Miles Raymond, protagonist of the Sideways movie, is a flawed character I can’t help rooting for. But is he a hack, a fraud? Let’s explore!

And I know, Sideways movie review? Am I turning into an artsy critic? Don’t worry, your boy wouldn’t do you dirty like that. I only want to touch on if Miles, played beautifully by Paul Giamatti, knows what he’s talking about when it comes to wine. And, spoiler alert, I’m here to defend him.

I really can’t help it; I like Miles. After all, I can somewhat relate to him. He clearly enjoys wine and he’s attempting to be a writer at an older age. Both are true for me as well. And that’s where I want to start:

Understanding Miles Raymond

Sideways begins and it gives us a glimpse into what we can expect out of our protagonist: He wakes… correction, he’s woken up abruptly because he has parked in a way that a truck can’t enter the condominium. Miles “didn’t park too good” because he was, irresponsibly, driving drunk the previous night. He’s also late.

But his haste only lasts as far as lying to Jack, his friend, on the phone about why he’s late. Miles then takes his sweet old time in the toilet and shower, stops for a coffee and a spinach croissant, and leisurely drives while filling out a crossword puzzle. No rush whatsoever, he can always blame his extra tardiness on heavy traffic. Later we’ll see Miles stopping by his mother’s home to say hello before her birthday. Well, that’s the excuse. He likely only stopped to get a free meal and steal some money from her before sneaking out at the crack of dawn.

Yup, our Sideways movie protagonist is a depressed alcoholic still not over a divorce that happened two years ago. He’s also a selfish liar with anger issues. Why do we like him, again?

Well, why do I like him is the proper question. Other than some things in common, I mean.

How the Sideways Movie Redeems Miles

Well, Sideways is a movie. We’re shown an exaggerated version of reality. A character must be established, the plot will move them for better or worse, they will follow an arc, and in some instances, find redemption. All of that in roughly two hours.

We’re quickly introduced to Miles’ flaws; that’s the Sideways movie establishing what we can expect from him. The redemption, on the other hand, is a slow burn. We need to see Miles spiraling down before we get somewhere with him. It’s better that way, don’t you agree?

Throughout the film we see our hero evolve, even when he’s out of control. Closer to the end of the movie he helps Jack stage an accident and recover a wallet. He also, eventually, is truthful to Maya. A big step for a liar.

Maya, by the way, is the love interest, and even though the resolution is up in the air at the end of the Sideways movie, it’s a sweet love story. She’s the one that re-rails Miles, in a way. I think she genuinely likes him. And, if she does, why shouldn’t we?

Lastly, he enjoys wine. He’s a bit snobby and even maybe a phony in some scenes, but he knows enough about it. His passion is contagious, and that led to what’s called the Sideways effect. Pinot Noir—his favorite wine—sales saw an increase after the movie, but Merlot experienced the opposite.

How The Sideways Movie Harmed Merlot. And Why

If anyone orders Merlot, I’m leaving! I am not drinking any fucking Merlot!

Miles Raymond

The quote above is from one of my favorite scenes in the movie. Miles is, of course, depressed and not sure he wants to go on a double date, even when he likes the girl. The friends are outside a restaurant and Jack is demanding he don’t sabotage the evening. Asks him to not drink too much and to behave. Then he says: “if they want to drink Merlot, we’re drinking Merlot”, which elicits Miles’ memorable line.

It’s fair to say that the Sideways movie was popular and it got a lot of people interested in wine. Of course, his thoughts on Merlot resonated amongst buyers, and influenced sales. Conversely, Miles is passionate about Pinot Noir, and he describes it poetically. Real world interest for this varietal skyrocketed.

Right, but what’s wrong with Merlot? Why would Miles angrily put his foot down outside the restaurant? Does Miles really hate Merlot that much?

Does he hate it at all?

It’s time we address the elephant in the room.

“I Guess the Star Would Be a 1961 Cheval Blanc”

In one scene in the Sideways movie Maya asks Miles about his collection. He admits that it’s not much of one, he never had the money for one. He does, however, have a whopper. A 1961 Cheval Blanc.

Cheval Blanc is a right bank Bordeaux red blend, and 1961 was an exceptional vintage for Bordeaux wines. A blend of what? you ask. Merlot and Cabernet Franc. That’s right! Miles’ star in his collection is a Merlot blend! Maybe he is a hack after all!

Now, I’m being cheeky. See, the ’61 Cheval Blanc is a predominantly Cabernet Franc blend. Information online varies, but all agree it’s around 60/40 Cab Franc. So, Miles is saying some Merlot is fine, but only blended, right?

Not so fast. Elsewhere, this is Miles about that other varietal: “I’ve come to never expect greatness from a Cab Franc.” Am I still going to defend him? I mean, the case for Miles being a fraud is pretty strong, wouldn’t you say?

Miles Raymond Is Not a Hack in the Sideways Movie

Let’s think about it. Miles truly enjoys wine, and he knows quite a bit about it. Early on Jack mentions that he thought that Miles didn’t like Chardonnay. He answers back: “I like all varietals. I just don’t like how they manipulate Chardonnay in California. Too much oak and secondary malolactic fermentation.”

I admit I had the same experience in the early aughts. My first Chardonnays were from Chile and California, and I just didn’t enjoy the excessive oak in them. It took a decade for me to give the varietal a second chance when I was introduced to the fresher more balanced French style. So, Miles knows what he’s talking about. Even his lingo is spot on.

Additionally, first to Jack and then to Maya, he talks about Pinot Noir and why it’s a special grape that makes spectacular wines. He also has other accurate things to say about wines they drink throughout the movie. To me it’s clear that he knows enough about wine to know that his Cheval Blanc is a Merlot Blend. I will go further and say that he purchased the bottle not because it had more Cabernet Franc than Merlot, but because 1961 was an exceptional vintage.

So, What’s His Deal with Merlot?

Well, there’s two things, and neither are explained in the Sideways movie, so I understand why many might’ve missed them.

One of them is in the book the movie is based on. See, in the book Merlot is explicitly stated as Miles’ former wife’s favorite wine. He rejects Merlot for sentimental reasons and for the painful memories it brings. I get it. It’s like hearing that one song on the radio and you rushing to switch it off.

The other thing is the state of Californian Merlot in the turn of the millennium. Winemakers were making mostly cheap and poorly made Merlot. It was a popular wine, so producers were careless and quality was unimportant. So, like what we heard earlier with Chardonnay, it’s easy to understand why he would be skeptical about a random Merlot ordered in a restaurant. Of course, wine people back then would’ve been aware of this, so they understood. What was unexpected was how popular the movie was, and how it was to shape the wine industry.

Well, ok, but what about Cabernet Franc, then?

I am unaware of how well-made—or not—were Cab Francs in California during the times of the movie. I don’t remember having tasted any of them back then. Maybe something from Loire, but it would be several years before I tasted great ones, first in Argentina and eventually Chile.

Either way, I get now that Miles understood that there’s a difference between Merlot and Cabernet Franc produced in California versus the ones produced in Bordeaux. And there, again, I can relate. I never order (New World) Merlot in a restaurant, but I would a Saint-Émilion or a Pomerol.

The Last Drop

No. I don’t think Miles Raymond is a hack. He is extremely flawed, but he needs to be to keep the story interesting. He’s also a wine snob and pompous when tasting wines. There’s a scene where he has a finger to his ear, like a musician looking for a natural pitch, when smelling the wine, which is both funny and cringe.

In the end, Miles walks out of Jack’s wedding to grab his Cheval Blanc from his closet. I’m not sure that’s the best spot for long-term storage of wines, but I’ll let it go here. He takes it to a burger joint, hides it in the booth, and drinks it from a plastic or Styrofoam cup, pairing it with a hamburger and onion rings. Who needs proper wine glasses, right? He still enjoys it. It’s like Maya told him: “The day you open a ’61 Cheval Blanc, that’s the special occasion.”

Have you seen the Sideways movie? And have I convinced you that Miles is not a fraud? Either way, let me know down in the comments. I’m always happy to talk more about this film.

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Cover Image: The Sideways movie cast: Sandra Oh as Stephanie, Thomas Haden Church as Jack, Virginia Madsen as Maya, Paul Giamatti as Miles.