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a. His jokes were not funny at first and then they became even more not funny.

Is (a) grammatically correct?

It makes sense. I am not sure one could use 'less funny' here, because they were not funny at all at first.

On the other hand 'more not funny' doesn't seem grammatical to me, at least as far as formal English is concerned.

I suppose 'unfunny' would work in formal English. However, it seems to me that (a) is acceptable in informal English.

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    His jokes weren't funny to start with, and then they got worse. Commented Feb 15, 2022 at 8:14
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    Even more not is a very clumsy construction; it's logical to replace it with even less. Even more unfunny might be acceptable in informal conversation. Commented Feb 15, 2022 at 9:19
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    The use of "more not funny" is, in itself, amusing since it's such a clumsy way of expressing the idea. Commented Feb 15, 2022 at 10:32

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If the jokes were funny to begin with, you could have said:

His jokes became less funny.

But, in your example, I appreciate that they are not funny to begin with, and you can't get 'less funny' than not funny.

"Unfunny" is a great word, as it doesn't just mean something that is serious - it is defined in one dictionary as "anything that is designed to be found funny and fails", so you could say they became "more unfunny" if the jokes continue to fall further from the mark of what might be funny.

We also describe a joke that fails as "a bad joke", so you could say:

His jokes started bad and got worse.

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