/ Dictionary / Index H high roller: Meaning and Definition of Find definitions for: high' roll'er Pronunciation: [key] — Informal. Informal. a person who gambles for large stakes, as in a casino. a person who spends money freely for entertainment and extravagant living. a corporation or governmental agency that invests or spends freely or recklessly. Random House Unabridged Dictionary, Copyright © 1997, by Random House, Inc., on Infoplease. highroad high-rolling Related Content Daily Word Quiz: immense Analogy of the Day: Today’s Analogy Spelling Bee: Today’s Spelling Bee Frequently Misspelled Words Frequently Mispronounced Words Easily Confused Words Writing & Language