Crossword clues for the word: DIERKSBENTLEY The word DIERKSBENTLEY has appeared as an answer to at least 2 crossword clues on different crossword puzzles. Crossword clues for DIERKSBENTLEY Showing 1 to 2 of 2 results Clue(s) "Drunk on a Plane" country singer who is a licensed pilot (2 wds.) Singer of 15-Across and 29-Across who was awarded the 2018 Academy of Country Music's Merle Haggard Spirit Award (2 wds.)