Ecclesiastes 2:1-3

1 I said in my heart, “Come now, I will test you with mirth; therefore enjoy pleasure”; but surely, this also was vanity.

² I said of laughter—“Madness!”; and of mirth, “What does it accomplish?”

³ I searched in my heart how to gratify my flesh with wine, while guiding my heart with wisdom, and how to lay hold on folly, till I might see what was good for the sons of men to do under heaven all the days of their lives.

enjoy (v.1) — totally enjoy

madness (v.2) = folly which results from loss of discernment

mirth (v.2) = thoughtful pleasure

“Under the heaven” (v.3) is the opposite of “under the sun.” The latter is living without regard to God or eternity, whereas the former is living with an awareness of Him and an understanding that this life is not all there is. — Grace, page 1169.

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The dissatisfaction and vexation of spirit which Solomon experienced in testing the insufficiency of industry, philosophy and pleasure, were the more painful because of his possession of the super-human wisdom which remained with him (v.9); for the greater the capacity of enjoyment the greater the disappointment and vexation. His misery was, therefore, greater than that of any who preceded or succeeded him, because of this unique gift of wisdom; and if ordinary intelligence finds everything “under the sun” to be vanity, extraordinary intelligence finds it to be “vanity of vanities.” — Williams, page 440.

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The splendors of Solomon’s court were known to all (cf. 1 Kings 5–10). The Preacher now recounts his attempts to find something of value or profit in the pursuit of those pleasures that the wealth of such a court afforded. He temporarily hung all of his inhibitions in the closet and entered into the pursuit of pleasure with zest. … He sought, literally searched out, the satisfaction that could be achieved by giving himself to wine. — KJV Commentary, page 738.

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Solomon is not speaking here (v.2) of a sober enjoyment of the things of this world, but of intemperate pleasure, whose two attendants, laughter and mirth, are introduced by a beautiful prosopopeia, as two persons, whom he treats with the utmost contempt. — Treasury, page 423

This almost reads like Solomon was checking items off a list as he attempted to find the meaning of life. Item next: wanton pleasures. But superficial fun (laughter) only led to madness, and a more reasoned pursuit of fun didn’t accomplish anything. Next he tried wine, but while he was doing all this, he wasn’t just a participant but also an observer. He analyzed the results of the pursuits of pleasure to see if any of them were worthwhile.