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NOTE: This spoiler was submitted by Jeremy
1930's, Hollywood - Phil Stern (Steve Carell) is one of the most successful agents in the business. He's at a party when he receives an important phone call, believing it to be Ginger Rogers seeking new representation. It's really Phil's sister Rose Dorfman (Jeannie Berlin), telling Phil that her son is going to move over to Los Angeles to find a job working with him.
Bobby Dorfman (Jesse Eisenberg) lives with his mother Rose and father Marty (Ken Stott), a jeweler. He has two other siblings; schoolteacher Evelyn (Sari Lennick), who is married to Leonard (Stephen Kunken) with a daughter, and gangster Ben (Corey Stoll). Ben is infamous for murdering numerous people around town with whom he's gotten into dirty business with.
Bobby makes his move to Hollywood and tries to meet with Phil at his office, but is told to wait for hours until his secretary says Phil is too busy, and for Bobby to try again on Friday. Bobby goes back, only to find out that Phil took his wife to Mexico.
At night, Bobby calls for a woman to be sent to his apartment. The woman, Candy (Anna Camp), is on her first job, and she got Bobby's room number wrong. He chastises her for screwing up and doesn't even want to have sex with her anymore because he is too tired. Bobby hands Candy the money and tells her to leave, but she starts crying. Bobby reluctantly says he'll have sex with her until he gets fed up with the argument and just sends her out the door.
Bobby finally gets to sit down and meet with Phil to discuss having a job. Phil agrees, then has another secretary of his, Vonnie (Kristen Stewart), take Bobby around town and show him the area. Vonnie drives Bobby around to see the homes of some celebrities, including Joan Crawford's house. Bobby is smitten with Vonnie for her down-to-earth personality as he gets to know her during their time together. When he asks her out on a proper date, she tells him she is seeing a journalist named Doug.
Bobby gets promoted to look over scripts. He gets to attend parties with Phil and meets other people in the business. Bobby still tries to get close to Vonnie, despite her relationship.
Turns out that "Doug" is really Phil, and he is having an affair with Vonnie behind his wife's back. Although she doesn't want to be the cause of a failed marriage, she is also in love with Phil. Eventually, however, Phil says he can't continue the affair and he calls it quits with Vonnie. She tearfully goes to Bobby's apartment later on for comfort.
Bobby and Vonnie begin dating and are genuinely in love, but Phil becomes miserable without Vonnie. He tells Bobby about his mistress without saying who it is. Phil soon learns that Bobby is with Vonnie, which upsets him even more.
Phil approaches Vonnie at her other job where she takes people's coats at a venue. He is preparing to tell his wife about their affair, but he asks Vonnie to marry him. He heads off and returns to his office where Bobby finds him. Phil mentions a signed letter and photo from Rudolph Valentino on his desk, which Bobby knows came from Vonnie. He goes to see her at her job and asks her if she will choose him or Phil. Vonnie says she chooses Phil.
Bobby returns to New York and begins to run a nightclub with Ben after he and his buddies killed the previous owner and buried him under cement. Bobby is soon swept up in the world of cafe society, getting to know more rich folks and celebrities, as well as politicians and gangsters. Here, Bobby meets the woman that would eventually become his wife, Veronica Hayes (Blake Lively). She is recently divorced after her husband cheated on her with her best friend. Bobby and Veronica date, and she becomes pregnant, leading them to get married at city hall. At one point, he accidentally calls her Vonnie (since Vonnie's full name is also Veronica).
Evelyn and Leonard have issues with their neighbor Joe (Brendan Burke), a very nasty individual that constantly causes distress to the couple. Apparently, Joe has threatened to shoot Evelyn's dog, and since she knows he's a security guard, she figures he most likely has a gun that he's ready to use. Fearing for the safety of her and her family, Evelyn asks Ben to have a talk with Joe. Ben and his pals kidnap Joe, shoot him, then bury him under cement as well.
Bobby is taken by surprise when Phil and Vonnie, now married, visit New York and attend the nightclub. Bobby and Vonnie agree to go around the city. They spend a day together, eventually kissing on a bridge at the park.
After Leonard gets suspicious over what happened to Joe, Ben is eventually caught and tried for murder. The evidence against him, in addition to his other multiple crimes, is enough to get him the death sentence. While in prison, Ben becomes a Born Again Christian, which upsets both of his traditionally Jewish parents. Ben later gets the electric chair, and he is cremated. Bobby spreads his ashes near one of Ben's favorite spots.
Following Ben's death, the nightclub gains more patrons for his notoriety. Bobby travels to Los Angeles to consider opening up a club there. He spends time with Vonnie while there, where she mentions that she and Phil will visit New York again. She and Bobby decide it's best if they don't see each other again.
Upon his return, Veronica asks Bobby if he cheated on her since she had a dream about it. He says dreams are just dreams, and he kisses her forehead.
It's New Year's Eve. Bobby is celebrating at his club while Vonnie and Phil are at a Hollywood party. As the people start counting down to midnight, we see both Bobby and Vonnie in their own locations both looking rather sad and regretful.
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Bobby Dorfman moves to Hollywood to get a job working with his uncle Phil Stern, a powerful agent. Bobby falls in love with Phil's secretary Vonnie, who is already engaging in an affair with Phil. Despite falling for Bobby, Vonnie ultimately chooses to marry Phil.
Bobby returns to New York and opens a nightclub with his gangster brother Ben. Bobby marries a woman named Veronica and has a daughter with her. Vonnie and Phil appear in New York, briefly rekindling the spark between her and Bobby, but they choose to go on with their proper relationships. In the end, it appears they both regret choosing other people.
A subplot involves Ben's gangster life and his murder of his sister's nasty neighbor. He is found guilty and sentenced to the electric chair.