The movie starts in a living room and you can tell it’s in a different decade because the furniture and the TV are dated as well as the sound of the TV. A little boy is sitting down, Sidney, watching the TV. The adult Sidney (Simon Pegg) is narrating the beginning about how he loved TV so much he wanted to get in it. He then says he always imagined getting inside the TV as his own promise land. Sidney is then at an awards show at the promise land like he always wanted to be. He’s sitting next to a very famous actress, Sophie Maes (Megan Fox) and says that she told him if she won the award she would have sex with him. The presenter of the award for best actress opens the envelope and it reads Sophie Maes’ name as she reads it into the microphone. You would think Sidney would be happy but he looks otherwise.
He then goes on to tell about how shocked he is to be where he is because a year ago he was in a completely different place. It flashes back to a year ago where he says his magazine was about to go bankrupt. He’s at an awards show in London where all the big English stars are, such as Kate Winslet and Daniel Craig. Sidney has a pig with him and tells the woman at the gate his pig is a celebrity (think ‘Babe’). She says the pig doesn’t have any ID but he convinces her somehow so he can get in. She lets him in but another woman who recognizes him says he can’t come in because she knows he’s a journalist and most celebrities can’t stand them. Sidney then comes up with another plan and checks into a hotel so he can get into an after party. He leaves his pig in his room and he dresses as a waiter and sneaks past the woman who wouldn’t let him in the awards show. In the room during the party things are going well for him. He’s talking to Thandie Newton about how talented and beautiful she is and how he’s a writer. She seems taken with him until his mustache starts falling off and she starts to freak out. At the same time his pig ransacks the hotel room and one of the hotel workers hears all the noise and he opens the door going to see what happened. When he opens the door the pig runs out and gets on the elevator. His pig then gets to the party and starts peeing on one of the patrons’ shoes. She starts screaming asking how the pig got in there. Then the same woman who wouldn’t let Sidney in sees the pig and immediately knows it’s him. She calls security and he runs away. He’s soon about to be surrounded by security and jumps into the pool.
The next day Sidney is working at his magazine. It’s in chaos and everybody is fighting. The phone starts ringing and nobody will answer it. Sidney then says someone needs to answer the phone and they still ignore him while 2 people that work for him keep arguing. The man says he’s going to quit if the woman doesn’t apologize to him. Sidney tells her to apologize because the man owns the copy machine. They then start fighting again and finally another one of Sidney’s colleagues answers the phone. He answers it and it’s Clayton Harding (Jeff Bridges). So Sidney’s colleague thinks because of the huge press fiasco that Sidney caused at the after party Clayton is going to sue them. Sidney then takes the phone and starts talking to Clayton. Clayton says he admires the fact that Sidney was willing to go through so much just to talk to celebrities and he offers him a job with Sharps Magazine a huge celebrity magazine in New York City. He then looks at his employees fighting with each other and asks Clayton to repeat himself again.
Soon Sidney is flying into New York and gets to his apartment. His landlady lets him in and the woman is a bit of a battleaxe. She scolds him as soon as he gets there for trying to make a joke she doesn’t find funny. So then he tells her why he’s there and who he works for. She then says he needs to get some rest for his next big day. He then says he will and soon he’s out partying at a club. He tries to get a dance with many women on the floor and they all dance the other way because he’s such a bad dancer and has no rhythm or moves at all. He soon realizes that he’s all alone and decides to leave. When he leaves all the women go back to where they were and the dance floor is crowded again. He’s outside walking and then sees a woman go into a bar. He turns around to follow her in and he sits at the bar next to her. She asks for a drink and he tells the bartender to make it 2. He tries talking to her and the woman sitting on the other side of him (Kirsten Dunst) at the bar is already irritated by him. She then tells him to move because her boyfriend’s coming soon. He asks the bartender if people are saving seats and he says no. So Sidney won’t move and he tries to go back to talking to the other woman. He then goes by another name or his alias and hands her his business card. The woman snatches it out of his hand and says it’s a library card. The woman he tried to pick up laughs and walks out of the bar. Then the other woman tells him the white Russian he’s sitting in front of is where her boyfriend will be sitting and that he needs to move. Sidney then sees she’s writing in a book and tries to look at it spilling her wine in the book. She gets upset and tells him not to touch it or make it worse. She then gets a phone call and you can tell her boyfriend isn’t going to make it. Disappointed she hangs up and Sidney then picks up that her boyfriend won’t be there. She then leaves while he still tries to apologize. At the same time a regular of the bar named Bobbie (Charlotte Devaney) shows up and takes her seat. They exchange hellos and Sidney attempts to make a move. That same night he brings her home with the music up really loud at his apartment. His door is open and his landlady gets upset hearing everything going on. Bobbie says she’s going to get into something sexier for him while he dances around the living room. His landlady gets there and tells him his music is too loud and his door is open. He says he didn’t know and then Bobbie walks out there with nothing on with a surprise for the both of them. She isn’t quite a woman because a penis is showing and both Sidney and his landlady looked horrified.
The next morning Sidney wakes up to his alarm and a bright sunshine. He then goes to brush his teeth and tells Bobbie to get up because he has to go to work. (I don’t think anything happened since Bobbie is sleeping on the floor. He was just nice enough to let her/him spend the night). He’s on his way dressed very unprofessionally in jeans, tennis shoes, and a t-shirt that says ‘young, dumb, and full of come.’ He then walks into the building and then to the floor where Sharps Magazine is and goes to Clayton’s office. Clayton comments on his shirt as if he disapproves. Sidney hands him one and he takes it and throws it out the window. Sidney tells him how much he adored Clayton’s magazine that he started up a long time ago as soon as he graduated from college. Clayton thanks him and Sidney tries to pitch him some ideas. Clayton tells him not to move so fast because he’s just got his foot in the door and hasn’t even got into the first room. He tells Sidney that he’s going to have to go through a lot to get to the first room and that Clayton is in the seventh room. He tells Sidney that he’s going to be apart of the I Spy department of the magazine and introduces him to this new editor, Lawrence Maddox (Danny Huston). He then looks at some pictures in Lawrence’s office. He sees a picture in black and white asking if the man is Mussolini. Lawrence says no it’s the owner of Sharps Magazine. Sidney then asks who the strange looking boy is in the picture and Lawrence says it’s a girl and the girl is his wife when she was a child. Sidney then shuts up because he’s already screwed up calling the owner Mussolini and the owner’s daughter little Mussolini. Lawrence walks Sidney around familiarizing him with the department and what he’ll be responsible for. He then tells him he’ll be mainly working with Alison Olsen and he sees it’s the same woman at the bar who took his library card. He looks shocked at first but soon doesn’t let it get to him. He then sits at his desk with nothing to do. He looks at Alison and goes to her desk and still looks annoyed to see him there. She tells him to get off her desk and as he does she says hello to another colleague while Sidney tries to use his alias to pick her up. She looks confused but Alison says it’s a name he uses to pick up transvestites. She laughs at him and walks away while embarrassed Sidney says he didn’t know. He then tells Alison that he doesn’t know what to do. She then tells him to caption a photo. Sidney goes back to his desk and calls the number to get the right captioning. A woman answers the phone and he asks her who the man in the photo is. She then says he should know because he’s one of the biggest names in Hollywood. He then calls the man in the picture fat and the woman hangs up. He then calls back and asks if the man with the droopy eye is the man they were both referring to and she hangs up again.
Next Sidney is eating a huge sandwich obnoxiously chewing it. He gets on the elevator and a model gets on. Another model tries to get on but the door closes on her. He then jokes that the elevator wouldn’t let her on because she wasn’t wearing Dolce and Gabbana. The model then says she is wearing Dolce and Gabbana making him look even dumber. She gets off to her floor while Alison happens to step on. She already is annoyed to see him and they start arguing. Soon a woman in all white in sunglasses who looks high profile, steps on and they quiet. Alison tells Sidney not to say anything and he keeps quiet. He then coughs up a piece of his sandwich on her white jacket and tries to remove it. Alison then pulls his hand back so he can’t touch her. They both reach the Sharps floor and she yells at him that she’s the magazine owner’s daughter. He then asks what the big deal is about her and all celebrities. Alison then tells him a million people would kill to get his job and that he’s lucky to be where he is. She then asks how he got hired and he tells her that Clayton called him because he appreciated his snarky magazine showing much distaste for celebrities. He says that Clayton isn’t really all that happy and he sees Sidney in himself or what he used to be a long time ago. Alison says how can he not be happy since he has everything anybody could ever want. Sidney describes Clayton as selling out to get what he wants. He then gets an assignment for later that night and is told to dress the part meaning not the way he’s dressed now.
At his apartment he gets a call from his father and he leaves a message asking Sidney to pick up the phone. Sidney ignores it while getting dressed and leaves. He’s in a limo with Alison and Lawrence. While he’s taking in all the sites of the city, they’re both texting. He asks if they’re texting each other. They brush him off and he begins to look out the window again. They arrive at the party and go to the roof top. Sidney says he’s surprised that everyone treats the journalists with such respect because in London they’re seen as the scum of the Earth. Lawrence tells him it’s different now because he works for a huge magazine. They soon start mingling and introduce him to Eleanor Johnson (Gillian Anderson) who’s a big time publicist that works for Sharps. But for some reason she doesn’t like that title and snaps at Sidney when he calls her that. Soon Lawrence is approached by Rachel Petkoff, an actress. They soon start to chat but he’s soon taken aside by a big time arrogant director, Vincent Lepak (Max Minghella). Rachel tries to tell Lawrence about a new movie she has coming out and that she wants to get it attention but he still brushes her off. Sidney goes to Lawrence telling him it could be a good piece and that he needs to write it as a come back for her since she was big in the 70s. Lawrence says it’s not as big as Vincent and walks away. Sidney finds Rachel and asks her for her autograph. She at first seems hesitant but he names a ton of things she’s been in and she smiles giving it to him. Soon while Lawrence, Alison, and Eleanor are still sucking up to Vincent, Sidney comes to interrupt them asking what’s the greatest film of all time. They all stop so Sidney singles out Alison and she says ‘La Dolce Vita’ but he says no ‘Con-Air’ because of all the elements it has. They all look aggravated and Eleanor mentions her hottest client which happens to be Sophie Maes. She calls Sophie to them and instead of walking around the pool she takes her shoes off and walks across the pool while pulling her hair up so it won’t get wet. Soon the whole party is taken with all eyes on her and cameras flashing all over the place. She gets out and starts talking to the whole group. They soon leave the party while trying to impress Sophie Sidney says her dress gave a good supporting role since she’s an actress. She doesn’t find it funny so he runs out front with her while a ton of paparazzi cameras are photographing her getting into a limo with Lawrence. Sidney gets in but Lawrence makes him get out telling him he isn’t going to the club with them. Lawrence then hands Sophie her dog and they kick Sidney out. He and Alison walk off all the while he suspects that Lawrence is trying to sleep with Sophie and he’s upset because he wants to. Alison says that Lawrence isn’t trying to do anything he’s just dong his job as a journalist.
The next day at work the staff is in a meeting with Clayton. When they finish up Sidney tries to pitch an idea about Paris Hilton being a reclusive person as a joke. It doesn’t go over well with anyone and they all brush him off when the meeting ends. In Clayton’s office, Sidney gets his first assignment. Sidney then goes to interview his first assignment or a singer/actor. He totally screws it up by asking him if he’s Jewish. He then says he doesn’t know how that’s relevant and he replies no. Sidney then asks him if he’s gay. He also doesn’t know how it’s relevant and begins to get upset. He tries to brush it off by talking about his upcoming project but Sidney keeps getting the name of it wrong. He’s later in Clayton’s office with Clayton obviously being upset that he screwed it up. Clayton tells Sidney that he can’t ask those things no matter what angle he’s trying to take. Sidney apologizes and leaves. He walks down the hall and sees the magazine owner’s daughter walking down the hall, the same woman he spit food on. He sees her and freaks out but she tries to step out of his way and falls on the floor. Alison happens to see him and gives him a look as if he shouldn’t help her out. He watches her fall and he walks over her and from Alison’s look he did the right thing.
Sitting at his desk Sidney tries to order a Master card. He’s on the phone with his face taped up and sees Sophie walk in the office with her dog and Eleanor. Of course Lawrence greets them. Sidney hides underneath his desk and Eleanor calls him out. He gets up ripping the tape off his face saying hello. He then tries to talk to Sophie but she is annoyed by him and she says she needs to leave but needs to leave her dog at the office. Lawrence then says to leave it in his office and asks Sidney to get the dog a bowl of water. As he gets it Eleanor tells Sidney he has on a pretty ring. He tells her it belonged to his mother and she comments that it’s sweet. She then asks him if he would like to write a piece on the mega director Vincent Lepak. He asks her why would he want him to do it and she says it would be a good deal for him and a way for him to get closer to Sophie. Alison overhears it and looks at him like she’s cheering him on. He then says he won’t do it since it’s obviously a bribe. Eleanor still asks him to do it but he turns it down. Obviously he hasn’t lost all of what he had when he first left London. Alison is then in the break room eating lunch when her colleague Sidney was trying to hit on earlier and model are looking at clothes on the rack. She asks if she would look fat, even though she can’t be more than a size 2, and Alison tells her no. After they take Sophie’s dog to Lawrence’s office Sidney tries to make friends with it. It first growls at him but he throws a small ball playing fetch and the dog warms up to him. He then throws the ball again but it almost goes out the window and he jumps to close it in enough time preventing the dog from jumping out the window. He falls to the floor relieved but soon isn’t because a statue is unstably wobbling since he hit the cabinet it was standing on. It has a sharp end on it and is about to fall on the dog. Sidney can’t stop it and the statue cuts the dog in half. He then has Alison’s bag and tries to get on the elevator. Alison catches him saying it’s her bag and asks why he has it. Panicking Sidney tells her he needs to borrow it for a minute and she asks why. She then notices a dog paw hanging out the bag and she freaks out because she knows what’s happened. They both run to the window to throw it out but also see Sophie, Lawrence, and Eleanor heading toward them back from lunch. Sidney then throws the bag out the window in a moving scaffold with construction workers on it. Sophie is then flustered looking for her dog and Lawrence asks where the dog is. Alison then looks at Sidney saying she doesn’t know where it is. They walk away looking all over the office for Sophie’s dog. Later Sidney is in Clayton’s office with a story idea about Vincent. He wants to write a story about him but it’s a different angle because it’s more of an insult to Vincent instead of a big feature. Clayton agrees that Vincent is a joke and a little brat and that he’ll let Sidney write it. He then goes home to begin writing his piece on Vincent that’s supposed to be an insult.
They have another meeting with Clayton while Lawrence comes up with a story idea for Sharps. He talks about Rachel Petkoff, the same actress he blew off at the party. He says it would be a good story to write about her since she hasn’t done anything in a while and that her new movie would make a good story. Right after that Clayton promotes Vincent from the I Spy section to editor of another department. Looking shocked, Sidney almost gets up but refrains and goes up to Clayton asking if he got his story on Vincent. Clayton says he did but he wasn’t sold on it. Sidney then leaves and confronts Lawrence about him stealing his story and he tells Sidney to come by and tell him more ideas in his new office. He also tells him to stop flirting with women by the water cooler because it’s creepy and inappropriate. He comments that Lawrence does it all the time but he tells Sidney it’s ok when he does it but not when Sidney does it. This is when you see that Lawrence is a lecherous jerk. That night, Sidney shows up at Sophie Maes’ apartment building. Her assistant comes downstairs and asks what Sidney wants. He asks if Sophie got the present he sent her and the assistant asks if it’s the flowers. He says no he sent her fish because he felt bad about her dog missing (the one he killed). The assistant said yes then asks why he sent them dead. He says he didn’t send them dead since they were alive when he bought them. Feeling stupid he takes the bowl of dead fish to the same bar where he met Alison. Alison laughs when he tells her he buried Sophie’s dog and doesn’t know how the fish died. While at the bar he sees her writing again and asks her what it is. She tells him it’s a book that she’s been working on and wants to get it published. They then hear a TV commercial advertising Sophie’s latest movie as her portraying Mother Teresa. They kind of snicker at it and Sidney says he sees the white Russian sitting there asking about Alison’s boyfriend. She tells him he’s a poet and that he should be there soon. Sidney then seems to be disappointed and then leaves the bar so Alison can be alone with her boyfriend. The next day at his new office, Lawrence is about to sit down with his colleagues when Sidney decides to bring him a present. It’s Bobbie the transvestite from earlier and he has her dance on his lap. Lawrence gets nervous all the while his other colleagues are dancing along and Sidney is taking pictures of him. Bobbie then takes everything off showing her penis. At the same time Eleanor has her two daughters with her and she wants them to meet Lawrence while at the same time he’s getting a lap dance. They all walk in on him and Bobbie turns around with everything hanging out for Eleanor and her two young daughters to see. Soon Sidney is in Clayton’s office saying he didn’t know it was take your daughter to work day and asks why Clayton didn’t like his article on Vincent. Clayton says it wasn’t that great and that he hated the introduction. He then tells Sidney that’s he’s giving him one more freebee or after that it’s over. When he goes back to his desk Alison says she can’t believe he hired Bobbie but he says that Bobbie did it as a favor.
Later it’s 4th of July and everyone’s at a party at Clayton’s Hampton’s town home. Sidney and Alison sit down and talk. Sidney says he doesn’t think any of his stories will get published since he’s sent Clayton 175 stories so far and got nothing. He also doesn’t think his contract will be renewed in a year since he’s been turned down for 4 months. Alison laughs and he asks why she’s been so nice to him since nobody else has. She tells him she feels bad and that he deserves to have someone help him out. He then sees Sophie arrive at the party and runs to say hello. Of course Lawrence is there immediately holding a white Russian calling himself a poet. Sidney then figures out that’s who Alison’s boyfriend is and freaks out running off. He then sees the two talking in the bushes upset the whole time. He’s then approached by a man who first calls himself a spiritual healer but then tells the truth that he’s a dentist. He then asks Sidney if he wants to do some coke. Later while the band is playing Sidney, high on cocaine, stands on top of a ledge and starts singing and yelling at the top of his lungs making a fool out of himself. He then falls on his back and runs off. While running, he finds Alison sitting on the swing crying saying she hates her life. He asks her how could she date Lawrence because of who he’s married to and because he’s such a jerk. She gets upset and kicks him running off. Later at the party Sidney’s lying by the pool when Sophie finds him. She lies next to him and says she needs coke right now because it makes her horny. Excited he finds the dentist that supplied him and runs back to Sophie only to find Alison drunk trying to go home. Instead of giving Sophie the coke and having sex with her he drives Alison home. The whole ride home she cries that she hates the way things turned out and that her career didn’t go in the direction she wanted it to go in. She told him that she planned on moving to New York, getting a job to pay bills, and to write and get published at the same time. But she interned at Sharps and met Lawrence thinking things would work out for her there. She also tells him she broke up with Lawrence and she doesn’t think he cares. Sidney says he does care he just may not know how to show it even though you can tell not even he believes what he’s saying. Soon, so hung over, Alison throws up all over the car.
Sidney carries her upstairs as she shouts she’s a whore and his landlady catches him. If things can’t get any worse his dad happens to step out of his apartment to see what’s going on. Sidney asks him why he didn’t call and he says he did he just never checked his messages. Drunk, Alison asks what Sidney’s dad does and he tells her he’s a writer. He tells her his name is Richard Young and she knows who he is. He’s a famous philosopher who’s written many books and she asks Sidney why he never told her. Sidney’s dad also tells her that Sidney has a master’s in philosophy and this surprises her even more. She gets sick again and goes to the bathroom and goes to bed. Sidney’s dad asks why he hasn’t called him back and you start to see they don’t have the closest relationship. He tells his dad that he knows he doesn’t think he’s good enough but his dad interrupts saying he thinks he is he just doesn’t try hard enough. He says he’s sorry for what his landlady had to see and Sidney tells him it’s better than what he had before which was a hooker with a dick. Richard asks him if Alison is more than a friend and Sidney says no he doesn’t have a chance anyways. Richard tells him he does and that he’s still proud of Sidney anyways. Soon Alison wakes up feeling bad she was so drunk in front of his dad and landlady. Sidney tells her to sit down because he made her breakfast good for a hangover. But she automatically gets sick and runs to the bathroom. When she gets out she tells him she promises to leave after taking a shower. She sees an old picture in his room and asks who’s in it. He says it’s his mother and she asks if his mother is a model. He tells her no she was an actress and was in a few things before she died. She apologizes but he tells her his mother died a long time ago and he was little. TV was a way for him to capture his mother and see what she was about. He then asks about her book and tells her he’ll be happy to edit it and give it some notes if she would like him to. She seems happy that he cares but a little embarrassed by the book. He then gives her a record with the music from ‘La Dolce Vita’ but she says she doesn’t have a record player. He happens to have one so he plays it for her and they dance.
Back at the office, Alison is eating lunch with the same two girls asking about the clothes on the rack. One of them mentions her new boyfriend Sidney but she tells them nothing’s going on. They both laugh and say that’s good since she could do better. At the same time Sidney almost walks into the break room and hears everything. Then the model asks if the dress would make her look fat and Alison tells her no she’s so fucking thin she could snap her like a twig over her leg. They both look at her in shock and she yells at them that Sidney will turn out to be a lot better than anyone at Sharps magazine. They both get quiet but Sidney seems relieved that she stood up for him. He realizes Alison’s getting up so he runs the other way to look as if he weren’t listening in on their conversation. He then pushes the emergency exit door and realizes he set off the alarm. The whole office goes to see him standing there and once again he’s embarrassed in front of everyone. Back at his apartment he’s looking at a poster for a party with a ‘dress like your favorite dead celebrity’ theme. He looks in the mirror and tries to come up with a way to ask Alison out on a date. He puts his teeth in and takes them out to see how it would come across. He dresses up as Dracula and shows up at the party. Tons of costumes are being worn when he arrives. He first sees Vincent and Eleanor together and Sidney comments on Vincent’s costume. He rudely tells him he isn’t wearing a costume so Sidney brushes him off and walks away. He then finds Alison dressed up and is about to tell her how he feels. He tries to ask her out but his teeth make it hard to understand him. Just as he’s about to ask her again, she tells him she has something important she wants him to know and Lawrence walks up giving her a drink. He sees Sidney and walks away when Alison tells him that Lawrence left his wife and now they’re back together. Crushed, Sidney runs off and goes outside when it starts to rain. He goes outside and sees Eleanor and Vincent getting in a limo. He then knocks on the window and tells Eleanor that he’ll write the feature on Vincent so he can obviously get closer to Sophie because his chances with Alison are shot. Vincent tells him to beg and he’ll give him the story. Sidney gets down on his knees but Eleanor and Vincent make the driver take off. In despair Sidney walks home in the rain.
The next day Sidney’s called into Clayton’s office. He tells Sidney that Eleanor wants Sidney to write the feature on Vincent for some odd reason (he must have begged enough last night). He also tells him that Lawrence got fired because Sharps magazine owner didn’t like the idea of him messing around with somebody else while married to his daughter and working at his magazine. Sidney looks content until Clayton tells him Alison also got fired because she was involved with him. He then looks crushed when Clayton tells Sidney he didn’t know how he did it but he’s managed to get himself into the first room. Sidney barely cracks a smile. Clayton also promotes him to Lawrence’s job since he got fired even though it’s only temporary. He then goes to interview Vincent. From that moment everything’s changed for him. He has his own office, he’s getting a lot of complimentary gifts, and he’s moved into a Park Avenue apartment. At a restaurant, Alison is sitting down with her book and an issue of Sharps magazine looking at the editorial line up seeing Sidney’s name and picture as one of the editors. She smiles until Lawrence comes to sit next to her saying he has to run because he’s about to see the hot new talent for a photo shoot. Alison asks how hot is she, knowing he’s probably trying to get in bed with her. He says it’s not that big a deal and leaves when he looks at her book and tells her to stop carrying it around because it’s kind of embarrassing. She gets upset but of course he doesn’t notice and leaves.
Sidney goes to dinner with Eleanor and Sophie when Eleanor announces that Sophie’s up for an Apollo Award for best actress. They toast to that and Eleanor tells Sidney that she enjoyed the profile that he did on Vincent. She then asks him to write one on Sophie if she wins the award. He agrees to it and they toast again. After dinner, they go to a hot club in New York City. Though Simon is amongst powerful people and beautiful women, he doesn’t seem happy because he’s lonely. The next day Sidney gets a knock on the door and answers it to see Alison. He’s happy to see her and she comments on his robe. He tells her it’s Ralph Lauren and she asks who gave it to him. He tells her it’s a complimentary gift from the man himself and then tells her he read her book and gave some notes to help her out. He asks her where she is now and she tells him she’s working for a small literary magazine. When he hands her the papers she looks as if she wants to come in but another woman, the same woman who insulted Sidney at the beginning, walks by and says hello to Alison. She looks disappointed thanks him for the notes and leaves making Sidney feel bad. Soon Simon is in L.A. because Sophie won the award and he’s on a ledge of a hotel room being cheered on by a crowd to climb to the other ledge and walk in on the other balcony in his underwear. He’s scared to death and can’t do it so he comes back in the window. Sophie then challenges him that she can do the same and strips down to only her underwear and is able to climb to the other ledge walking in the other side of the room. They cheer her on and she tells him she wants his ring (his mother’s ring). He says no he won’t give it to her. She then says if he gives her the ring and she wins the award tomorrow night, they can have sex. He gives her the ring in hopes that it will happen. He later goes to his hotel room and is flipping through the channels and sees an old movie. It’s an old movie starring his mother and he starts to feel really guilty that he gave the ring to Sophie for such a shallow reason.
The next night he’s at the awards show in Los Angeles and gets out the limo entering the front and runs into Lawrence. He tells Sidney that he made it into the seventh room as if he’s sucking up to him. Sidney asks how Alison’s doing and he tells her they broke up and she’s left him for another guy. Sidney’s eyes light up until Lawrence tells him it’s not him it’s a guy that goes by Sidney’s alias. While still sucking up Sidney leaves Lawrence feeling even guiltier since Alison still has feelings for him. He’s then in the room where the presenter reads Sophie’s name for best actress and she walks to the stage to accept it. Sidney runs up to her telling her to give the ring back because his mother told him to give it to the woman he loved and that he doesn’t love Sophie. She won’t let him have it back while at the same time Eleanor is running up to him to stop him from taking the ring. Sophie starts fighting him and won’t give it back by pushing him away when he yells that he killed her dog. She gets upset and punches him really hard and choking him at the same time. She then pushes him into a cake while they continue to fight on the floor everybody sees them on TV. Sidney’s dad sees him in his hotel room and smiles while Alison sees him at their usual bar and smiles too. Sidney then sees Vincent and takes his sunglasses and takes them off to stomp on them. Clayton is sitting at another table and laughs when he sees his sunglasses get crushed and then holds it in. Sidney then runs outside trying to leave and a person on the outside lets him out where he symbolically leaves the inside and runs to the airport. When he arrives, he’s on the TV getting beat up by Sophie. The clerk at the desk tells him he can’t get another flight until the next day so he sits in the airport waiting to leave. He also leaves Alison a message telling her he thought he got what he wanted but it wasn’t all that great and he would rather be with her.
He gets back to New York and sees an outside showing of ‘La Dolce Vita.’ He tells the cab to stop and gets out the cab to find Alison with another couple sitting alone. He finds her and they dance together to the song he got her on the record player and they kiss. He then slips his mother’s ring in her pocket and to his horror sees Alison’s book on fire and he jumps to save it.
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