Chris is a teenager growing up as the eldest of three children in Brooklyn, New York during the early 1980s. Uprooted to a new neighborhood and bused to a predominantly white middle school two-hours away by his strict, hard-working parents, Chris struggles to find his place while keeping his siblings in line at home and surmounting the challenges of junior high.
As a first-time high school student, Chris (Tyler James Williams) is really looking forward to attending a school with some diversity. Unfortunately, when he arrives at school, he discovers that the school's new principal, Ms. Morello (guest star Jacqueline Mazarella), has placed him in the only all-white homeroom.
Chris agrees to help a classmate, Angel improve his grades if Angel will help him get the attention of Chris' latest crush, Maria.
Chris is thrilled when Jenise Huckstable asks him to the homecoming dance. His nerves begin to get the better of him when Jenise tells him that her father Dr. Clint Huckstable wants to meet him before the dance. Drew tries to get Doc to feng shui the store when he takes over Chris' hours.
After Julius and Rochelle raise the rent, Mr. Omar demands reparations and moves in with the family while his apartment is being repaired. While there, he begins to play blackjack with Drew and Tonya using real money. Meanwhile, Chris is assigned to do a book report and decides to watch the movie instead of reading the book as an easy way out. However, as he later learns from Greg, the movie he saw did not match the book assigned.
Although warned by Greg that it's a bad idea, Chris starts to help the football team with their homework as a means to socialize with the cool kids. As a result, Chris ends up failing his own exams. Meanwhile, Julius begins a new job collecting dead bodies for Mr. Omar's funeral home and soon finds himself appreciating life more. He begins to buy numerous gifts for his friends and relatives, but then ends up with financial troubles.
Doc has a new girlfriend who is making life hard for Chris so he decides it's time to get her to move on. Rochelle is not happy when she finds a bra in Julius' sock draw, but what she doesn't know is that Tonya is the one that hid it there.
Chris has a dilemma when a reward is offered for anyone who witnessed a shoot-out outside a movie theater. Chris was there but he was supposed to be babysitting Tonya and Drew - what will he do? Meanwhile, Julius and Rochelle have a very eventful anniversary at a Broadway musical.
When the dorkiest girl in school, who everyone calls "Big Bird", asks Chris out on a date, he agrees but only to spare her feelings. He soon realizes after spending time with her that he genuinely likes her.
Julius begins to take marriage advice from "The Oprah Winfrey Show" leading Rochelle to suspect an affair. Meanwhile, Chris volunteers for the "Big Brothers" program and is shocked when he learns the identity of is his "little brother".
New Year's Eve in Times Square is something Chris really wants this year but needs an adult to accompany him. And that is where problems arise... Meanwhile, Tonya and Drew make a bet to see who stays up the longest and Julius becomes a local hero.
When Rochelle orders a copy of her birth certificate, she realizes that she is actually one year younger than she thought she was and decides to start living her life with a new, younger attitude. After a complete stranger helps Chris to safety during a city-wide blackout, Chris decides to repay the older man by getting him out to meet new friends. Meanwhile, Greg feels like he has no identity after realizing that everyone at school knows him only as "Chris and Greg."
Chris and Greg decide to join the wrestling team to earn a varsity jacket in order to impress the ladies. Meanwhile, Rochelle attempts to lose weight by drinking a popular weight-loss drink which gives Julius a money-saving idea and Tonya jeopardizes Drew's all-girl singing group.
In order to attend an age-restricted concert, Chris and Greg try to get themselves a fake ID. Elsewhere, Rochelle plans Julius' surprise party, and Drew tries returning a pair of faulty X-ray vision glasses he bought in the mail.
Rochelle inadvertently prevents Chris from "cramming" for an upcoming PSAT test by taking the family out to a social event. Knowing a good score will help him get into college, Chris resorts to cheating...
Coach Thurman spots Caruso bullying Chris and suggests he take up boxing to defend himself. Meanwhile, Julius has a new set of problems when he suspects Rochelle of adultery and catches the eye of a female neighbor...
Chris reluctantly agrees to hide away some marijuana for a fleeing crook, and now must find someplace to store it before he gets in trouble. Meanwhile, Peaches helps Rochelle learn a new computer system at the beauty salon.
While test driving a car, Chris accidentally hits Greg. Greg ends up in a hospital for a broken leg. Since Greg's parents are out of town, Rochelle drops her vacation plans to take care of him, which leaves Julius to entertain the kids at the shore where it usually rains each day.
After Chris gets his driver's license, Rochelle and Julius give him permission to buy a car, but when the car is stolen and vandalized Chris realizes owning a car is a huge responsibility. While looking for her secret stash of cigarettes, Rochelle comes across Julius' hidden racing form.
Chris decides to take a stand against his mother, Rochelle, and refuses to do his household chores, causing Rochelle to complain to Julius that her son is disrespecting her. Meanwhile, Mr. Omar thinks he's dying and decides to start saying whatever is on his mind.
Chris is shocked when Tasha agrees to be his girlfriend. But he is even more shocked when he discovers how much of his free time would disappear by having a girlfriend. Meanwhile, Rochelle discovers that Julius has been married before, and had never gotten a legal divorce.
When Chris is given the task of memorizing the longest presidential inaugural address and reciting it in front of the class as a punishment, he cooks up a surprising way of postponing his presentation. Meanwhile, Rochelle has problems of her own when a customer puts a hex on her.
It's the last week of school and while Drew decides he wants to try out for Amateur Night at the Apollo even without a talent at his disposal, Chris is informed that if he gets one more tardy he will have to repeat the 10th grade. But one day he misses the bus and arrives at school late, forcing him to deliver the bad news to his parents.