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When can I use superlatives like наилучший instead of the word самый?

If I had to guess I'd say that the former is slightly more bookish but I'm not really sure. Usually I'd just use something like самый лучший. So the question is: which variant is more commonly used in everyday speech?

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    Thanks! It is advisable, though, to wait for 24 hours before accepting an answer so that other people have their chance at giving a better answer.
    – Alexander
    Mar 30 '18 at 17:21
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    besides самый there's also наиболее, it's a softer superlative operator, also bookish, but just as superlatives with the prefix наи- is used in educated speech Mar 30 '18 at 18:04
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First of all, "наи-" adjectives are indeed poetic or bookish. "Самый ..." is not only more broadly used, it's virtually always the safe choice.

This prefix can be used with adjectives that are in superlative form and can be applied to a human "наилучший"/"the best" , "наимудрейший"/"the most wise". Adjectives that normally can't be applied to a human (like "наимягчайший"/"the softest", "наисложнейший"/"the most difficult") are seeing even more rare use, and I wouldn't advise a non-fluent speaker to ever use those.

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