After Theo claims that he'll have no problem making it in the "real world", the Huxtables convert their house in the "Real World Apartments" and teach him a lesson about the real world; i.e., needing employment and references to get an apartment, income to get a bank loan, having to pay for his meals, etc. Carl Anthony Payne II as Cockroach.

Theo wants to impress a girl by wearing an expensive shirt by designer Gordon Gartrelle. Since Cliff and Clair will not pay for it, Denise offers to make a copy of the shirt for him. Guest appearance by Kadeem Hardison, who years later would portray Dwayne Wayne on the Cosby Show spinoff, A Different World.

For Russell and Anna's 49th wedding anniversary, the family commissions a portrait of the couple as newlyweds, and offers them a cruise to Europe. Later in the evening, the whole family performs Ray Charles' "Night Time Is the Right Time", with Theo, Rudy and Cliff each lip-synching a solo. Earle Hyman as Russell. Clarice Taylor as Anna.

Vanessa and her friends sneak out of town to attend a concert in Baltimore, but encounter huge problems along the way. Afterwards, she must face the wrath of Cliff and an infuriated Clair.

Clair is furious when Theo brings home a report card with 4 D's. He tells Cliff that he has no intention of going to college, as he feels that he is destined to be a ""regular person."" Cliff uses Monopoly money to teach him about the economic realities that many blue-collar workers must face. He assures Theo that he only wants him to try his best. Cliff is alarmed to meet Denise's latest beau, a former merchant marine who once spent time in a Turkish prison.

Rudy invites all of her friends over for a slumber party. It's Cliff's job to watch over them, and he demonstrates some unique games to wrangle the youngsters. In the end, Russell drops by and demonstrates the perfect way to deal with kids-bribe them!

When Sondra and Elvin announce their engagement, Clair and the children use the news to play a practical joke on Cliff, who launches a counter-offensive of his own. Geoffrey Owens as Elvin.

Denise invites Martin's ex-wife Paula for Thanksgiving dinner. Clair continues to send Cliff to the store for last-minute groceries, despite the fact that it is a cold and rainy Thanksgiving Day. Victoria Rowell as Paula.

Theo gets his ear pierced to impress a girl, but Denise thinks it might be infected. She is correct, and Theo must go to Cliff. Cliff hopes that Grandpa Huxtable will punish Theo, but the old man instead relates the story of how Cliff tried to slick back his hair to impress Clair, but ended up burning it off! Russell brags, and Anna reminds him of the time that he had a tattoo of her name placed on his chest, but ended up with a huge scar on his chest when he tried to remove it after Anna found out he was actually trying to impress another girl! First appearance of Clarice Taylor as Anna Huxtable, Cliff's mother.

Cliff, who has a fetish for electronic appliances, buys a juicer. Rudy and Peter, bored from Vanessa's inattentive baby-sitting, decide to use it even they are not allowed to use appliances. David Langston Smyrl as Mr. Lucas. Peter Costa as Peter.

Cliff, Elvin and Martin secretly compete to determine who is the most romantic husband in the Huxtable family.

Sondra breaks up with her boyfriend Elvin and is depressed, taking it out on the family. Cliff and Clair aren't exactly unhappy; they find Elvin rather annoying. Later, he appears at the house with flowers and tries to apologize. While there, he offers some of his sexist rhetoric to Clair, who quickly becomes annoyed. First appearance of Geoffrey Owens as Elvin. Joseph C. Phillips appears as Daryl (Phillips joins the cast in Season 6 as Denise's new husband, Navy Lt. Martin Kendall)

Denise asks Cliff to talk to her friend, who has a medical problem. Cliff diagnoses the girl as having a mild bladder infection, but learns that she was wary of telling her parents without certainty. Cliff and Clair decide to show the kids that they can tell them anything, but the children quickly point out that their parents will just get angry. Cliff admits that anger is part of problems, but tells the children that no matter what, they will be loved.

Peter goes to the dentist, but has Rudy come along for moral support so Peter won't be afraid of the dentist anymore. Danny Kaye (in one of his last appearances) as Dr. Burns, who is also Cliff's dentist.

After his limo collides with Denise's car, Stevie Wonder (appearing as himself) invites the Huxtables to a recording session. Wonder performs "I Just Called to Say I Love You" with Clair and the family. Absent: Sabrina Le Beauf as Sondra Huxtable.

Cliff plays pinochle with his father, a former teacher, and a friend. Theo buys a cheap ring for his girlfriend Tanya. Earle Hyman as Russell. Roscoe Lee Browne as Dr. Foster.

When Rudy's pet fish, Lamont, dies, Cliff tries to bring the family together for a funeral in the bathroom. The festivities end when Rudy gets bored and leaves to watch TV.

Denise has a new boyfriend, David, but is reluctant to bring him home. She fears that Cliff will, like always, make fun of the boy and ruin her chances with him. Cliff and Clair are initially impressed with David until he expresses some unwanted opinions about medicine and the law at dinner. Kristoff St. John plays boyfriend David.

Clair discovers a marijuana joint in one of Theo's school books. She and Cliff confront him about it, and accept his explanation—another boy slipped it in. Theo confronts the boy and brings him home to confess in order to remove any uncertainty from his parents about his telling the truth. Theo and the boy actually start to become friends. Stephen Thompson as Anthony Braxton, Iman as Mrs. Montgomery. Rudy says her full name in this episode, Rudith Lillian Huxtable.

When friend Suzanne accompanies Denise to observe the Huxtables' normal behavior, a smitten Theo behaves far from normally. Robin Givens as Suzanne. Blair Underwood as Mark.

Denise returns from Africa, with a new husband and stepdaughter in tow. Joseph C. Phillips and Raven-Symoné join the cast as Martin and Olivia Kendall. Last appearance of Peter Costa as Peter.

Cliff tries to win a classic jazz record at an auction, while filling in for Denise as volunteer parent at Olivia's preschool. Sullivan Walker as Dr. James Harmon.

Cliff's father, Russell, pays a visit and begins questioning Cliff about the kids' college choices. He asks Denise about Hillman, his and Cliff's alma mater. Denise is dead-set against it at first, until Russell tells her that the males outnumber the females there. First appearance of Earle Hyman as Russell Huxtable, Cliff's father.

Cliff is turning 48, and as usual, he is trying to find out what his birthday present is ahead of time. Clair, with the help of the kids, orchestrates a huge trick. Cliff is fooled, and doesn't find about what is birthday surprise is: a visit to Lena Horne's private club. Lena Horne as herself, Clarence Williams III as Clarence Thornehill. In episode 12, Cliff says his birthday is in October.

Theo's math teacher comes for dinner, to Theo's extreme consternation. He thinks she plans to tell his parents of a bad grade on a math test. To his surprise, Mrs. Westlake comes to dinner looking young, attractive, and even with a sense of humor; and she has a very good surprise! Mrs. Westlake also gives Theo his test-he actually gets an 89, and he proceeds to embrace her, much to his shock. Sonia Braga as Mrs. Westlake.