Mental Challenges Through the Ages

Your conception of reality usually relies greatly on your ability to comprehend a simple puzzle presented to you as a brief situation. Sometimes your response to such situations will affect your Intelligence Quotient; other times it will just make you sleepy. Either way, exercising as much of your brainpower as is possible without the use of medication or oral sex can never hurt. So, here are some riddles that challenge your existential awareness (the answers are negotiable).

First, a few for beginners.

Two men appear in the same scene of a movie. One wears a derby on his head. Where does the other wear a derby?

In digital technology, the speed in which bytes are buffered is determined by the strength of the stream sending the data. So what is the difference between DSL and LSD?

A woman paints herself yellow, walks naked in the rays of the Sun and yet is not noticed. Is she jaundiced?

Because of a rail-workers strike, no trains leave the station from noon until midnight and yet someone travels via rail at 1:24 p.m. and even has lunch in a dining car. Barring a possibility of time travel, what train does this someone take?

During a series of nine earthquake aftershocks, six people are purchasing Prada Candy Eau de Parfum. How many are female?

Any numbers of men engage in misogynist behavior at least twice a day, yet none have been involved with women. Have you ever kissed a homosexual?

If you cooked a steak in a pan at top speed, would you be cooking in an airplane or a canoe?

You are trapped against a wall on a Sunday afternoon because a few people are aiming loaded guns at you, threatening to empty the barrels of their guns into your body (note, anywhere on the body except parts covered by a vest). In what city is this taking place? (If you are further inspired by the question, describe the vest.)

A person is stupid. Name that person.

Next, some more complicated challenges. The first comes from ancient Greece.

Amaclamadees was a fake Greek philosopher. He was serious about being a philosopher for a few years before he developed a philosophy that being a philosopher was a total waste of time, as well as it paid poorly. When Amaclamadees quit being a philosopher due to his new philosophy, someone offered him many barrels full of drachma, the widely used currency of the time, to have his philosophy published. In need of money and craving a new wardrobe of tunics, Amaclamadees agreed.

The book he wrote contained many mental puzzles proving the meaninglessness of being a philosopher. Here are two.

Postulate one: A man stands between two columns in front of a building in Athens and spreads his arms full length. Each arm touches the columns on either side of him and he uses all of his strength to move them. When they do not budge he philosophizes by saying, “The weight of that which man creates with his own hands cannot be destroyed by his own hands.” That being true, why can one man destroy the thoughts of another man simply by behaving badly during sex?

Postulate two: Geometry sucks. Explain.

The next complicated mental challenge comes from the 20th century, when mental challenges began to become popular after years of being unpopular.

Two girls have the same mother but one girl has another father. How can one girl have two fathers?

A boat race includes five rowboats with only ten oars. How many people are in the boat that wins?

There are fourteen bald men at a private club for bald men. However, one of them is wearing a top hat. How do the other men know he is bald?

A weightlifter can press 456 pounds, which is twice his weight and twice that of what else in his life?

In a police station, there are a few people in jail that are behind bars. Does the police station serve liquor?

Three women are stranded on an island. How is it they can still shop for shoes?

Is a northern wind a wind that originates in the north or a wind that blows to the north?

A man throws a baseball and a bat swings at it. What is this scenario if not a game of baseball?

A despot is a dictator but not all dictators are despots. How many are there?

Written By

Known for his comedic acumen, Cotolo has made his living as a writer and a performer all of his life and during the lives of others. He is the author of the novel License to Skill and has co-authored its screenplay version, Molotov Memoirs, a collection of short stories. The Complete and Unabridged History of Japan, an epic novel, and a serious novella, Sweet Shephered. Frank Cotolo was born in Brooklyn and has worked in broadcasting, film, theater, music and television. He is currently the host of Cotolo Chronicles, one of the Internet’s first live broadcast radio shows.

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