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Essential Seven Greatest Cosby Show Episodes

Recently the entire series of The Cosby Story debuted on Netflix, and I have been reliving all of my favorite episodes. Ask anybody what their favorite episode was, and you will probably get multiple answers. Some enjoyed when the episodes where Bill Cosby would interact with Rudy and her friends. Others enjoyed the episodes that featured Dr. Huxtable and Theo discussing life. I always loved the food episodes. Dr. Huxtable’s love of hoagies (with apple juice!) is something that I can easily relate too. No matter what you loved about the show, there will always be a debate of what were the best episodes. If your scratching your brain on what episodes were the best here are the Essential Seven Greatest Cosby Show Episodes:

7) A Shirt Story

Theo wants to look good for his date, and buys a $95 Gordon Gartrelle designer shirt. Outraged by the price Cliff, insists that he return the shirt. Denise claims that she can make Theo an identical shirt for half of the money. The end result featured a screwed up collar, short puffy right arm sleeve, and a shirt that Theo tucks all the way into his socks.

6) I Know That You Know

Unable to trick Dr. Huxtable with joke gags, Cliff proclaims that no one could ever pull a joke on him. Shortly after Cliff heads to work, Sondra and Elvin arrive announcing their engagement. The family decides to play a prank on Dr. Huxtable since he hadn’t heard the news. When Cliff returns Elvin, pretends to fear that Clair will not support their engagement, and asks his advice on how to tell her. Thinking he knows his wife, Cliff believes there won’t be a problem. He was wrong. Clair pretends to hate the idea of Elvin and Sandra getting engaged. Later that day Cliff overhears the kids talking about the trick, Cliff turns the joke on them and pretends to throw Elvin out of the house.

5) Move It

Elvin and Sandra invite Cliff and Clair over to their apartment for dinner. When they get there they are disgusted by the brown tap water, jammed windows, and electrical problems. Clair immediately has Elvin call the landlord, who shows up after hearing that Clair is an attorney. Even the pigeon agrees the place is a dump!

4) I’m In With the In Crowd

At a party Vanessa and her friends play drinking games with a bottle of bourbon. After the game, Vanessa calls Denise to take her home. Discovering that their daughter is drunk, Cliff and Clair intend to teach her a lesson. They pretend to have a drinking game with Rudy.

3) Happy Anniversary

Cliff’s parents Russell and Anna celebrate their 49th anniversary with a dinner over at the house. The family present the couple with a painting of the them as newlyweds. Then the entertainment begins. The family performs Ray Charles’ “Night Time Is the Right Time”, with Theo, Rudy and Cliff each lip-synching a solo. The anniversary performances became a reoccurring episode every season. The first however was the best.

2) Planning Parenthood

Cliff takes Rudy and her friends to the Port-au-Prince restaurant for lunch. The kids don’t want to eat the duck face or the croutons on the salad. The gourmet hamburgers they order are huge beef patties on toast. Nothing like they are used too.  The kids don’t like the look of the food. The sympathetic waiter saves the day and runs across the street for burgers from the fast food restaurant Circus Burger. Every time I see this episode I crave a hamburger that looks like that.

1) Theo’s Holiday

The family grows tired of Theo owing them money. Cliff decides to teach Theo a lesson of what it will be like for him to live in the real world. The family converts the house into “The Real World Apartment Building.”  Cliff plays the landlord Harley Weedwax who rents Theo his own room. Playing along Theo brings in Cockroach to act as his employer and reference to obtain a “bank loan.” Sadly Theo can’t convice the loan officer Mrs. Griswald to approve.


The Essential Seven is a weekly list of seven items that we at MillionairePlayboy.com believe needs to be identified. Want our opinion on a topic for a future list? Email Lando Da Pimp. Don’t agree with our list? Then leave a comment. We will try not to laugh at your dumb opinion! 😉


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