Crossword clues for the word: TRAILBOSS The word TRAILBOSS has appeared as an answer to at least 6 crossword clues on different crossword puzzles. Crossword clues for TRAILBOSS Showing 1 to 6 of 6 results Clue(s) "Curly's job in ""City Slickers""" Cattle drive leader Cattle drive VIP Driver on a range Head herdsman Head out West?