Six months after the events in Romancing the Stone, Joan Wilder (Kathleen Turner) is having trouble writing her next romantic novel while living with Jack Colton (Michael Douglas) on his boat, the Angelina, which is moored in a South of France port, and she refuses to discuss marriage. Later that afternoon at a book signing engagement held by her publisher, Gloria (Holland Taylor), Joan meets a charming Arab ruler named Omar (Spiros Focás) who has managed to persuade the world that he is the firm, but fair, ruler of Kadir. Omar offers Joan the opportunity to live like a queen at his palace, while she writes a puff piece about him. However, as soon as Joan leaves with Omar, Jack runs into Ralph (Danny DeVito). Ralph, a comical swindler from Jack's past, recently out of prison, plans on killing Jack for abandoning him to the authorities in Colombia, but is stopped by an Arab named Tarak (Paul David Magid), who tells Jack of Omar's true intentions. This includes the fact that he has their greatest treasure, the Jewel of the Nile, in his possession. Ralph, immediately interested at the prospect, agrees to help find the Jewel. Jack, however, is less than convinced. But seconds later, the Angelina explodes, having been sabotaged under Omar's orders. He then agrees to team up with Ralph and Tarak in order to track down the lost jewel in Omar's kingdom.
Successful author Mort Rainey (Johnny Depp) suffers a psychotic break when his wife has an affair with a man named Ted (Timothy Hutton). He puts off finalizing the divorce by retreating to his secluded cabin in the rural town of Tashmore Lake in upstate New York. Depressed and suffering from writer's block, Mort is confronted one day by the mysterious John Shooter (John Turturro), a Mississippi dairy farmer who accuses him of plagiarism. Shooter leaves Mort with his manuscript "Sowing Season" which he alleges was copied. Mort dismisses Shooter as a lunatic and throws the manuscript away, but his cleaning lady digs it out of the trash and presents it back to him. With his curiosity piqued, Mort reads the story and is surprised to discover its resemblance to his own story "Secret Window".
In 1997, Sarah Huttinger (Jennifer Aniston), an obituary and wedding announcement writer for The New York Times, travels to Pasadena, California, for her sister Annie's (Mena Suvari) wedding, accompanied by her fiancé Jeff Daly (Mark Ruffalo). At a pre-wedding party, Sarah learns from her grandmother Katharine (Shirley MacLaine) that her mother Jocelyn ran off to Cabo San Lucas to spend time with her prep school classmate Beau Burroughs (Kevin Costner) the week before her wedding to Sarah's father Earl (Richard Jenkins). Jeff points out Sarah's parents were married just short of nine months before her birth, leading her to wonder if Beau might really be her biological father. Sarah also discovers her grandmother might have been the inspiration for Mrs. Robinson, an infamous character in the novel The Graduate.
One night, a thief fleeing through Georgetown in Washington, D.C., is shot by a man carrying a briefcase. A pizza delivery man who witnesses the incident is also shot by the killer and is left in a coma. The following morning, a young woman is killed by a Washington Metro train in what seems to be suicide. Congressman Stephen Collins (Ben Affleck) is distraught to hear that the woman was Sonia Baker (Maria Thayer), a lead researcher on his staff. Collins, who has military experience, is leading an investigation into PointCorp, a private defense contractor with controversial operations involving mercenaries. Collins tells his former college roommate and old friend Cal McAffrey (Russell Crowe), an investigative reporter, that he had been having an affair with Sonia and that she had sent him a cheerful video message on the morning of her death, which he says is inconsistent and unusual behavior for someone about to commit suicide.
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.
On July 4, 1969, an unknown male attacks Darlene Ferrin and Mike Mageau with a handgun, at a lovers' lane in Vallejo, California. Mageau survives; Ferrin dies.
The film opens with Super 8 footage depicting a family of four standing beneath a tree with sacks over their heads and nooses around their necks. An unseen figure saws through a branch acting as a counterweight, causing their deaths by hanging.
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.
In 1887, Edith Cushing, the young daughter of wealthy American businessman Carter Cushing, is visited by her mother's ghost who warns her, "beware of Crimson Peak."
Reporter Rowena Price, under the pseudonym of David Shane (Halle Berry), and researcher Miles Haley (Giovanni Ribisi) are investigating conservative Republican senator Stephen Sachs, who has been having secret sexual encounters with his male interns, despite his publicly anti-gay agenda. The story is shut down, however, when the source clams up and Rowena's editor, a supporter of the senator, puts a stop to the story. The editor also insists she take a vacation and won't take no for an answer.
In June 1972, a security guard (Frank Wills, playing himself) at the Watergate complex finds a door kept unlocked with tape. He calls the police, who find and arrest five burglars in the Democratic National Committee headquarters within the complex. The next morning, The Washington Post assigns new reporter Bob Woodward (Robert Redford) to the local courthouse to cover the story, which is thought to be of minor importance.
In 1984 East Germany, Stasi Captain (Hauptmann) HGW XX/7, Gerd Wiesler, suggests to his superiors that he begin to spy on the playwright Georg Dreyman. Wiesler and his team bug the apartment, set up surveillance equipment in an attic and begin reporting Dreyman's activities. Dreyman had escaped state scrutiny due to his pro-Communist views and international recognition. Wiesler soon learns the real reason behind the surveillance: Minister of Culture Bruno Hempf covets Dreyman's girlfriend, actress Christa-Maria Sieland, and is trying to eliminate Dreyman as a romantic rival. While Wiesler's superior, Lt. Col. Anton Grubitz, sees an opportunity for advancement, Wiesler, an idealist, is horrified, asking Grubitz "Is this why we joined?" Minister Hempf coerces Sieland into having sex with him by exploiting her vulnerability as an insecure actress whose livelihood is dependent on state approval of stagecraft. After discovering Sieland's relationship with Hempf (through Wiesler's covert intervention), Dreyman implores her not to meet him again. Sieland flees to a nearby bar where Wiesler, posing as a fan, urges her to be true to herself. She returns home and reconciles with Dreyman, rejecting Hempf.
In a short prelude, U.S. Army General Hopgood (Stephen Lang) is painfully thwarted in an attempt to pass paranormally through a solid wall by simply running into it. The film then follows Ann Arbor Daily Telegram reporter Bob Wilton (Ewan McGregor), whose wife leaves him for the newspaper's editor. Seeking an escape, Bob flies to Kuwait to report on the Iraq War and to prove to his wife and himself that he is a man. However, he stumbles onto the story of a lifetime when he meets a retired U.S. Army Special Forces operator, Lyn Cassady (George Clooney), who reveals that he was part of a U.S. Army unit training psychic spies (or "Jedi Warriors") to develop a range of parapsychological skills including invisibility, remote viewing, and phasing. The back story is told mainly through flashbacks.
The film centers on Manuela, an Argentine nurse who oversees donor organ transplants in Ramón y Cajal Hospital in Madrid and single mother to Esteban, a teenager who wants to be a writer.
The film revolves around three characters who work in television news. Jane Craig (Hunter) is a talented, neurotic producer whose life revolves around her work. Jane's best friend and frequent collaborator, Aaron Altman (Brooks), is a gifted writer and reporter ambitious for on-camera exposure who is secretly in love with Jane. Tom Grunick (Hurt), a local news anchorman who until recently was a sports anchorman, is likeable and telegenic, but lacks news experience and knows that he was only hired for his good looks and charm. He is attracted to Jane, although he is also intimidated by her skills and intensity.