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Answer for the clue "He sips any cocktail that's hard and fruitless ", 9 letters:
sisyphean

Alternative clues for the word sisyphean

Word definitions for sisyphean in dictionaries

The Collaborative International Dictionary Word definitions in The Collaborative International Dictionary
Sisyphean \Sis`y*phe"an\, a. Relating to Sisyphus; incessantly recurring; as, Sisyphean labors.

Douglas Harper's Etymology Dictionary Word definitions in Douglas Harper's Etymology Dictionary
"pertaining to or resembling the unceasingly recurring and fruitless labors of Sisyphus," 1630s, from Sisyphus + -an . Earlier Sisyphian (1590s).

Usage examples of sisyphean.

LCD stacking up a Sisyphean queue of unplugga-ble leaks, Kraft tends to stray into the contempt bred of familiarity.

Dan Rembert did a magnificent job with the book cover, and Lynn Anderson accomplished the Sisyphean task of copyediting my prose with such skill that she seems to have actually gotten the boulder over the hill.

Manticore's persistently better hardware had begun to assume Sisyphean proportions for Parnell, and it pleased him to see the Manties' faith in their technological superiority boomeranging on them.

In justice to Buddhism, let us not charge its Scripture with the Sisyphean task of seriously upholding the literal interpretation of obviously fantastic passages.