The "Infinite monkey theorem" concerns itself with Probability (the mathematical field). It has been mathematically proven that given the random input (the mathematical kind - not the human-created kind) of the monkeys, and the infinite time, the probability of the "complete works of William Shakespeare" rolling out of the typewriter in between the other random output is 1
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It's a mathematical theorem that just uses monkeys to speak to the imagination, not a practical exercise, other than to prove the maths.
You should look into another brain-breaking probability problem called the "Monty Hall Problem". Note that some of the greatest mathematical minds of the time failed said puzzle. Switching 100% increases the chance of winning. No, it won't guarantee a win, but it will increase your chances, mathematically.
I have some weird news for you: Generations don't exist. Boomers? Not real. Silent Generation? Nope. Gen X? No! Millennial? Non-existent! ALL OF THEM.