This film is written by Robert Dunn, Paul Guay and Stephen Mazur. It was the third collaboration by Guay and Mazur, whose previous comedies were The Little Rascals and Liar Liar.
Max and Page Conners (Sigourney Weaver and Jennifer Love Hewitt) are a mother-daughter con artist team. When the film opens, the Conners are finishing a con on Dean Cumanno (Ray Liotta), an auto-body shop owner and small-time crook. The con, which the Conners have played many times before on other men, involves Max marrying Dean, passing out on their wedding night to avoid consummating the marriage, and then Page (posing as Dean's secretary) luring Dean into a compromising position to justify Max's immediate divorce and hefty settlement. The con is a success.
Page declares that she wants to go solo. Max initially relents, but when they go to the bank to split their earnings, they're confronted by an IRS agent (Anne Bancroft) who declares that they owe the government a considerable sum on top of the rest of their savings, which have already been seized. Page reluctantly agrees to work one last con with Max in Palm Beach, to get enough money to pay off the IRS and set Page up to work on her own. For their target, they choose widower William B. Tensy (Gene Hackman), a tobacco baron who is addicted to his own product.
While working the main con with Tensy, Page attempts a side con without her mother's knowledge. Page targets beachfront bartender Jack (Jason Lee), who is worth $3 million, but develops genuine feelings for him. Max learns of the side con and tells Page to break the relationship off, which Page does reluctantly.
Tensy proposes to Max ahead of schedule, but before they can get married, he accidentally chokes and dies while trying to initiate sex with Max. While Max and Page are deciding what to do with the body, Dean arrives, having tracked Max down to apologize and propose to her again. Dean figures out that Max and Page conned him, and threatens to call the authorities. Max offers to return Dean's divorce settlement money if he'll help them make Tensy's death look like an accident. Max tells Page that their money wasn't really taken by the IRS; the agent was Max's mentor, Barbara, who agreed to help prevent Page from leaving. However, when Max, Page and Dean go to the bank, the money really has gone, having been liquidated in an act of betrayal by Barbara.
In order to help Max, Page returns to Jack and accepts his proposal, planning to work it as a regular con. Page insists that Jack will not cheat on her, but is heartbroken when, on their wedding night, she breaks into her mother's room and finds him in a compromising position with Max. After the divorce settlement is paid, Dean confronts Max about the ethics of their con, pointing out that even a "goody-goody" like Jack is only human. Max reveals that Jack actually turned her down and that she had to drug him, but she defends her actions by saying that Jack would hurt Page eventually. Dean counters that Max has no right to keep Page from the man she loves because of what "might" happen.
Chastened, Max tells Page the truth, admitting that her efforts to protect her daughter have only hurt her in other ways. Page returns to Jack, giving him back the bar he'd had to sell to pay the settlement, and tells him her real name. Max and Dean also get together, Dean having admitted that he still loves Max despite what she put him through. The final shot of the film is of Dean — using the name 'Stanley' — romancing Barbara, with Max watching them via binoculars, implying that Max and Dean are now working together to get Max's money back from Barbara.Sigourney Weaver as Max Conners, con-artist
Jennifer Love Hewitt as Page Conners, Max's daughter, fellow con-artist
Ray Liotta as Dean Cumanno, Max's love interest
Jason Lee as Jack Withrowe, Page's love interest
Anne Bancroft as Gloria Vogal/Barbara, Max's longtime friend and mentor in "the con" game
Jeffrey Jones as Mr. Appel, hotel manager in Palm Beach
Gene Hackman as William B. Tensy
Nora Dunn as Miss Madress, Tensy's housekeeper
Julio Oscar Mechoso as Leo, Dean's friend & security guard
Ricky Jay as Dawson's Auctioneer
Sarah Silverman as Linda, Jack's friend and waitress
Zach Galifianakis as Bill, Jack's friend and fry cook
Michael Hitchcock as Dr. Arnold Davis
Carrie Fisher as Ms. Surpin, Max's divorce attorney
Elya Baskin as Vladimir, Kremlin Waiter
The film had been in the works for quite a long time. Originally, Ang Lee was set to direct with Anjelica Huston and Alicia Silverstone playing the roles of "Max" and "Page". However, due to the long pre-production stage, both actresses had to bow out of the film due to scheduling conflicts. In 1999, it was then announced that Huston and Cameron Diaz were set to play the two leading roles, with Doug Liman directing but then Liman backed out of the project, creating quite a long time frame to find a new director. Huston and Diaz both had to bow out as well. Cher became attached and brought in David Mirkin to direct and rewrite the script. Jennifer Aniston also became attached at this time. Cher then dropped out to do a world tour for her unexpected #1 hit album Believe and the mother/daughter roles went to Sigourney Weaver and Jennifer Love Hewitt. R&B singers Whitney Houston and Brandy Norwood were briefly considered for the leading mother/daughter roles. Norwood's touring schedules did not allow her to commit to the film and Houston's drug battle prevented her from working at the time.
Filming took place from April 24, 2000 and ended on August 1, 2000
The film was set in Palm Beach, Florida (specifically the Breakers Hotel); according to the DVD commentary by director David Mirkin, only a few external shots were actually shot in Palm Beach, with the rest utilizing Los Angeles locations as stand-ins. The film contains several references to The Beatles, including Sigourney Weaver singing a Russian folk version of "Back in the U.S.S.R." and the use of John Lennon's "Oh My Love" in several key scenes.
Danny Elfman composed the main theme, John Debney composed the score for the film, and among others Inara George contributed the song Infinity.
The film opened at #1 in the U.S. box-office, earning $12.3 million on its opening weekend. It went on to gross a total of $57,756,408 worldwide. Film critic Roger Ebert gave the film three stars out of four and said that, "it does what a comedy must: It makes us laugh."
The film holds a 53% rating on Rotten Tomatoes based on 119 reviews. At Metacritic, it holds a "mixed or average reviews" score of 47 out of 100.
The film was released on VHS and DVD on 2 October 2001. The Film was released on Blu-ray Nov 24, 2015.