Fleming has written two books of legal humor, including Real Lawyers Do Change Their Briefs;[3] edited five other books, including three volumes of crossword puzzles;[4][5][6] and published a collection of crossword puzzles entitled I Swear.[7]
His crossword puzzles have appeared in the New York Times and many other newspapers; several magazines, including Games Magazine, The Rotarian, and The American Lawyer; and several books, including the Simon & Schuster Mega Crossword series and Random House Casual Crosswords; and in other venues. He appeared in the 2006 documentary Wordplay, which also featured a song that he wrote.[8] The New York Times crossword puzzle published on Friday, May 12, 2017, was collaboratively constructed by Fleming and former president Bill Clinton.[9]