Sidney Young (Simon Pegg) is a small-time, aspiring British journalist who works for a left-wing radical magazine. Following an incident at a party where Sidney accidentally lets a pig loose, he is hired to work for an upscale magazine in New York City. He is hired by Clayton Harding (Jeff Bridges), editor of Sharps magazine, a man Sidney had previously lampooned in his own magazine. The party was thrown by Clayton Harding & it got a lot of publicity because of Sidney's stunt. So, Sidney got plain lucky to land the plum job at Clayton's magazine.Sidney relocates to New York & tries to bed some sexy girls on his first night & fails miserably. He also meets Alison (Kirsten Dunst) at a bar, who is trying to finish her book & fails to make a good impression on her. They end up realizing that they are both colleagues. Sidney annoys the staff he works with, first Alison Olsen (Kirsten Dunst), who is only there to pay the bills whilst she finishes her book, then his boss Lawrence Maddox (Danny Huston). Lawrence is married to Clayton's daughter Elizabeth & Sidney manages to spit a whole piece of ham sandwich on Elizabeth's jacket while she is in the elevator. Alison thinks that Sidney is in a job that thousands would kill for, & he is just not taking it seriously. He openly talks to his boss about going to frat parties & getting drunk in office, which is considered inappropriate behavior at this up-scale magazine.He also dares to target the star clients of power publicist Eleanor Johnson (Gillian Anderson). He then meets new rising star Sophie Maes (Megan Fox); however, he is told by Lawrence not to talk to her. Sidney is smitten by Sophie & wants desperately to impress her & get in her pants. Eleanor approaches Sidney to do a feature on his client Vincent Lepak, who is the up & coming director in NY with a new movie coming out. She wants approval authority on the article, which Sidney refuses to give.Sidney makes it his mission to become something within the business; however, it is almost ruined when he accidentally kills Sophie's dog Cuba, as he was able to stop the dog from going out the window (When Sophie & Cuba are visiting the Sharps magazine office) but unfortunately could not stop a vase from falling onto the dog. Luckily, Alison covers for him and nobody else finds out it was him.Lawrence gets promoted & uses Sidney's ideas to curry favor with Clayton. When Sidney complains, Lawrence threatens him with a sexual harassment lawsuit. In response Sidney hires Lawrence, a stripper in office & proceeds to videotape the whole thing. Unfortunately, that day, Mrs Clayton decides to visit office with Lawrence's daughter's & watches the whole thing with stripper boobs in her sons-in-law face.At a party, Alison and Sidney's relationship grows when she reveals she has just ended an affair with Lawrence. Sidney stops her from driving home drunk, causing him to miss his opportunity to sleep with Sophie (who hooks up with Sidney when he is alone at the poolside & says that she is turned on by his desperate loneliness). At a later party, however, just when Sidney was about to ask her out, it is revealed Lawrence has left his wife and that he and Alison are officially together. In a desperate attempt to up his career, he begs Eleanor to publish a piece on Vincent (Max Minghella), a director he truly hates.The next day at work Clayton reveals that both Alison and Lawrence have left, and he promotes Sidney. Sidney finally becomes successful, getting all the girls that were disgusted by him before and even catching the eye of Sophie. The night before the awards ceremony she stated that if he gave her his late mother's ring and she won best actress, she would have sex with him. Going to the ceremony the next day he sees Lawrence, now being someone, he used to be, stating that he and Alison split as she was in love with him. When the winner is revealed (Sophie), as she is going to get her award, he realizes he does not really love her and asks for his ring back, then, after a heated exchange, he steals back the ring from Sophie, and inadvertently (because of anger) reveals that he killed Cuba. An enraged Sophie attacks him and a huge fight ensues. After the fight, Sidney leaves, quitting his job at Sharps and heading to New York.He meets Alison in the park, where they were showing her favorite movie, La Dolce Vita. She has finished her book and the two finally get together, with him giving her his mother's ring. The movie ends with him accidentally throwing the book onto a candle and jumping for it to stop it from going into flames.