Although it’s a Hollywood comedy about a couple of guys going on a trip for a bachelor party, Sideways is about as far removed from The Hangover as it could possibly be. As the characters take a trip through wine country, there’s an extra degree of sophistication to the bachelor party, and as the groom-to-be falls for another woman, there’s also an added layer of depravity to the proceedings.

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Alexander Payne made a film about imperfect characters reveling in their flaws. Here are five scenes from the movie that made us laugh out loud, and five that made us feel something.

Laugh Out Loud: Miles Accidentally Reveals Jack Is Getting Married

Just when things are going well for Miles and Maya, he screws it all up by accidentally letting it slip that Jack is getting married. It’s the day after they slept together for the first time and they’ve just spent a wonderful morning going around town.

When he makes this accidental revelation, Maya is understandably disgusted by the dishonesty of both Jack and Miles, and breaks things off with Miles on the spot. The look on Miles’ face as he realizes he’s screwed up is priceless.

Hit Us In The Feels: Miles And Maya Discuss Wine

Miles holding a wine glass in Sideways

When you meet someone really special, you feel the connection immediately. And that connection can be seen in Miles and Maya’s first one-on-one conversation in Stephanie’s wine room.

As Stephanie and Jack go to the bedroom to have sex, Stephanie tells Miles and Maya to take whatever wine they want. The two have an in-depth discussion about wine ⁠— more in-depth than they have with their friends ⁠— and they really connect over a mutual passion.

Laugh Out Loud: “I Am Not Drinking Any F****** Merlot!”

Miles screams about Merlot

Miles’ passionate hatred of Merlot made a huge dent in the Merlot industry. When Jack forces Miles to come on a double date with him and it’s suggested that he might have to drink some merlot, he says, “If anyone orders Merlot, I’m leaving. I am not drinking any f**king Merlot!”

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After Sideways came out, merlot sales dropped by 2%. According to a 2014 study by Vineyard Financial Associates, Miles’ critique of merlot in Sideways cost merlot farmers a whopping $400 million.

Hit Us In The Feels: The Publisher Rejects Miles’ Manuscript

Throughout Sideways, Miles is holding out hope as his manuscript is in the hands of a publishing house that could make his dreams come true. When he receives a call from his literary agent, he steps outside, hoping for good news.

However, his agent tells him that the publisher is passing on his book, leaving him without a hope in the world.

Laugh Out Loud: Miles Drinks From The Spit Bucket

When Miles finds out his novel has been rejected by yet another publisher, he understandably feels pretty bummed out. So, he goes back into the wine tasting and asks the server to pour him more than a sip of wine. The server refuses, because he’s only supposed to give him enough to taste it.

So, Miles grabs the bucket that all the patrons have been spitting wine into all day and starts pouring it down his throat. Jack has to jump in to defuse the situation and get Miles out of there.

Hit Us In The Feels: Miles Drunkenly Calls His Ex-Wife

Miles from Sideways

Midway through Jack and Miles’ double date, when Miles has had a few too many glasses of wine and learns from Jack that his ex-wife Victoria has remarried, he excuses himself to use the bathroom. But instead of using the bathroom, he goes to the phone and drunkenly calls Victoria.

Paul Giamatti did a powerful job of playing Miles’ depression in this movie, and as deserved as Thomas Haden Church and Virginia Madsen’s Oscar nods were, he was definitely snubbed for a nomination. When he comes back to the table, Jack looks at Miles suspiciously and says, “Did you drink and dial?”

Laugh Out Loud: A Naked Angry Husband Chases Miles Out Of His House

In the middle of the night, Miles is woken by a banging on the door. It’s Jack, completely nude, and he’s just run all the way back to the motel from the home of a woman he was sleeping with when her husband came home.

Jack makes Miles drive him back to the house and sneak in to grab his wallet. He finds the wife and husband having sex in the bedroom, then spots the wallet. He runs in, grabs the wallet, and gets chased out of the house by the naked husband.

Hit Us In The Feels: Victoria Tells Miles She’s Pregnant

After Jack’s wedding ceremony, Miles bumps into his ex-wife, Victoria, who tells him that she’s pregnant. Depressed by this, he forgoes the reception and instead drives to a fast food restaurant, where he eats alone.

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He pours his prized wine, a 1961 Château Cheval Blanc, into a disposable soda cup and starts knocking it back. All the meaning he attached to that wine is gone, and he just wants to drink it and get it over with.

Laugh Out Loud: Jack Crashes Miles’ Saab

When Jack’s lover, Stephanie, found out he was getting married, she attacked him with her motorcycle helmet. So, he has to think of a way to explain away his injuries to his bride-to-be.

On the drive home, Jack suddenly swerves Miles’ Saab 900 convertible off the road and heads for a nearby tree. Miles begs him not to crash the car, but he crashes it, prompting Miles to cry out, “What the f*ck!” The crash doesn’t do enough damage to the car, so they put a cinder block on the gas pedal and send it speeding into a ditch.

Hit Us In The Feels: Miles Returns To Wine Country And Knocks On Maya’s Door

After Jack’s wedding, Miles returns to his regular routine. He continues his teaching career, he finds a kind of status quo in being single and unpublished, and then he gets a voicemail from Maya. She says she’s read his manuscript and invites him to come back and see her.

The movie ends with Miles driving back up to wine country and knocking on Maya’s door. It’s a delightfully ambiguous note to end the movie on. Maybe Miles and Maya lived happily ever after. Maybe things will crash and burn like his first marriage. Who knows?

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