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.

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.

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.

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 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.

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.

Cliff and Clair are overjoyed with the arrivial of the new school year, as their children are finally out of the house.

Denise wants to buy a car. She plans to use her savings to do so, but Cliff and Clair quickly point out flaws in her plan. The answer to everyone's problems comes from friend Mr. Lucas, who has an old car he is willing to sell. Denise proves herself a good driver, and the car is hers. David Langston Smyrl as Mr. Lucas.

Clair bids on a painting by her great-uncle that her grandmother had once owned. Attempting to win her favor, Elvin tries to bake her a cake but fails miserably; he then gets advice from Cliff on how to pass himself off as a good cook. In real life, the painting used in the episode is Funeral Procession by Ellis Wilson.

Theo and his friend Cockroach scheme to pass a test on William Shakespeare's "Macbeth", which neither one has read.

After an exhausting midnight shift at the hospital and a night's sleep, all Cliff wants is to read his paper in peace - but the children have taken over every room in the house. Classic scene: Denise's boyfriend sings reggae in front of the living room TV.

Vanessa steals a sweater from Denise. The two soon begin to fight. In the end, Rudy's choice of television viewing, the "I Have A Dream" speech, reminds the whole family of what a real problem is. Excerpt from Martin Luther King, Jr.'s "I Have a Dream" speech featured at the end of the episode (Originally aired four days before the first observance of Martin Luther King, Jr. Day as a U.S. federal holiday).

Theo's math teacher has a baby and Cockroach shows a different side. Carl Anthony Payne II as Cockroach. Sonia Braga as Mrs. Westlake. Cockroach's full real name, Walter Bradley, is revealed in this episode (only his first name was previously mentioned).

Vanessa has a crush on a one Robert Forman, who comes to her Halloween party. Daydreaming about her love, she drops an entire tray of glasses and embarrasses herself in front of the guests. Pam Potillo as Janet. Dondre Whitfield as Robert. Akili Prince as Scott. (Years later, Prince would originate the role of Terrence Frye on All My Children. Upon leaving that series, he was replaced by Whitfield.)

While preparing to go out on a proposal anniversary dinner, Clair breaks her toe, but tries not to let it upset her routine. In the end, she develops a unique piece of footwear to hide her cast.

In a charity run, Cliff races at the Penn Relays with "Tailwind" Turner and -- as apparent payback for the race a year prior -- ends up having to run the final leg against Olympic gold medalist Valerie Brisco-Hooks. Josh Culbreath as Col. Sanford "Tailwind" Turner. Valerie Brisco-Hooks appears as herself. Cameo appearance by Bill Cosby's real wife, Camille Cosby (uncredited).

A close friend of Cliff's, played by Samuel E. Wright, is overcome with sadness due to his daughter's recurring drug addiction. His feelings are set off as he observes the close relationship between Cliff, Clair, and Denise, who is his daughter's age.

Rudy plays football and becomes a star, much to the chagrin of Clair, who worries she'll get hurt. But reluctance turns to excitement when Rudy is the star of her first game. Ethel Ayler as Carrie Hanks. Peter Costa as Peter.

Clair's sister Sarah gets engaged. First appearance of Joe Williams as Clair's father Al Hanks. Ethel Ayler as Carrie Hanks. Mario Van Peebles as Garvin.

After much deliberation, Denise chooses the college that she will attend in the fall. Earle Hyman as Russell. Clarice Taylor as Anna.

Russell plays in a tribute with the band he played in years ago. Guest appearances by jazz musicians Tito Puente, Art Blakey, Percy Heath, Jimmy Heath, Tommy Flanagan, Eric Gale, Joe Wilder, Carlos Valdes ("Patato"), Bootsie Barnes, and Jimmy Oliver. Slide Hampton provided the audio track for Russell's trombone solos.