A comedic look at the relationship between a wealthy man with quadriplegia and an unemployed man with a criminal record who's hired to help him.
The film opens with Dell Scott driving Philip Lacasse through the city of Chicago. They are followed by police after Dell starts to speed up. He bets Philip that he can lose the cops, and he does for a moment until they corner him in the streets. They force Dell out of the car until he tells them that he was rushing to the hospital because Philip is having a seizure. They see him foaming at the mouth and then escort the two to the hospital, but they are just faking it and laugh over the cops believing them.
Six months earlier.
Dell is recently released convict who is meeting with his parole officer to try and turn his life around. He must obtain a number of signatures and hand them in by the next day. He goes around to different workplaces with little to no interest in what they offer other than the signatures. Dell's last stop is Philip's home. As he is a quadriplegic, Philip interviews several candidates alongside his assistant Yvonne Pendleton for the position of Philip's caregiver. Dell waits for over an hour to be called in, and he barges in during an interview demanding to be met because he has to go meet his son. Philip decides to listen to Dell's story, and when he mentions doing time in prison, Philip asks what he was in for. Dell tries to change the subject by turning it around on him and says that he must be offered the job after being asked that question. Philip does so, but Dell declines, as he is not interested in being hired and only wants the signature.
Dell goes to a school to pick up his son Anthony, but he is told by someone that his mother picked him up. Dell visits Anthony and his ex-wife Latrice. Neither of them has much interest in Dell trying to be there now, what with him being absent for most of Anthony's life. It doesn't help that he and Latrice live in a crummy apartment that is falling apart. Dell gives Anthony a storybook for his birthday, except it's a book he swiped from Philip before leaving.
Dell is contacted by Yvonne to come back as Philip wants to hire Dell for the job, simply because he was the worst and least qualified candidate. She doesn't trust Dell due to his criminal history and is concerned for how Dell will handle Philip, but he assures her he can do a good job. Yvonne establishes a three strikes rule on Dell to make sure he doesn't screw up, and she lets him know that the job is a live-in position, and it pays very well since Philip is so wealthy.
Dell starts off rocky as he isn't quick to respond to Philip's calls via opera music, or he just makes things like feeding Philip his breakfast a daunting task. Dell meets Philip's nurse Maggie, who shows Dell how to take care of Philip physically. This involves demonstrating the use of a catheter and how it is applied, to Dell's discomfort. Slowly, Dell starts to adjust to Philip's needs and acts better. However, Philip insists to Dell that he follow a strict DNR (do not resuscitate) rule if Philip stops breathing. This is put to the test one night as Philip appears to be suffocating, but Dell, insisting he needs the job, gives Philip oxygen and forces him to breathe.
After getting his first paycheck, Dell goes to find Latrice and give the whole thing to her and Anthony. She is somewhat pleased until Dell asks her to get the book back from Anthony since it wasn't his to give. Latrice gets upset once again and tells Dell to do his own dirty work. He then goes to find Anthony but finds him talking to a suspicious older man. Dell misses Anthony before he enters his building and has to leave when he sees some kids messing around with Philip's car that Dell was allowed to drive. He is then contacted by Yvonne, and when he returns to Philip's home, Yvonne calls his absence his third strike and tries to fire him until Philip clarifies that he allowed Dell to take the car to see his son.
Dell takes Philip around the city after smoking a joint to ease a pain that Philip feels in his legs. During their walk, Philip tells Dell how he became a quadriplegic. His late wife Jenny was suffering from cancer at the time, and so Philip proposed that they go paragliding to take her mind off of things. It was this accident that rendered Philip immobile. He cries as he thinks about Jenny. Dell tries to cheer him up by taking him to get food. During their talk, Dell also discusses potential business ideas he would like to get into with Philip's help.
Dell finds out that Philip is in an epistolary relationship with a woman named Lily Foley. They maintain a correspondence without having seen pictures of each other or hearing each other's voices. Dell goes through Lily's letters and finds a phone number. Against Philip and Yvonne's words, Dell calls Lily, but they only get her voicemail. Dell encourages Philip to say something, and so he asks her to call him back whenever she can.
Philip joins Dell as he takes Anthony out for the day. Everything goes well and they have fun until Dell asks Anthony for the book back, and Anthony realizes it belongs to Philip. He gives it back to Philip but walks away from Dell.
Dell and Philip go home to find that Yvonne has organized a surprise party for Philip's birthday. He is displeased, as he doesn't want anything like that. He orders Yvonne to get rid of the guests while he and Dell have an argument, which leads to Dell smashing things for Philip's catharsis. They decide to let the party continue and mingle. Dell even gets Yvonne to dance. Meanwhile, a neighbor named Carter that Philip can't stand approaches him about Dell's criminal record and to reconsider keeping Dell around for the sake of the other residents in the building, but Philip ignores Carter. Yvonne then goes to Philip to tell him that Lily has called back and would like to set up a dinner date.
Dell sits with Philip in a restaurant a few days later as they wait for Lily to show up. Philip gives Dell a check for $50,000 for a silly painting Dell did, but Philip wants Dell to put it to good use and invest it in a potential business. Lily then arrives, and she insists that Dell doesn't need to be there to help Philip. However, during the meal, Lily admits that while she knew about Philip's condition, the whole thing wasn't what she was expecting. Philip becomes quietly offended and tries to leave, but he accidentally bumps into another patron, and then a waiter who spills hot coffee on his lap. The staff clamor around Philip to help him as he insists he can't feel a thing.
Dell goes to pick Philip up and return him home, but Philip chews Dell out for arranging the whole thing with Lily since he now feels like a fool. Philip then fires Dell.
Time passes by, and Dell decides to spend Philip's check toward buying a better apartment for Latrice and Anthony. He gets a new job working with auto parts, but he is approached by Maggie, who says that Philip has gone through several other caregivers and hasn't communicated with any of them, and he just won't talk to anybody else, which has led Yvonne to leave. Maggie tells Dell that she thinks Philip will listen to him.
Dell goes to find Philip, who hasn't had a shave in a while. He takes him out for a drive, which leads to the encounter with the police and faking a seizure. They flee before the nurses arrive with a gurney.
Dell continues to drive out of town until they reach a spot where Philip can relax. Dell arranges for Philip to go paragliding again to get over his fear of it, but Dell unwittingly has to join him. After the event, Dell brings Philip to a house where he surprises him by having Yvonne show up. Dell leaves the two of them to catch up while he goes to spend the day with Anthony.