The opening sequence takes the form of a computer simulation run by the Devil to analyze souls and determine individual weaknesses to exploit and corrupt. The program finally settles on Elliot Richards (Brendan Fraser), a geeky, over-zealous man working a dead-end technical support job in a San Francisco computer company. He has no friends and his co-workers are always avoiding him. He has a crush on his colleague, Alison Gardner (Frances O'Connor), but lacks the courage to ask her out. After Elliot is again ditched by his co-workers at a bar while trying to talk to Alison, he says to himself that he would give anything for Alison to be with him. The Devil, in the form of a beautiful woman (Elizabeth Hurley), overhears him and offers to give Elliot seven wishes in return for his soul.
As a test, he wishes for a Big Mac and Coke. The Devil takes him to McDonald's and places the order. Elliot has to pay for it, because, "there ain't no such thing as a free lunch." After taking Elliot to her office, based at a nightclub in Oakland, the Devil convinces Elliot to sign her contract, and delivers further wishes. Each wish has Elliot living them out with Alison and his co-workers in surrogate roles. However, he doesn't know that the Devil will always spoil his wishes by adding something he doesn't want. Elliot wishes to be rich and powerful, with Alison as his wife. The Devil makes him a Colombian drug lord whose wife despises him and cheats on him with Raoul, his co-worker, who is secretly planning to get rid of Elliot and take his position and property. Soon after there is a firefight between his and Raoul's people where Elliot "dies". When he returns to the real world, the Devil points out that he never wished for Alison to love him.
Secondly, Elliot wishes to be emotionally sensitive so he will understand the needs and desires of women. The Devil makes him so sensitive that he spends most of his time crying over how beautiful the world is, and constantly asks Alison, his girlfriend of "three magical weeks," whether he has hurt her or if she needs anything. Alison says she has had enough of it and wants to be with a man who is strong and shallow. She then leaves Elliot for a man who is strong, rude and completely different from the romantic and emotionally sensitive Elliot. Elliot then wishes to be a superstar athlete who would be a woman magnet. The Devil makes him a cliché-spewing NBA star, but also gives him a small penis and a low IQ, which causes Alison, a sports reporter, to lose interest in him shortly after they meet.
He then wishes to be intelligent, witty and well-endowed. The Devil grants this by making him a famous writer whom Alison falls in love with at a cocktail party. When they arrive at Elliot's home to make love it is revealed that Elliot is gay and living with a flamboyant male partner. Lastly, Elliot wishes to be President of the United States to try to improve the world and get Alison to take him seriously. The Devil makes him Abraham Lincoln at Ford's Theatre on the night of his assassination which he barely avoids. After each wish is renounced, Elliot meets with the Devil and she blames him for not being specific enough. Eventually he returns to work, thinking about what he should do with the last two wishes. The Devil then appears on the computer screen, pointing out that he only has one wish left. This is because on their first meeting he asked for a Big Mac and Coke, although she had stated that it was a test wish and granted it before Elliot signed the contract. Elliot loses his patience and storms out of his office.
Elliot visits a church looking for God's help, where he briefly confesses to a priest who seems sympathetic. However, after being asked whether he thinks asking the Devil for a Big Mac and Coke counts as a wish, the priest, believing he is drunk, has Elliot arrested. The sergeant books him, and the Devil, dressed as a police officer, throws him in a cell, telling him that she does like him, and it would not hurt to have her as a friend. Elliot's cellmate (Gabriel Casseus) tells him that he cannot possibly sell his soul as it belongs to God, and although the Devil may try to confuse him, in the end he will realise who he truly is, and what his purpose is. Elliot questions the man as to his identity, but the response is simply "a really good friend".
Elliot asks the Devil to cancel their contract. When the Devil refuses, Elliot states he will not use his final wish. The Devil teleports them to Hell, where she transforms first into a black horned monster, then into a giant. When the Devil pushes him to make a final wish, Elliot wishes that Alison could have a happy life - with or without him. The Devil sighs and Elliot falls into the depths of Hell. He wakes up on a marble staircase, wondering if it is Heaven. The Devil tells him that because a provision in the contract's fine print, unread by Elliot, states that a selfless wish voids the contract, Elliot keeps his soul. Elliot admits that despite her manipulation of him he has come to like the Devil and regards her as a friend, something she does not object to. She also advises that Heaven and Hell can be found on Earth; it is up to humans to choose. Elliot finally asks Alison out, only to learn that she is already dating another man. He continues with his life, but with a better understanding of who he is.
Later Elliot is confronted by Bob, one of his co-workers, who starts ridiculing Elliot at the encouragement of his co-workers. Elliot loses his temper and grabs a terrified Bob by the shirt, but lets go, simply saying, "Nice talking to you." A threatening look sends his other co-workers scurrying away in fear. At home, he meets a new neighbor, Nicole Delarusso (also played by Frances O'Connor), whose looks resemble Alison's but whose personality, interests and fashion sense are much closer to his. He offers to help her unpack and they begin a relationship. While the two walk along a boulevard, the Devil and Elliot's cellmate, both dressed in white, are seen playing chess, looking at Elliot and his new girlfriend, with the Devil taking the opportunity to fix the game but getting caught by the guy, who only laughs about that and let her finish her cheating moves. The scene ends with the Devil's computer program listing foibles of Nicole's and Elliot's, which they both tolerate.Brendan Fraser as Elliot Richards / Jefe / "Mary" / Abraham Lincoln
Elizabeth Hurley as The Devil
Frances O'Connor as Alison Gardner / Nicole Delarusso
Orlando Jones as Daniel / Dan / Danny / Esteban / Beach Jock / Lamar Garrett / Dr. Ngegitigegitibaba
Paul Adelstein as Bob / Roberto / Beach Jock / Bob Bob
Toby Huss as Jerry / Alejandro / Beach Jock / Jerry Turner / Lance
Miriam Shor as Carol / Penthouse Hostess
Gabriel Casseus as God
Brian Doyle-Murray as Priest
Jeff Doucette as Desk Sergeant
Aaron Lustig as Synedyne Supervisor
Rudolf Martin as Raoul
Julian Firth as John Wilkes Booth
The film received mixed reviews from critics. Film aggregator Rotten Tomatoes gave it 49% based on 113 reviews, with an average of 5.5/10. The general consensus states: "Though it has its funny moments, this remake is essentially a one joke movie with too many flat plots." The movie was a box office success.