/ Dictionary / Index S silly season: Meaning and Definition of Find definitions for: sil'ly sea"son Pronunciation: [key] a time of year, usually in midsummer or during a holiday period, characterized by exaggerated news stories, frivolous entertainments, outlandish publicity stunts, etc.: The new movie reminds us that the silly season is here. Random House Unabridged Dictionary, Copyright © 1997, by Random House, Inc., on Infoplease. Silly Putty silly-sider Related Content Daily Word Quiz: paradox Analogy of the Day: Today’s Analogy Spelling Bee: Today’s Spelling Bee Frequently Misspelled Words Frequently Mispronounced Words Easily Confused Words Writing & Language