25 Sideways Quotes From the Popular Comedy Drama Movie

Enjoy these Sideways quotes from the award-winning comedy-drama movie.

Sideways was released in 2004 and is based on Rex Pickett’s 2004 novel, also named Sideways.

The plot of the movie follows middle-aged, long-time friends Miles and Jack.

Jack is about to be married, and Miles is depressed with his life, so they decide to go on one last adventure before the wedding and go to wine country in the Santa Ynez Valley.

The movie was directed by Alexander Payne and stars actors and actresses Paul Giamatti, Thomas Haden Church, Sandra Oh, and Virginia Madsen, among others.

Upon release, the movie received positive reviews from critics and won multiple awards.

The movie was also a hit at the box office, where it grossed over $109 million against a $16 million budget.

Take a look at these Sideways quotes to learn more about the movie.

The Best-Known Sideways Quotes

Here are some of the best-known quotes from the movie.

1. “You gotta help me! You gotta help me!” — Jack

2. “I might be in love with another woman.” — Jack

3. “If they want to drink Merlot, we’re drinking Merlot.” — Jack

4. “Half my life is over, and I have nothing to show for it.” — Miles

5. “All I have is my instinct. You’re asking me to go against it.” — Jack

6. “The day you open a ‘61 Cheval Blanc, that’s the special occasion.” — Maya

7. “Really? 24 hours with some wine-pourer chick, and you’re fu..ing in love?” — Miles

8. “A bottle of wine is like life itself: it grows up, evolves, and gains complexity.” — Maya

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9. “Despite your crass behavior, I’m actually glad we’re getting this time together.” — Miles

10. “Cammi gets off in an hour, so I was thinking I’d just hang around and have a drink and make sure she gets home safe.” — Jack

Sarcastic Sideways Quotes

Here are some sarcastic quotes from the movie.

11. “Mies, did you drink and dial?” — Jack

12. “Are you still seeing that shrink?” — Jack

13. “Now the cards are on the table.” — Miles

14. “You’re such a fu**ing loser. You make me sick.” — Miles

15. “I’m trying to get you laid, I’d appreciate a little help!” — Jack

16. “That is beautiful. ‘A smudge of excrement… surging out to sea.’” — Jack

17. “That’s going to be my best man gift to you this week. I’m going to get you laid.” — Jack

Sideways Quotes That Are Remembered By Fans of the Movie

Every fan of the movie is sure to remember these quotes.

18. “ I need to be spanked!” — Stephanie

19. “You’re getting married?” — Stephanie

20. “You’re crazy. You’ve gone crazy.” — Miles

21. “Speak for yourself. I get chicks lookin’ at me all the time.” — Jack

22. “You’re an infant, Jack. This is all a big party for you… but not for me.” — Miles

23. “Here’s what I’m thinking: you and me, we move up here, we buy a vineyard.” — Jack

24. “No, if anyone orders Merlot, I’m leaving. I am NOT drinking any fu..ing Merlot!” — Miles

25. “I’m not a writer, I’m a middle school English teacher. Well, the world doesn’t give a shit what I have to say.” — Miles

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What Happens to Miles and Jack?

On the way to their vacation, Miles stops and steals money from his elderly mother so that he can enjoy the vacation.

Once they arrive, to Miles’ dismay, Jack decides to cheat on his fiancee and sleeps with multiple women.

Miles falls in love with a woman, and after initial turmoil, the movie ends with Miles returning to her house to reconcile.

Tell us your favorite Sideways quote in the comment section!

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