Movies for Men: ‘Sideways’ (2004)

Jack Lopate is about to get married, and all he can think about his cheating on his fiancée.

His buddy Miles Raymond is too buried in his own misery to stop him.

So goes “Sideways,” the Oscar-nominated dramedy that earned five Oscar nominations in 2004, winning for Best Adapted Screenplay (Alexander Payne, Jim Taylor).

The film earned a healthy $71 million stateside, the kind of figure Oscar-bait films rarely earn in our streaming age. Consider three recent examples from this year’s awards season race:

• “Die My Love” – $5.4 million / three weeks 
• “Rental Family” – $3.3 million / opening frame
• “Bugonia” – $16.9 million / five weeks

What’s vital about “Sideways,” beyond its dry wit and assault on Merlot wine? The film captures essential truths about manhood, and some are far from flattering.

Paul Giamatti plays Miles, a school teacher and wannabe author, taking his friend Jack (Thomas Haden Church) on a pre-wedding vacation. The plan is simple – tour Wine Country and celebrate Jack’s final days as a single man.

It’s not so easy.

Jack, a fading actor, intends to leave bachelorhood behind by having sex with someone new before time runs out. Miles is mostly miserable, struggling to find a publisher for his novel and still mourning the loss of his own marriage.

In between wine tastings, the pair flirt with two beguiling women. Sandra Oh plays Stephanie, a plucky bartender who falls for Jack’s screen-tested charisma. Virginia Madsen, snagging a Best Supporting Actress nomination, is a budding wine snob enchanted by Miles’ expertise on the subject.

What could go wrong? Plenty in this wise and witty film that holds up perfectly 21 years later.

Director/co-writer Payne ensures every exchange is grounded in real emotions. Miles is a sad sack, but he’s relentlessly loyal to Jack. The would-be groom feels the same toward Miles, putting up with endless shrugs and moods.

Their bickering feels natural, not forced. And it’s often very funny.

Watching the pair woo the ladies in question is a fascinating study in contrasts. Jack could charm Stephanie in his REM sleep. Miles misses every cue Madsen’s Maya throws his way, turning their flirtation into a master class in cringe.

Why is this a “men’s” movie? Where are the car chases and machine gun shootouts?

Payne and co. capture how men think, behave and respond to pressure. Miles should counsel Jack against pursuing one last fling, but he can barely keep his head up in his sorry state.

Jack has a seemingly sweet fiancée whose family can set him up for life in the family business. That isn’t enough for someone able to woo women at a moment’s notice. He sees marriage as the end of his libido, and it terrifies him.

What if I meet someone better? Younger? More beautiful?

Both understand that Miles’ best chance at romance, on a superficial level, is to pretend his book deal is a done deal. They underestimate how Maya might react to the book itself, or that she finds Miles’ intellect as attractive as six-pack abs.

The men in play are immature, reckless and occasionally rude, yet the script also views them with empathy. Plus, the consequences for Jack’s behavior flow organically from the story.

There’s no speech about The Patriarchy to slow down the story or betray the redemptive arcs.

FAST FACT: They called it the “Sideways Effect.” Sales for Pinot Noir spiked after the film’s release, based on Miles’ affection for the varietal. The news wasn’t as good for Merlot, which suffered a sales slump due to Miles’ distaste for it.

The best movies about men and male friendship acknowledge flaws without condemning the characters. Yes, Jack takes a whupping once Stephanie realises he’s mere days from getting married. And Miles’ best chance at romance nearly capsizes after Maya learns how his pal betrayed Stephanie.

Consequences, not finger-wagging lectures. Ah, to be back in 2004 again.

Payne’s camera captures the various vineyards and thoroughfares with an eye for their unassailable beauty. He also highlights the seedier side of the duo’s actions.

The sad hotel hot tubs. The lonely walks along neon-lit streets. The motel rooms and their ghastly bedspreads.

It’s like … life, and “Sideways” never flinches from it. Even when we see men at their very worst.

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