邁爾斯（保羅•吉亞瑪提 Paul Giamatti 飾）和傑克（湯瑪斯•哈登•丘奇 Thomas Haden Church 飾）是老朋友了，看著傑克即將踏入婚姻殿堂，邁爾斯更加感歎起自己失敗的生活：婚姻失敗、作家夢遙不可及、幹著無聊枯燥的職業、不再年輕的歲數。邁爾斯對葡萄酒的研究頗為深厚，於是兩個人決定前往加州的葡萄酒生產基地狂歡一次，如果遇上一夜情當然是最好不過了。
Sideways is a 2004 Academy Award-winning and Golden Globe Award-winning comedy/drama film, co-written and directed by Alexander Payne. It is based on the 2004 novel of the same name by Rex Pickett.
Miles (Paul Giamatti) is a single divorcé, unpublished writer, eighth-grade English teacher, depression sufferer, and xenophile, who takes his soon-to-be-married actor friend and old college roommate, Jack (Thomas Haden Church), on a week-long road trip through Santa Ynez Valley wine country. Miles wants to drink wine, eat great food, play golf, enjoy the scenery, and send Jack off in style. However, Jack is more interested in "sowing his wild oats" and having one last sexually libertine week. Soon after their arrival in wine country, they meet Maya (Virginia Madsen), a waitress at Miles' favorite restaurant, and Stephanie (Sandra Oh), a winery employee who happens to be friends with Maya.
Neither tells the women about Jack's impending nuptials the next weekend. Jack soon finds himself in a sexual and romantic imbroglio with Stephanie, which inevitably puts an abrupt end to Miles' plan for taking Jack out for a good time. Although more than a little reluctant, Miles is willing to entertain Jack's antics, convinced of the temporary nature of his newfound relationship with Stephanie. Miles' decision to indulge Jack's philandering ways is also influenced by his decision, with Jack's strong encouragement, to begin to act on the crush he's developed on Maya. Soon, Jack's relationship with Stephanie accelerates, putting Miles in a precarious predicament as he continues to court Maya casually.
Eventually, Miles consummates his relationship with Maya. The next day, he lets slip the upcoming rehearsal dinner, which leads to his revelation of the upcoming wedding. An infuriated Maya, in turn, breaks the news to Stephanie, who becomes apoplectic and mercilessly attacks Jack, smashing his nose with her motorcycle helmet, which requires him to get medical treatment at a hospital. Miles and Jack later have a tense conversation where Miles flatly denies that he ever said anything about Jack's engagement to Maya.
Miles hopes that this is the end of Jack's behavior as they settle down to a barbecue dinner. Undaunted, Jack spots Cammi, a heavy-set waitress, who recognizes Jack and whom he dubs 'two tons of fun'. He goes home with her, leaving an irritated Miles once again to his own devices. Back at the hotel, Miles is awakened in the middle of the night by a naked Jack, who confesses that a cuckolded husband arrived home from work and caught Jack in flagrante delicto with his wife, and he was forced to escape in the nude and run "five klicks" (3 miles) back to the motel. A distraught Jack reveals that unfortunately, he has left his wallet behind, which contained custom-designed wedding bands. He desperately wants to retrieve his belongings, but needs Miles' help. Initially, Miles laughs at the situation and refuses to help Jack, as he believes the incorrigible skirt-chaser may finally have learned a lesson. However, Miles sees the desperation in his friend's breakdown, and agrees to help him by driving him back to Cammi's house. After Jack pleads he's in no fit state, Miles reluctantly agrees to personally reclaim the wallet by sneaking into the garbage-strewn dwelling to retrieve it, passing by the Rubenesque couple, who are now engaged in sex themselves. He retrieves the wallet, but is spotted and is chased down the street by the enraged, portly, naked husband. Miles hops in his car and barely makes a clean getaway.
On the way back to Los Angeles, where the wedding is being held, Jack runs Miles' red Saab 900 convertible into a tree and then into a ditch, in order to have corroborating evidence for his story that a car accident mangled his face. The ploy works, much to Miles' chagrin. Jack's fiancee sympathizes with his injuries.
Miles' ex-wife Victoria is still friendly with Jack, and is at the wedding. During the road trip, Jack had revealed that Victoria remarried, but his romantic feelings for her are still strong. At the ceremony, Victoria introduces Miles to her new husband and also informs Miles that she is pregnant. Miles does his best to contain his deep sadness and congratulates her, but abruptly decides to skip the wedding reception and instead return to his dingy apartment in San Diego, where he fetches his prized bottle of wine, a 1961 Château Cheval Blanc, and drinks it from a plastic cup at a fast-food restaurant.
It seems that this is the end for Miles, but Maya eventually returns his apologetic phone call. She has read his unpublished manuscript, and a letter of apology that he sent to her. Touched by his sentimental side, she leaves a message on his machine telling him that she cannot believe the book was turned down, as she admires it, but is also confounded by portions of it; in particular, the ending. Her message also discloses portions of his novel that, in turn, reveal events in Miles' life that may have shaped his bleak perspective on the world, particularly the implication that his father might have committed suicide (although this is unclear as, according to Miles, the novel is only loosely based on events in his own life). The film ends with Miles again driving north, standing on Maya's doorstep, and knocking on her door.
Jack: Somebody finally arrived. You finally got here. Mr. Prompt.
Mrs Erganian: Oh, remember my kids? Alex, Helen?
Miles: Hi. How areyou?
Mr Erganian: We were thinking maybe you went the wrong way, you went to Tijuana…
Mr Erganian: And they don't let you back.
Miles: Yes! Yes! I had to bribe them.
Chiristine: Hey, Miles.
Miles: Hey. How are you, Christine? Yeah, the freeway was unbelievable. Unbelievable. It was bumper-to-bumper the whole way. People getting an early start on the weekend, I guess. Granted, I got a late start, but--
Chiristine: Well, we're just glad you made it.
Mrs. Erganian: Christine, why don't you ask Miles about the cake?
Christine: Oh, good idea. Come with me.
Miles: What's this?
Jack: We don't really have time for that, 'cause we gotta hit the road.
Christine: Oh, come on!It's just gonna take a second!
Mrs. Erganian: Yeah. Jack tells us you are publishing a book. Congratulations.
Mr Erganian: Yes, congratulations.
Miles: Yes, well, uh, it's not exactly finalized yet. So-- There has been some interest, and—
Mrs. Erganian: Your friend is modest.
Jack: Oh, come on, Miles. Don't be so modest. Indulge them. Don't make me out to be a liar.
Mr Erganian: What is the subject of your book? Nonfiction?
Miles: Uh,no. It's-- It's a novel. Fiction.
Mr Erganian: Yes.
Miles: Oh. Although there is quite a bit from my own life, so I suppose that, technically, some of it is nonfiction.
Mr Erganian: Good. I like nonfiction. There is so much to know about this world. I think you read something somebody just invented it, waste of time.
Miles: That's an interesting perspective.
Chiristine: So, which one do you like better?
Miles: Oh, well, I like them both. But, um, if pressed, I would have to say that I prefer the dark.
Jack: Told ya! Bye-bye.
Mr Erganian: Bye.
Jack: Bye. Where the fuck were you, man? Huh? I was dying in there. We're supposed to be a hundred miles away by now.
Miles: I can't help the traffic.
Jack: Oh, come on. You're fucking hungover. You know you are.
Miles: Okay, there was a tasting last night, yes. But I wanted to get us something nice for the ride up. Check out the box. Why did you tell them that my novel was being published?
Jack: 'Cause you said you had it all lined up.
Miles: No, I didn't. No. No. What I said was that there was some interest at Conundrum.
Jack: Yeah. Conundrum.
Miles: And that one of the editors was passing it up to a senior editor.
Jack: Sounds pretty good to me. Sounds like you're in.
Miles: No. It's a long shot. Besides, Conundrum, it's just a small specialty press. Anyway, I'm not gonna get my hopes up. You know? I've stopped caring. The hell with it. I have stopped caring.
Jack: It sounds like it's gonna happen this time. I mean, I can feel it.
1. Mr. Prompt.
這是一個開玩笑的說法，prompt 有“敏捷的，迅速的，及時的”意思，這裡Jack 用來諷刺Miles，因為他很晚才到。
2. It was bumper-to-bumper the whole way.
Bumper-to-bumper 指“（汽車）擁塞的，擁擠的”，自然也就是交通擁堵了，比如： bumper-to-bumper traffic 擁塞的交通。
3. hit the road
意思是“開車上路”，例如：Come on, it's time to hit the road. 快點，該上路了。
4. It's just gonna take a second!
表示“只要很短的時間”，a second 極言時間之少，是誇張的說法。
5. if pressed
6. Told ya
Ya 是 you的一種口語形式。
7. I can't help the traffic.
8. line up
這裡的意思是“organize, make ready, make the arrangements for組織好，準備好，安排好”，比如：They lined up considerable support for the bill. 他們召集了很多人支持這個提案。
9. get one's hopes up
Don't get someone's hopes up是一個習慣用語，當你委婉地拒絕別人，不想讓別人期望太高的時候，就可以用到這句話。比如：---How did your finals go? 期末考試的結果如何？---It went well, but I don't want to get my hopes up. 還不錯，不過我不會寄太多希望。