Marty Faranan (Farrell) is a struggling writer in Los Angeles, California who dreams of finishing his screenplay, Seven Psychopaths. Marty's best friend, Billy Bickle (Rockwell), is an unemployed actor who makes a living by kidnapping dogs and collecting the owners' cash rewards for their safe return. His partner-in-crime is Hans Kieslowski (Walken), a religious man with a cancer-stricken wife, Myra. Billy helps Marty with Seven Psychopaths, suggesting he use the "Jack of Diamonds" killer, perpetrator of a recent double murder, as one of the seven "psychopaths" in his script. Marty writes a story for another psychopath, the "Quaker", who stalks his daughter's killer for decades, driving the killer to suicide and ultimately cutting his own throat to follow him to hell.
Margaret grows up to become a respectable lady in the South, just like her mother May Belle. She wants to become a writer, but her feminist mother insists on her becoming a female doctor. May Belle puts a lot of pressure on her daughter, forcing her to be the best in everything. This results in Margaret never being able to satisfy her mother. When she has become a young lady, all the boys want to be with her, but Margaret only has eyes for Clifford.
TV newswoman Lee Carter (Paula Prentiss) is one of many witnesses to the public assassination of presidential candidate Senator Charles Carroll (Bill Joyce) atop the Seattle Space Needle. A waiter armed with a revolver is chased but falls to his death. Meanwhile, a second waiter, also armed, leaves the crime scene unnoticed. A Congressional special committee determines that the assassination was the work of a lone gunman.
The film features a series of exclusive interviews including discussions with Blair and former executive editor Howell Raines, who stepped down after Blair's plagiarism was uncovered and staff at The Times complained that the breach should have been handled sooner. Raines took the mantle of executive editor in September, 2001, just days before the 9/11 terrorist attacks on The World Trade Center and The Pentagon, leading the paper to "an unprecedented seven Pulitzer prizes." Despite the paper's success under Raines, many reporters expressed feelings of being under pressure and bullied by his demanding management style. Discontent reached an apex after Blair's resignation when a 14,000-word expose of the journalist's plagiarism was published in the Sunday edition of The Times and staff discovered that the paper's metro editor, Jonathan Landman, sent Raines an unheeded memo urging him "to stop Jayson from writing for The Times. Right now.
Miles Raymond is an aspiring – but unsuccessful – writer, a wine aficionado and a divorced, depressed, borderline alcoholic middle-aged English teacher living in San Diego, who takes his soon-to-be-married actor friend and college roommate Jack Cole, on a road trip through Santa Ynez Valley wine country. Though still recognized on occasion, Jack's acting career appears to have peaked years ago, when he co-starred in a popular TV soap but now does commercial voice-overs and plans to enter his future father-in-law's successful real estate business after he's married. Miles wants to spend the week relaxing, golfing, enjoying good food and wine; however, much to Miles' consternation, Jack is on the prowl and wants one last sexual fling before settling into domestic life.
Joan Wilder (Kathleen Turner) is a lonely romance novelist in New York City, whom her editor believes is waiting for a romantic hero like in one of her books. One day Joan gets a call from her sister, Elaine, who has been kidnapped by antiquities smugglers Ira (Zack Norman) and Ralph (Danny DeVito). Joan is to go to Colombia with a map she's just received in the mail from Elaine's late husband; the map is Elaine's ransom.
Sixteen-year-old Jamal Wallace (Rob Brown) plays basketball with his friends in New York. A recluse, William Forrester (Sean Connery), lives on the top floor of the building across from the court. The kids regularly notice him watching them. One of the boys dares Jamal to sneak into the apartment and retrieve an item. Jamal takes a letter opener only to be surprised by Forrester and inadvertently leaves his backpack behind. Forrester later drops Jamal's backpack onto the street. Jamal goes home to find that Forrester wrote notes in his journals. Jamal returns to Forrester's apartment and asks him to read more of his writing. Forrester tells him to begin with 5,000 words on why Jamal should "stay the fuck out of my home", which he completes and leaves on the doorstep the following day.
Lee Jeok-yo (Park Hae-il) is a highly respected national poet in his 70s. His thirtysomething assistant Seo Ji-woo (Kim Mu-yeol) has recently published his first book, described as a genre novel with psychological insight, and it has shot to the top of the bestseller lists. Only later will it be clear how great his debt is to the poet laureate. On finding a young high school girl, Eun-gyo (Kim Go-eun), asleep on a chair on his porch, Jeok-yo is instantly enamored and rather than chastising her for breaking into his property, he subsequently agrees to give her a part-time job cleaning his home. As Jeok-yo spends more time in Eun-gyo's company, long-lost feelings are awakened within him, and her exuberance, lust for life, sense of fun and genuine warmth towards him quickly strip the years away in his mind: he increasingly sees himself as the young man he used to be—his love and need for her growing not only because he finds her incredibly beautiful but also as a direct result of how she makes him feel. Deeply smitten, Jeok-yo begins to write a short story about his imagined sexual relationship with the effervescent young woman. However, as the two get ever closer, Ji-woo finds it impossible to hold back from vocalizing his opposition to what he deems to be an inappropriate and wholly repugnant relationship and, on finding Jeok-yo's manuscript, his abhorrence (and jealousy of both Jeok-yo and Eun-gyo's relationship and the beauty of Jeok-yo's writing) boils over and he decides to steal the short story to publish under his own name.
In 1965, Ibrahim Kadir (played by himself) is falsely arrested after being accused of being a communist or communist sympathizer. While imprisoned, he meets other inmates who have also been falsely imprisoned. Together, they sing the traditional poetic form didong, and attempt to band together. However, every day more prisoners are taken outside and executed.
Miami liquor wholesaler Michael Gallagher (Newman), who is the son of a deceased criminal, awakes one day to find himself a front-page story in the local newspaper, indicating that he is being investigated in the disappearance and presumed murder of a local longshoreman union official, Joey Diaz.
The self-loathing Charlie Kaufman is hired to write the screenplay for The Orchid Thief. Kaufman is going through depression and is not happy that his twin brother Donald has moved into his house and is mooching from him. Donald decides to become a screenwriter like Charlie and attends one of Robert McKee's famous seminars.
Disheartened when his story about Canadian snipers possibly mutilating corpses in Afghanistan is buried, Luke (Nick Stahl) quits his job but is even more determined to return to Afghanistan to get the real story. With his offbeat buddy, Tom (Nicolas Wright), tagging along, Luke returns to Afghanistan and intends to gather enough evidence to get his old story into print. But he soon finds that the country is an even more dangerous place than when he left. To make matters worse, his old friend and fixer, Mateen (Stephen Lobo) has been hired away by Luke's journalistic nemesis, Imran Sahar (Vik Sahay). Soon the trip for Luke and Tom in Afghanistan turns into a surreal and perilous adventure, a journey into an alternate reality, filtered through a haze of gun smoke. They encounter Taliban raids, bombings and unfinished business with an Afghanistan businessman. Luke still makes his way through the wilderness with Canadian troops and Arabian guides to find out if his story is true or not. In the end, he realises that the rumour about Canadians mutilating fingers is a lie and that his people still have some morality in this war torn land. Just as he is about to leave, He and Sgt. Rick (a Canadian soldier who is the leader of the squad with whom he had been travelling) come under fire from a Taliban sniper, but the Taliban runs out of bullets and walks off, while Luke thinks he killed him. While they move back to the base, Luke runs into Matteen, where he finds out that they really do share a friendship. The last scene is where Luke decides to go home.