Crossword clues for the word: TOMDOOLEY The word TOMDOOLEY has appeared as an answer to at least 4 crossword clues on different crossword puzzles. Crossword clues for TOMDOOLEY Showing 1 to 4 of 4 results Clue(s) """Hang down your head"" guy in a Kingston Trio #1 hit" #1 hit for the Kingston Trio Folk song that was a #1 hit for the Kingston Trio Folk song that was a 1958 #1 hit