Directed by Alexander Payne, this 2004 comedy-drama starred Paul Giamatti and Thomas Haden Church. It was a very popular film at the time, praised for its witty script and excellent performances.

It’s kind of like a matured, Americanised version of cult classic Withnail & I.

And as Sideways heads for its 20th anniversary, we think now is a good time to uncork this SOB and sniff its aromatic delights. Innit.

Oenophiles and Sideways Lapses With Mid-Life Shenanigans

Righto, the plot is about one Miles Raymond (Giamatti). He’s a middle-aged English teacher living in San Diego and he dreams of becoming a famous published author.

A big wine buff, he’s still lingering on his divorce to Victoria (Jessica Hecht) and is depressed about it all.

With his friend Jack Cole (Haden Church) soon set to be married, the pair head off to Santa Ynez Valley wine country as a kind of stag do thing.

Miles wants a peaceful experience with sophisticated discussions about wine.

However, Cole is a kind of James Hunt (of F1 fame) type lovable rogue and wants nothing of it, immediately hitting on barmaid Stephanie (Sandra Oh) and starting an affair.

Miles also meets Maya (Virginia Madsen), who he becomes friendly with and casual flirting commences.

Still hung up on Victoria, however, Miles finds it difficult to move on. But Jack encourages him to pursue Maya.

He takes a shine to her after a deep and meaningful discussion about wine one evening, leaving him with his jaw dropped.

However, despite signs of a budding romance he continues to drink too much wine and becomes further depressed when his literary agent calls him to explain his book isn’t being published.

Frustrated, he becomes passive-aggressive and troublesome. In between such antics, he and Jack find time for a relaxing spot of golf.

Their local reputation takes a bit of a dive, not helped by the antics of Cole as he screws around and strings Stephanie along (mindlessly informing her he’s fallen in love).

She eventually finds out and assaults Jack, breaking his nose (kind of a problem when your wedding day is looming).

After this scene, Jack has an emotional breakdown explaining his life is ruined if his marriage is called off.

Troubled by this outburst, Miles agrees to stage a small car accident into a tree to explain for Jack’s broken nose. But his car veers off into a ditch when the attempt goes wrong.

Miles is left ruminating over (if not outright ruing) a bizarre weekend, whilst Jack returns full of swagger and charisma for his wife-to-be. Later, Miles makes the trip back to Santa Ynez Valley to pursue Maya.

That’s the film in a nutshell.

What we don’t include there is its charm and wit as a movie. It’s a fine film. Like a fine wine! And one to be enjoyed alongside other contemplative modern movies such as Le-Week-End (2013) and The Squid and the Whale (2005).

Sideways has a relaxed pace and heaps on the emotes, with plenty of funny and touching moments between characters.

It’s a film to make you think. Plus, there are a few belly laughs along the way.

But it’s Giamatti’s considered performance (self-loathing and more) that elevates the film towards modern classic status.

Sideways’ Impact on the US Wine Industry

Thanks to the film, Santa Ynez Valley enjoyed a surge in tourism. It’s not difficult to see why really, is it?

That aftereffect isn’t uncommon for a film or TV series. Breaking Bad, for example, led to fans flocking to Albuquerque in New Mexico.

However, it was the impact on the Western US wine industry that’s still being felt to this day. In Sideways, Miles talks up red wine pinot noir but pours scorn on the merlot.

That particular line led to a 2% dip in merlot sales in the Western US. Whilst pinot noir enjoyed a 16% sales boost.

In November 2021, there was even a full study into this published in the Journal of Wine Economics: A “Sideways” Supply Response in California Winegrapes.

“This paper explores growers’ supply response to the 2005 ‘Sideways effect’ demand shock (Cuellar, Karnowsky, and Acosta, 2009) triggered by the 2004 release of the movie Sideways. We use a modified difference-in-difference approach to evaluate the supply response in California and regional supply response differences within California. We use U.S. Department of Agriculture data for the period 1999–2012 and find evidence of a supply response in the post-release period that is consistent with the ‘Sideways effect’ on wine demand. The positive supply response for Pinot Noir is stronger than the negative response for Merlot and concentrated in lower value Central Valley vineyards.”

The paper explains Sideways forced large winemaking businesses to grow more pinot noir grapes across more land. Some of it lower quality.

In time, they then blended the grapes with those grown on high-quality land. Overall, this led to a dip in the quality of pinot noir wines.

If this sort of thing interests you, there’s a full breakdown video of it on YouTube (of course there is) with way more analysis and stats.

On another note, Sideways was adapted from author Rex Pickett’s 2004 eponymous novel. Although the work was only published a month after the film launched.

In 2013, Pickett launched a pinot noir called Le Plus Ultra. And in 2020 he launched another called… Sideways!

You could argue he also RUINED wine in the Western US, but there we go…

The Production of Sideways

Off its $16 million budget Sideways was an unexpected hit, raking in $109.7 million. We remember clearly its release in 2004.

We can’t remember why, but it took us until early 2005 to watch it, when our uni friend Andy bought a DVD copy of it. And four of us young lads, aged around 21, sat and watched the film and enjoyed the bloody thing.

Which is a rather pleasant memory (the magic of movies).

As for the film’s success, word of mouth paid a big part in that. With film buffs telling everyone they knew how great the thing was (a similar thing happened with The Shawshank Redemption in 1994), that launched its potential ever higher.

This was something of a breakout role for Paul Giamatti, who’d been a character actor up to that point. He actually though it was a practical joke when he got the lead part.

Despite having almost no interest in wine and finding all that rather dull, he was able to fake his enthusiasm convincingly in the film.

Thomas Haden Church, interviewed below five years ago, has a great deal of praise for the performance.

Haden Church had retired from film acting by 2004, instead focussing his efforts on voiceover work.  But director Alexander Payne had seen him audition for a role in his 2002 film About Schmidt and wanted him for Sideways.

He was able to convince Haden Church to audition for the role of Jack.

George Clooney had wanted the role and even campaigned for it, but Payne turned him down due to being too famous. But he was later cast in Payne’s 2011 feature The Descendants.

On a final note, the film was a big hit with critics.

It was voted Movie of the Year 2005 in Empire Magazine. It also bagged several Oscar nominations, including for Best Picture and Director. It won out with Best Adapted Screenplay.