Jack: She must be married or something. beep came in while I was beep his wife in the ass.
Miles: So you walked home? Jesus Jackson that must be 5 clicks.
Jack: I ran. I think I rolled my ankle too. I cut through and ostrich farm. Those beep are mean.

Jack: What's wrong with her? I should sue her ass. The only reason I won't is to protect Kristine.
Jack: How did they know the weekend was next weekend?
Miles: I don't know maybe the guy from the post heard us talking about it.
Jack: I don't know, it sure seems fishy.

When Jack and Miles are walking off of the golf course and Jack says "don't you want to feel that cozy little box grip down on your Johnson?" and the guy and his son look disgusted.

That's a great one

That scene cracked me up when I first saw the trailer. When the followup instruction to "spit out out" wasn't in the finished film, I was slightly disappointed as I thought that was perfect for the scene to better define the characters, one character, Miles, a connoisseur of wine (and also a drunk) and the other character, Jack, an uncultured buffoon who has no experience (or real interest) in wine tasting but does it to appease his friend in the hopes of his friend reciprocating in appeasing him with having some promiscuous fun with the locals before he settles down into marriage. It's a stark contrast in characters. You could say they are "the odd couple" as they aren't alike in any way but remained friends through college anyway. It's one of my all-time favorite movies. I've seen it many times. The scene where Jack goes back to the hotel naked is one of my favorites too as it begins as a funny story of what happened to Jack and devolves into Jack begging Miles to help him for fear that he will lose his fiance because of his foolish promiscuity. It's a crime that SIDEWAYS didn't win an acting award as there was some excellent acting in that film, especially the fearless performance by Thomas Haden Church. He and Giamatti were robbed by MILLION DOLLAR BABY, the film as a whole was actually, as it won the major categories that SIDEWAYS was also nominated in (and yes, it was a crime that Eastwood got an acting nod over Giamatti).

Bingo! My favorite line from the movie, hands down.

I know it's basically a throwaway line, but "Are you chewing gum?" always makes me laugh.

It won Adapted Screenplay not Original as it was adapted from the novel by Rex Pickett.

Yeah, I rarely buy DVDs of movies since you can rent them anytime you want, but I did purchase this one for my small collection. Almost gets better the more you watch it. Two very sleazy types you wouldn't want to know in person, but somehow they're fascinating.

It certainly did win the Oscar for Original Screenplay. Alexander Payne is a genius, his other films are fantastic too.
Sideways, after having seen it another time, i now consider one of my favorite films of all time
Favorite films of all time list
http://www.imdb.com/list/ls031708001

That was a great one! I remember Roger Ebert laughing about it in his review. (I miss Roger.) Also memorable to me was when Jack and Miles are parked outside the house where Jack left his wallet. Jack says Miles needs to be the one to go in and get it. When Miles starts to protest Jack says, "do I have to do EVERYthing??" HA HA HA - like he ever sticks his neck out for anything!
Such a great script. Didn't it win the Oscar?

Lol. I agree, the way Giamatti delivers that line is gold.