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.
Hey! Never saw it: on today’s agenda. (snowy, cold, slippery outside: nice fire inside.
I had forgotten how much I love this movie. I own it on dvd. I think I’ll dust it off today and watch.
Loved this movie! It’s funny and real, the performances were fantastic and I saw a talent level from Virginia Madsen that I hadn’t seen before. Not all of us are Marvel-addicts and hyper-Christian bullies, highly recommend one watch and decide for themself.
Yeah, uh……..no. This movie sucked. I can easily think of a dozen other films that meet the author’s premise far better.
You are clearly high AF. Happy Turkey Day.
Yes! I love this film. Of course, I sent most 20s like Miles–an oft-depressed wannabe writer who couldn’t catch a clue if it hit me in the face. Well written, beautifully shot, and brilliantly acted. The Rex Pickett novel is really good as well.
This movie was hilarious! And for anyone dogging it because the characters are imperfect and doing imperfect things, it’s called the suspension of disbelief… try it out. This movie is not meant to be a church sermon or a political rally. Its a character study with 4 completely different, yet similar personalities. The fact that the acting is outstanding is the icing. And for the record, Pinot Noir is superior to Merlot 😉
this movie is so bad that my family hand my dad’s copy all over the family as a joke because everybody hates that movie and does not even want it in their house. it was a movie probably made by snobs for snobs and doc Kenny guess which one you are. lol
I’m not a snob and thought it was hilarious. No need to make it personal there, guy.
I was able to fully enjoy the movie without feeling it was speaking about men in general, or me specifically. Funny part is that, as Mr. Toto notes, the male leads are unlikable – one a self-seeking, immature cad, and the other a self-pitying jerk (recall the scene where he sneaks into his mother’s house to steal cash in order to fund his trip). The movie worked for me because they weren’t caricatures. I know men like this, and I’ll even cop to having a bit of Miles in me. Again, I did not feel preached to. Being a bit of a wine snob, having some familiarity with the filming locations, and the performances of everyone in the cast all combined for a thoroughly enjoyable experience that I would gladly repeat.
If you want to watch a really good Thomas Haden Church movie (it’s actually a two part TV mini-series) watch Broken Trail with Robert Duval.
Oh LORD no; this movie is terrible, for men or women. It doesn’t say anything about men; it says something about these two particular characters, terrible losers who still manage to trick women into sleeping with them. It’s a sad movie with a nihilistic view of manhood. You might as well tell me why American Beauty was “a masterpiece examination of modern man.” That’s no more ridiculous than giving such props to Sideways.
I agree with you and to a lesser extent Christian.
This film does not have any of the usual woke/patriarchy/LGBT messaging that is pervasive in today’s media. If it were made today you can be sure one of the characters would be gay.
This fully embraces what used to pass for Hollywood liberalism – men were selfish cads – sleeping around is okay – very much the secular free love, do it if it feels good mindset.
What this film lacks are any conservative values – yes they are friends – but I hope I am a better friend and support to my friends than these two. It is very much (as Christian notes) a film about how we are broken and failing, not about how we should be.
I see plenty of broken people all around me. I didn’t find the humor here like many others have. If we all liked the same things life would be boring, but this isn’t a film I have recommended.
Happy Thanksgiving.