Sideways (2004)

100 Films’ 100 Favourites #84

In search of wine.
In search of women.
In search of themselves.

Country: USA & Hungary
Language: English
Runtime: 127 minutes
BBFC: 15

Original Release: 22nd October 2004 (USA)
UK Release: 28th January 2005
First Seen: cinema, 2005

Paul Giamatti (Big Fat Liar, Shoot ‘Em Up)
Thomas Haden Church (George of the Jungle, Spider-Man 3)
Virginia Madsen (Candyman, The Number 23)
Sandra Oh (Under the Tuscan Sun, Hard Candy)

Alexander Payne (About Schmidt, Nebraska)

Alexander Payne (Jurassic Park III, The Descendants)
Jim Taylor (Election, I Now Pronounce You Chuck & Larry)

Based on
Sideways, a novel by Rex Pickett.

The Story
Middle-aged wine lover Miles takes his friend, groom-to-be Jack, up to California wine country for a more mature kind of bachelor trip, but Jack’s lascivious ways lead them to become involved with a pair of women — while keeping Jack’s impending nuptials a secret…

Our Hero
Miles Raymond is a divorcee, a teacher, and an unpublished novelist, depressed at the state of his life. His one love is wine appreciation, though when Jack goads him into getting closer to a waitress he casually knows, Maya, things begin to look up.

Our Villain
Jack, a has-been actor and Miles’ college roommate. Not really interested in wine; very interested in women — even though he’s engaged, he hooks up with Maya’s friend Stephanie, not telling her about his imminent marriage. Not strictly a villain, but his antics bring Miles little but misery.

Best Supporting Character
Maya is a waitress at Miles’ favourite restaurant, and they bond over a shared appreciation of wine. Unfortunately, her friendship with Stephanie and the secret of Jack’s engagement poses a threat to her burgeoning relationship with Miles…

Memorable Quote
“If anyone orders Merlot, I’m leaving. I am not drinking any fucking Merlot!” — Miles

Quote Most Likely To Be Used in Everyday Conversation
See above.

Memorable Scene
Jack hooks up with a random waitress but has to flee when her husband comes home, leaving his wallet behind with the wedding rings inside. He gets Miles to take him back to her house, where Jack convinces his friend to sneak in to find the wallet. Inside, the waitress and her hubby are having sex, but they spot Miles grabbing the wallet — so he’s chased back to the car by a very angry naked man. (It’s not exactly the film’s cleverest bit, but it is memorable.)

Making of
Sideways was so popular, it actually had an effect on the wine market. Miles is famously critical of Merlot (see above), which actually caused its sales to drop in the US and UK. However, there was a bigger impact on Pinot Noir, which he expresses a love for. After the film’s release, sales of Pinot Noir wines increased by over 20% compared to the year before. The effect lasted, too: a 2009 study found that sales volume of Merlot had slowed and its price had dropped, while sales and prices of Pinot Noir were still up.

Next time…
Author Rex Pickett has penned two sequel novels, Vertical and Sideways 3 Chile, but Alexander Payne has said he has no interest in adapting them and, though Fox owns the rights to the characters, they have no interest in making sequels without Payne. Of gossipy interest, however, is that Pickett deliberately wrote Sandra Oh’s character out of the sequels, because the actress made script changes he disliked and he didn’t want to work with her if they did make a sequel.

1 Oscar (Adapted Screenplay)
4 Oscar nominations (Picture, Supporting Actor (Thomas Haden Church), Supporting Actress (Virginia Madsen), Director)
1 BAFTA (Adapted Screenplay)

What the Critics Said
“how different these two characters are: the crass actor and the sensitive writer, linked by being roommates at college, but by little else these days. Viewers will probably identify with one or the other, but the beauty of the script is that these are rounded, believable people with recognisable failings and strengths — one is not superior than the other. So, while Jack is a bit dim, crude, and thinks largely with his crotch, he’s also enthusiastic, loyal and embraces life. And while Miles is funny, clever, and knowledgeable, he is also timid, drink-dependent, and crippled by insecurity” — Nev Pierce, BBC Movies

Score: 96%

What the Public Say
“This performance made [Thomas Haden Church] a star, earning him roles in everything from Spider-Man 3 to Easy A. By turns charming and crass, his laconic man-child is a perfect foil to the tightly-wound Miles, and their chalk-and cheese riffing is minded to fine comedic effect at times, most notably in Miles’ horrified discovery that Jack has been chewing gum throughout his detailed tutorial into wine tasting. It’s Giamatti’s picture though. He makes Miles vulnerable, sarcastic, grouchy and tender – sometimes all at the same time. He’s capable of expressing a depth of emotion with nothing more than a flicker in his eyes or furrowing of his brow. It’s a performance he’s never bettered.” — Rob D, Random Movie Guy


Do you ever watch a film, like it well enough, but then find that, without re-watching or consciously re-evaluating, it sneakily grows in your estimation? That was Sideways for me, after I saw it on its original release. I’ve watched it a few more times since which have cemented my opinion. It’s a pretty perfect example of the comedy-drama, being both very funny but with a core story based in characters going through emotional crises, whether they know it or not. It’s a deceptively gentle film, the kind of movie where it can seem like nothing’s happening, but the cumulative effect builds to a nice, complicated aftertaste. Like a fine wine, then.

I see #85 walking around like regular movies.

5 thoughts on “Sideways (2004)

  1. I’ve only seen this once, back in the Lovefilm rental days (a distant epoch now) but I recall I rather enjoyed it. Maybe I should get around to a rewatch sometime. It reminds me of a Kevin Costner coming-of-age film, Fandango. They are a certain type of film. Small-scale character drama/comedies that for some reason leave a mark on you. If I made a personal top 100, it’d be Fandango rather than Sideways, but it’d be in there for the same reason.

    Liked by 1 person

      • Crikey, yes. Its a 1985 film directed by Kevin Reynolds and was (I think) Kevin Costners first film (or certainly his first starring role anyway). They would go on to make Robin Hood and Waterworld together but Fandango has more heart than both blockbuster movies. Its a 1980s American Graffitti (although set in 1970 I think). Well worth searching out, I think you might love it. Its a coming of age film that clicked with me on a personal level (growing up, leaving youth behind) and its pretty damn funny in places.

        Liked by 1 person

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