Alternate Title: Grapes of Wrath
Miles (Paul Giamatti) decides to accompany his best friend – possibly his only friend – Jack (Thomas Haden Church) to Wine Country for a week as a sendoff before Jack gets married. Miles is just about the mopiest guy on the planet while Jack is hard to rile. Jack is determined to get laid before he gets hitched, but Miles has a hard time relaxing as he waits for news of his pending book publication. However, Miles does manage to use every chance he gets to educate Jack about wine.
When Jack discovers that Miles actually likes a local waitress named Maya (Virginia Madsen), he becomes almost more invested in getting Miles laid than himself. That changes as soon as Jack meets Stephanie (Sandra Oh). As Jack gets closer with Stephanie, Miles walks around like a human storm cloud, fretting that the week “was supposed” to go differently than it is going. In fact, the only time Miles seems to not be grumbling is whenever Maya is in the room.
Sideways is the classic frat boy buddy comedy if the frat boys never left the frat and switched from Coors Light to grown-up grape juice. It’s clear that Jack and Miles are both selfish scumbags, but for whatever reason, they’re endearing all the same. It’s like taking a sip of wine that doesn’t taste all that great, but you and your best friend still manage to polish off the whole bottle together (and open a second one). Bitter at first, Sideways hits plenty of genuinely sweet notes.
Now it’s Your Turn…
Sideways was nominated for Best Picture in 2004, but did the Academy get it right?