Crossword clues for the word: SILLIEST The word SILLIEST has appeared as an answer to at least 9 crossword clues on different crossword puzzles. Crossword clues for SILLIEST Showing 1 to 9 of 9 results Clue(s) "Most like a They Might Be Giants song, maybe" Least serious Most absurd. Most foolish Most goofy Most inane Most ridiculous Most slaphappy Reclines in muddy sediment, which is most ridiculous