In this special two-hour reunion, members of the cast, crew, recurring guest stars, and other influential people discuss the impact that The Cosby Show had on their lives. They also discuss the way that the show changed people's views on African Americans in today's culture.
Vanessa shocks Cliff and Clair by bringing home her fiance, Dabnis, who she has been engaged to for six months without telling either of them. Cliff and Clair are not happy at all, but reluctantly invite him to dinner. Clair believes that Vanessa is in over her head, but Vanessa insists that she's in love. Cliff doesn't like Dabnis, but he changes his mind when he discovers that Dabnis owns his own home, which means that Vanessa wouldn't have to live at the Huxtable house anymore.
Clair is surprised when Cliff shows her plans to add on a soundproof room to the house where she can escape the children. Cliff and Clair have co-signed a loan for Sondra and Elvin to get their first home. They sell their apartment, and are set to move, but then the couple that is selling the house that they want to buy files for divorce, complicating the sell, and in the process, leaving Sondra and Elvin homeless. They beg Cliff and Clair to let them and the twins stay in Martin and Denise's room while they are away in Japan, and when Cliff agrees, he forgets about the idea of adding on the room for Clair because he feels like he will never be able to escape the children. So instead of building the addition, they decide to build on an addition to the kitchen.
While in a parent-teacher conference, Theo develops a mutual attraction with one of his student's parent. When she invites him out for coffee, he declines stating that it wouldn't be in the best interest for the child. Theo is shocked, however, when he explains to Clair what happened, and she tells him that her clients hit on her all the time. Meanwhile, a boy named Stanley, who Rudy meets at the open house, is instantly smitten with her. So he can ask her out, he gets Rudy's phone number from Theo. But when Kenny hears about this, he gets jealous and hopes to sabotage their date.
Pam applies to all of the same colleges as Charmaine in the hopes that they will be able to stay together. But Pam, Charmaine, and her guidance counselor all have their doubts that her grades are up to par with the college's academic standards. Pam then decides that if she doesn't get accepted to any of those colleges, she will move back to California with her mother to study fashion design.
In order to go to a club called The Exchange, and possibly win a dance with JT Freeze, Rudy tells Cliff and Clair that she is going to a Bible study, and makes no mention that you are supposed to be over 16 to get in. When Cliff and Clair learn of her deception from Lance, Charmaine, and Pam, they send them to spy on Rudy in disguises. As luck would have it, Pam wins the dance with JT Freeze, and when she introduces him to Rudy and her friends, they freeze up making fools of themselves. In the end, Rudy has to work at a retirement home as her punishment, while Lance, Pam, and Charmaine are off partying at JT's hotel.
Cliff and Clair start to get annoyed by Sondra and Elvin always letting the twins run around the house and mess it up. But every time they try to put a stop to the situation, Sondra and Elvin use the twins to put a guilt trip on them. When Cliff learns that Sondra and Elvin won't be able to move into their house for another sixty days, he tries to get Russell to take them in for a little while, but he refuses.
When Russell finds out about Vanessa's engagement through a friend, who wrongly reports that Dabnis is 45, he and Clair's mother, Carrie, storm over and grill Dabnis in an outrage while they are visiting. Dabnis clears up the issue of age by telling them that Russell's friend always gets him and his older brother mixed up. Nothing he can do seems to earn their approval until Carrie and Russell see Dabnis give Cliff help on the housework. Even after Dabnis earns their seal of approval, Vanessa panics when they ask about the wedding date.
Cliff and his neighbor, Jeffrey, chaperon Olivia and her classmates on a field trip. Meanwhile, Theo decides to put messages on T-Shirts and sell them at street fairs as a fundraiser for the community center, but is upset after he thinks that he got a great deal on the shirts, just to discover that they don't have neck holes. Theo plans on taking care of the situation by himself, but Clair steps in to work things out.
After Theo convinces Cliff to teach a class for men only at the community center, the students misinterpret his intentions when Cliff brings Olivia's doll to the class by thinking that he will teach on sex education. The conversation eventually gets turned around to the young teen boys who are already fathers, and want to support their children, but don't want to get stuck with minimum wage jobs where they are treated like garbage. In the end, Cliff helps them all to get jobs. Meanwhile, while babysitting for Olivia and one of her friends, Russell becomes hooked on a video game.
While Miriam Makeba, a famous singer, is over visiting at the Huxtable house, Olivia disappeared. Everyone begins to search the house frantically for her, but Miriam is eventually the one who finds her hiding in a closet. Olivia explains that she is hiding to try to keep Martin from leaving. Miriam convinces her of how lucky she is to have such a big family that cares about her, and Olivia decides to come back to the party.
Dabnis confronts Vanessa about her being reluctant to set a wedding date after she runs home to Cliff and Clair's house. Dabnis wonders why she is pushing him away when she was the one to pursue him in the first place. In the end, Vanessa apologizes and asks Dabnis to be patient with her while she is trying to figure out exactly what she wants. Meanwhile, Kenny consoles Rudy after her break-up with Stanley by hanging around the house all day. Kenny is surprised when Stanley shows up and claims that he will win Rudy back, and uses Kenny's exact words about friendship and caring to patch things up between him and Rudy. Also, Cliff gets on Clair's nerves by revealing hints to the end of a book that Clair is reading.
Pam, Rudy, and Olivia become depressed when Clair spends the whole day in her new room after Cliff surprises her by finishing it early. The girls initially claim that they need Clair's help to bake the Christmas cookies, but then admit that the cookies are just more fun to make with Clair. Meanwhile, when Cliff tries to pass off the "tradition" of hanging the Christmas lights on Theo, Cliff leaves him bewildered.
After Theo gets accepted to graduate school, Cliff and Clair are ecstatic and agree to continue to pay his tuition. Later, Theo and a friend go to a corporation's recruiting dinner just so they can fill up on free food, but a surprise comes when Theo is offered a job interview by an executive who likes his off-hand comments about the company's philosophy. Theo is excited to tell Cliff and Clair that if he takes the job, it would pay $30,000.00 a year, and he wouldn't have to sponge off of them anymore. Things get a little bit complicated when a kid at the community center, Eugene, hears about this and thinks that Theo is leaving them. But Theo convinces him that he is just trying to keep his options open. Meanwhile, Clair gets tired of Cliff's habit of stealing the remote while she is watching a program, so she decides to put a stop to it.
Pam's old babysitter, Mrs. Whitaker, decides to bring some of her friends along with her on her weekly trip to the market with Pam on Saturday. Once they get back, Mrs. Whitaker and her friends decide to start a protest against a company that owns two markets that sell different things. One of them sells high quality food for low prices, while the other sells poor quality food for high prices. They feel that it's unfair to make some people who can't drive to the better market pay high prices for bad food. Their first plan of attack is to buy all of the dented cans from one market and return them to the other, but their plan fails when the markets hear about this and prepare for it. They then decide to pay for everything with pennies which seems to be effective. In the end, Pam decides to continue driving Mrs. Whitaker and her friends to the market every Saturday so that they can pay with their pennies until something happens.
While Pam fills in for Dr. Huxtable's assistant on a Saturday, one of his patients, Mrs. Minnifield, ends up giving birth in a cab after she ignores his instructions and heads for the hospital too late. Meanwhile, Rudy becomes jealous when Kenny shows up with a girl named Deirdre to work on a group project with her and Stanley. But Rudy soon stops being jealous when she feels that Kenny made up the whole thing just to try and get to her. Kenny begins to feel bad after he learns that Deirdre has actually liked him for a long time. He eventually convinces both Rudy and Deirdre to forgive him, and they agree to go on double dates sometime.
While Clair is away at a law conference in Washington, D.C., everyone is expecting him to follow in his normal path of pigging-out on junk food. Cliff surprises them though by eating very healthy meals. Meanwhile, when Rudy, Susan, and Danielle find out that everyone is taking a cab instead of being driven by their parents to the school dance, they decide they want to stand out by taking the subway. But Cliff won't allow this until Pam and Charmaine agree to ride both ways with them while they are seeing a movie. After they leave, Sondra stops by to check on Cliff just as a delivery man shows up with pizza, buffalo wings, and ice cream. He's still intent on eating the fatty food until he receives a call from Clair and she talks to him about trust causing him to feel guilty.
While Sondra and Elvin are moving into their new house in New Jersey, they ask Cliff to watch the twins. Cliff ends up breaking the grandfather clock in the living room while playing hide-and-seek with the twins after they wouldn't let him take a nap. The movers save Cliff by having the clock sent to a repair shop when they arrive and see what happened. When Elvin returns for the twins, he tries to talk Cliff into letting him buy his old station wagon since they will be needing one anyway.
Sondra and Elvin are excited as they prepare for their housewarming party, but are upset when they have to move it to the Huxtable house because of a faulty furnace. This of course doesn't make Cliff happy, but he cheers up when Russell comes over to report that Dabnis and Vanessa have set a wedding date. However, Cliff and Clair soon learn from Vanessa that it was just a rumor, and that they have actually broken up. They beg Cliff and Clair to keep it a secret at the party which causes many uncomfortable moments. Vanessa confesses that she just isn't ready to get married, but Dabnis explains that he wishes that Vanessa would just say what she's feeling instead of talking in twisted metaphors.
Cliff is happy when Theo decides to decline the job offer and go to graduate school because he didn't want Theo to move so far away. Later, at the community center, Eugene finds a wallet that has $600 in it. Eugene really wants to keep the money because his family needs it, but Theo lets the kids have a debate on what they should do with the money, and they decide that the right thing to do would be to give it back to the owner making Theo very proud. Meanwhile, Olivia and Marlon are writing a paper for school on what Cliff was like at their age. After they find out that all the stories Cliff had been telling them were really lies, they decide to call Russell up to get the real story. Cliff eventually impresses them by telling them a true story of how he got his picture in the newspaper by collecting tin foil for the war effort during World War II.
Clair plans a retirement dinner for her old college philosophy professor, Professor Capel, with a few of her college friends. They remember Professor Capel as a woman who was stimulating and extremely challenging, but also had extremely high expectations for all of her students. The women remember Professor Capel convincing them to take part and stick it out in a protest against a lunch counter that would not serve to blacks, but then she told the substitute teacher to fail them for missing class that day. Meanwhile, Olivia and Winnie convince Cliff that he needs to get a touch-up at their imaginary salon while they are having a sleepover. Also, Cliff doesn't like the exchange student that Vanessa brings home that can barely speak English because he is still trying to forget Dabnis.
Cliff and Clair suggest that Sondra and Elvin look to someone else when they inform Cliff and Clair that they are in the running to become the twins' legal guardians in case Sondra or Elvin passes away. They then turn to Theo, but become concerned by the fact that he's still in school, and the fact that their assets do not leave Theo enough money to support the kids. Meanwhile, Cliff has a talk with Rudy after she becomes moody and gets her to admit that she still does love her parents, even though they do bore her sometimes.
Cliff is excited about getting a chance to meet some of his favorite musicians when he and Clair got to a radio station live performance which is part of the Pan-American Music Festival. Meanwhile, Kenny has problems when he babysits Olivia, and she eventually leaves him so worn out that he can hardly stay awake. Later, Theo comes over to check on things, and after he sends Kenny home, he ends up falling asleep on the couch.
Cliff is upset that he can't claim most of the people that have lived in his house on his taxes. Sondra and Elvin have their own income, Denise and Martin have claimed Olivia, and Clair doesn't want to claim Pam, even though they can because she says that she wouldn't feel right about it. Meanwhile, Kenny throws a rushed birthday party together for Deirdre after he comes to the realization that socks aren't a good birthday present. Deirdre figures out what Kenny did and dumps him. Rudy convinces Stanley to talk to Deirdre on Kenny's behalf, who agrees to take Kenny back, but only if he stops lying and will take "boyfriend lessons" from Stanley.
In this first part of the two part series finale, Theo prepares to graduate from college, and even though each graduate is only supposed to get two tickets, he manages to get ten extras. Vanessa shows up with Dabnis, who she's bringing as her guest, but claims that they are only friends. Olivia gets ready to move to Singapore to live with Martin and Denise, and as a graduation present, Theo will be going with her. Theo has been worried by the way that Cliff has been acting, but Clair reassures him that she and Cliff are only very proud to see their son that used to struggle in school finally graduate.
In the second part of the two part series finale of The Cosby Show, a lot of things are happening. Denise surprises everyone by calling to announce that she's pregnant. Everyone is confused when Vanessa calls Dabnis "honey." While the ceremony is beginning, Cliff remembers back to the times when he thought that Theo would never graduate, but then becomes upset to learn that the students graduate by section instead of their names getting called out individually. That night, when Cliff and Clair have the house to themselves, they remember all the good times they've had, then the episode closes with them sharing a dance.