/ Dictionary / Index H high-rolling: Meaning and Definition of Find definitions for: high-roll•ing Pronunciation: (hī'rō'ling), [key] — adj. Informal. gambling, spending, or living extravagantly or recklessly: high-rolling gamblers; a high-rolling investor. Random House Unabridged Dictionary, Copyright © 1997, by Random House, Inc., on Infoplease. high roller high school 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