Comparative and superlative adverbs?

I'm a native speaker of English, and I don't know how many times I've wanted to say "happilier" instead of "more happily", or "happiliest" instead of "most happily". Is there any record of such comparative/superlative adverbs (-lier, -liest) being used, even if it is in weird experimental literature?

Interesting problems arise with words already ending in "-ly", e.g.:

sillily: in a silly manner

sillilier: in a sillier manner

sillilily: in a manner suggesting a silly manner (double-adverb)

sillililiest: in a manner suggesting the silliest manner possible

(Typeset in fixed-width not because I think it's right, but because otherwise it's impossible to read "sillililiest".)

Answer

As far as your silly experiment, your problem arises in that ly is used to convert an adjective into an adverb, with the definition "in a [adjective] manner".

Thus, sillily is a word ("in a silly manner")

As far as "in a sillier manner", there are two rules for forming a superlative from an adverb. If the adverb was formed by adding ly to an adjective, you must use most or more.

"In a sillier manner" -> more sillily

"In the silliest manner" -> most sillily

If an adverb is the same as the adjective form, you can make a superlative using er or est

"In a faster manner" -> faster (ex. "He ran faster")

"In the fastest manner" -> fastest (ex. "He ran fastest")

As for sillilily, this is entirely nonsense. The reason is that our ly rule only applies to adjectives. You can not apply ly to an adverb and expect a "double adverb". An attempt to apply the rule directly would result in:

"In a sillily manner"

Notice that since manner is a noun, it should not have an adverb describing it. In your examples the word "suggesting" came out of nowhere. Nothing in the grammatical construction implied that there was suggestion.

In the case of sillililiest we encounter both of the above problems simultaneously. First, you attempted to make an adverb from an adverb by adding ly

sillily -> sillilily

Then you attempted to apply est or er to make a superlative

sillilily -> sillililiest

Both of these can not be done. The first because ly only applies to adjectives, not adverbs. The second because to make a superlative from an adverb which was formed by adding ly, you must use 'more' or 'most'. Again- you introduced the word "suggesting" which came out of nowhere.

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