own the movie, link your license to YouTube with Movies Anywhere. You must close YouTube before watching consecutive scenes due to a glitch, but this method is still the best way to rewatch your favorite movie scenes and support the movie. Some scenes are embedded below, but only studio-approved scenes on Movieclips. You can watch all the Movieclips scenes for Sideways here. Now, back to the show!

Miles steals money from mom

Scene 30 | 0:13:01 | Screenplay and movie

Miles stealing money from his mom's dresser reminds me of how you're never really alone when doing something bad. It always feels like someone is watching. In this scene, it's himself and his family watching—photos of them, happy ones. When I read this scene, I imagined Miles longing for returning to a time when he was happy.

INT. MILES'S MOTHER'S BEDROOM - NIGHT

His task complete, he closes the drawer, and as he stuffs the bills in his pocket, his glance falls upon FRAMED PHOTOS atop the dresser--

–- A proud NINE-YEAR-OLD MILES poses in front of his childhood San Diego home, showing off a WAGON filled with freshly harvested lettuce. On the wagon is a hand-lettered sign -- "10 cents a bunch."

-- A Sears portrait shows the RAYMOND FAMILY: a much younger Phyllis, her husband, and their two children -- a 12-year-old Miles and seven-year-old Wendy.

-- Miles at his wedding. He and his bridge VICTORIA look young and attractive, their faces radiant and hopeful.

I would have loved to see the wagon photo of Miles selling lettuce, but we see a picture of Miles with his father instead in the movie.

Jack has an American Pie moment

Scene 65 | 0:37:54 | Screenplay only

No new, racy lingo from Sideways caught on like MILF from American Pie, but the screenplay in particular has a few gems I'll be keeping in my backpocket, including Assylvania.

INT. MOTEL ROOM - DAY

Miles pulls himself out of bed and slouches toward his suitcase.

JACK (CONT'D)
Fucking chick in the Jacuzzi -- goddamn, Miles, fucking going nuts up here. Whole place is wide open. Assylvania.

I think Assylvania suits Jack’s character well, but I guess it was too American Pie. The movie would become a favorite movie among two-glass-a-day mothers and grandmothers after all.

Miles protests merlot

Scene 66 | 0:39:01 | Screenplay and movie

Because of this scene, there was a decrease in merlot sales upon the movie's release. According to Northern California Public Media, "USDA figures show that merlot plantings in California declined 35 percent between 2004 and 2023 [while] pinot noir acreage almost doubled."

EXT. LOS OLIVOS - NIGHT

JACK
Do not sabotage me. If you want to be a lightweight, that's your call. But do not sabotage me.

MILES
Aye-aye, captain.

JACK
And if they want to drink Merlot, we're drinking Merlot.

MILES
(dead serious)
If anyone orders Merlot, I'm leaving. I am not drinking any fucking Merlot!

I can only remember buying Merlot once after seeing this movie out of curiosity. Is it really that bad? I thought it tasted fine, but, again, I’m a Jack drinker.

Miles forgets the shower curtain

Scene 106 | 1:13:54 | Screenplay only

It's unbelievable how much wine Miles and Jack drink on the trip and are still standing, though the story remains real because of the nuanced slip-ups included in the script. They are not just fictitious characters after all. They have little quirks and make little mistakes like the rest of us, including Miles forgetting to put the curtain inside the tub before taking a shower.

INT. MOTEL ROOM - NIGHT

THROUGH THE BATHROOM DOOR --

Miles takes a nice hot SHOWER. But wait -- he has forgotten to put the shower curtain inside the tub. A closer look reveals a growing PUDDLE OF WATER on the floor.

This scene did not make the movie, but the spirit of Miles' clumsiness comes through in many other ways.

The boys and girls have a good day

Scene 118 | 1:20:00 | Screenplay and movie

My hope is that you've had some nice days like this. I surely have, even though it can be hard to remember them sometimes. They help you through the darker days. They help you remember how sweet life can be… how sweet life is.

EXT. IDYLLIC PICNIC SPOT –- DAY INTO DUSK

The girls have led them to a beautiful spot.

IN A SERIES OF SHOTS --
we see the progress of their picnic. We don't hear them, but there is a growing intimacy about their interaction. Even Maya and Miles seem to be overcoming residual awkwardness from the other night. Jack and Stephanie lean on each other as they eat and sip wine.

Finally, the two couples are SILHOUETTED against the SUNSET.

One of my most memorable days of last fall was having a picnic with champagne and charcuterie with a girl in our local park. We sat on a hill watching the sunset and she commented about how the trees had become silhouettes.

Miles guzzles the spit bucket

Scene 141 | 1:32:07 | Screenplay and movie

I've never expressed frustration in public in such an extreme way. This is inspiring. Instead of calling the wine pourer a bad name, Miles drinks from the spit bucket. That's courage!

POURER (CONT'D)
You're going to have to leave, sir.

The pourer signals to a SECURITY GUY at the door. Across the room Jack notices the disturbance and heads over.

Miles hoists up the SPIT BUCKET, holds it aloft and starts to GUZZLE IT. Wine cascades down the sides of his face, onto his shirt and even onto his shiny new shoes.

The Security Guy yanks the bucket away from Miles, and drags him toward the EXIT. Jack catches up.

JACK
(to the horrified onlookers)
It's all right. His mother just died.

For some reason, I appreciate that last line from Jack more and more every time I watch it. It further reinforces his character as a quick-witted brute.

What’s your favorite scene?

Did you read the Sideways screenplay or watch the movie? If so, leave a comment below with your favorite scene. I’d love to know about it.