- A prep school student needing money agrees to "babysit" a blind man, but the job is not at all what he anticipated.
- Frank is a retired Lt. Col. in the US Army. He's blind and impossible to get along with. Charlie is at school and is looking forward to going to university; to help pay for a trip home for Christmas, he agrees to look after Frank over Thanksgiving. Frank's niece says this will be easy money, but she didn't reckon on Frank spending his Thanksgiving in New York.—Rob Hartill
- Charlie Simms is a boy from Oregon who attends Baird School a Boys boarding school. Unlike most of the other boys who come from affluent backgrounds Simms comes from the working class and is there on a scholarship. He hangs around with George Willis, who's a daddy's boy, and his friends. Now George's friends decides to pull a little prank on the pompous headmaster. The headmaster learns that Charlie and George know who pulled the prank and they refuse to say who. He gives them the Thanksgiving Holiday to think about it. He also tells Charlie that he's recommending him to an Ivy League College. Charlie then goes off to a Thanksgiving job--taking care of retired Colonel Frank Slade who's blind when his family goes to visit some family for Thanksgiving. After they leave Slade tells Charlie that he's taking him to New York for his own Thanksgiving celebration.—rcs0411@yahoo.com
- In New Hampshire, Charlie Simms attends the Baird School, an all boys boarding school with rigorous classes and expensive enrollment. Yearning for cash from a part-time job so he can return to his family in Oregon for upcoming Christmas Break, the innocent Simms accepts a job for "babysitting" at a nearby household. The job is not what he expects, for he is commissioned to watch over an unlikeable, blunt behaved blind ex-colonel named Slade who has a keen ability at selecting his aides. Because of his sympathetic and integral nature, Charlie agrees to the job. Before he can even locate his level of comfort in the job, Simms is unexpectedly taken to New York City with the colonel, where the ex-military man has several agendas of his own.—commanderblue
- Charlie Simms (Chris O'Donnell) is a student at an exclusive New England prep school called Baird. Unlike most of his peers, Charlie was not born to a wealthy family. Charlie comes from Oregon and his stepfather and mother run a grocery store together. Charlie won a Young America merit scholarship to attend Baird.
To pay for a flight home for Christmas, Charlie accepts a temporary job over Thanksgiving weekend looking after a retired Army Ranger Lieutenant Colonel Frank Slade (Al Pacino). Charlie meets Frank, a highly decorated, blind Vietnam War veteran who has become an alcoholic. Frank served the armed forces for 26 years. Frank lives with his niece Karen Rossi (Sally Murphy) and her husband Donny (Michael Santoro), who are going away for a Thanksgiving weekend and hence need a caretaker for Frank. Frank was at an old age home, but didn't like it there, so Karen took her in. Karen is paying Charlie $300 for the weekend, even though Frank is livid at everything Charlie says.
Charlie and George Willis, Jr. (Philip Seymour Hoffman), another student at the preparatory school, bear witness to several students setting up a prank for the school's headmaster Trask (James Rebhorn). The students (Harry (Nicholas Sadler), Trent (Todd Louiso) and Jimmy) were mocking a new Jaguar given to Trask by the school board. They install a paint bag over Trask's parking spot at night, and when Trask parks his car there in the morning, they blow up the paint bag to ruin the Jaguar as well as Trask's suit. Mrs Hunsaker (June Squibb) had seen Willis and Charlie at night, who distracted her so she could not properly look at the pranksters.
Following the prank, Trask presses Charlie and George to divulge the names of the perpetrators. When Charlie refuses to talk, he privately threatens Charlie with withdrawing the recommendation that he has already drafted (but not yet sent) that Charlie be accepted by Harvard University. Trask schedules a meeting of the school disciplinary committee to take place on the Monday after the Thanksgiving weekend. Charlie continues to remain silent but appears conflicted. Willis tells Charlie to stick with the group and not to squeal on fellow students.
Shortly after Charlie arrives, Slade unexpectedly whisks Charlie off on a trip to New York City. Slade reserves a room at the Waldorf-Astoria. During dinner in the Oak Room at the Plaza Hotel, Frank reveals that the goals of his trip are to stay at a luxurious hotel, enjoy good food and wine, visit his older brother, and have sex with a "terrific" woman. Afterward, he intends to die by suicide. Charlie is taken aback and does not know if Slade is serious.
They pay an uninvited surprise visit to Slade's brother's home for Thanksgiving dinner. Slade is an unpleasant surprise for the family, as he deliberately provokes everyone and the night ends in acrimony. Slade ends up in a confrontation with his nephew Randy (Bradley Whitford), who reveals that Frank was not blinded heroically in combat, but rather by grandstanding by juggling live grenades for a group of younger officers.
As they return to New York, Charlie tells Slade about his complications at school. Slade advises Charlie to inform on his classmates and go to Harvard, warning him that Willis will probably be pressured into not maintaining silence. Later at a restaurant, Charlie and Slade observe Donna (Gabrielle Anwar), a beautiful young woman waiting for her date. Although blind, Slade leads Donna in a spectacular tango ("Por Una Cabeza") on the dance floor. That night, Slade hires an escort.
Deeply despondent the next morning, Slade responds to Charlie's suggestion that they test drive a Ferrari. A former Ferrari owner, Frank talks the salesman into letting them take a convertible for a test ride. Charlie lets Slade drive the car and Slade begins speeding, attracting the attention of a police officer (Ron Eldard), who Slade manages to appease without giving away his blindness.
After returning the car, Frank again becomes despondent. He jaywalks into rushing traffic on Park Avenue and narrowly avoids being struck by multiple cars. When they return to the hotel, Frank sends Charlie to buy cigars. Charlie initially leaves the room but quickly becomes suspicious. Charlie leaves but becomes suspicious and returns to find Frank donning his dress uniform, preparing to end his life with his service pistol. Frank backs down after Charlie convinces him that he has much to live for and should courageously face his circumstances.
The two return to New England. At school, Charlie and Willis are subjected to a formal inquiry in front of the student body and the student/faculty disciplinary committee. As headmaster Trask is opening the proceedings, Slade unexpectedly returns to the school, joining Charlie on the auditorium stage for support. For his defense, Willis has enlisted the help of his wealthy father, and divulges the names of the perpetrators, qualifying that his vision wasn't clear. When pressed for more details, Willis passes the burden to Charlie.
Although struggling with his decision, Charlie gives no information, so Trask recommends Charlie's expulsion. At this, Slade cannot contain himself and launches into a passionate speech defending Charlie and questioning the integrity of a system that rewards informing on classmates. He tells them that Charlie has shown integrity in his actions and for the committee to not expel him because this is what great leaders are made of and he will make them proud in the future. The disciplinary committee decides to place on probation the students named by Willis, and to give Willis neither recognition nor commendation for his testimony. They excuse Charlie from any punishment to loud applause from the student body.
As Charlie escorts Slade to his limo, a female political science teacher Christine Downes (Frances Conroy), who was part of the disciplinary committee approaches Slade, commending him for his speech. Seeing a spark between them, Charlie tells the teacher that Slade served on President Lyndon Johnson's staff. A romantic prospect is hinted between Slade and the teacher as they part ways. Charlie takes Slade home, where they part ways. The colonel walks towards his house and greets his niece's young children happily.
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