/ Dictionary / Index G gentleman of the road: Meaning and Definition of Find definitions for: gen'tleman of the road' Pronunciation: [key] a highwayman. a tramp or hobo. Random House Unabridged Dictionary, Copyright © 1997, by Random House, Inc., on Infoplease. gentleman of fortune gentleman-pensioner Related Content Daily Word Quiz: stringent Analogy of the Day: Today’s Analogy Spelling Bee: Today’s Spelling Bee Frequently Misspelled Words Frequently Mispronounced Words Easily Confused Words Writing & Language