[4][5] Berry grew up in Boca Raton, Florida, and often solved Dell Magazines variety puzzles and tried to write his own crosswords in his youth.
[7][8] Berry continued writing puzzles for outlets such as The New Yorker, Harper's Magazine, and the American Crossword Federation's Tough Cryptics newsletter.
[6] He invented several variety puzzle formats, such as Rows Garden, Some Assembly Required, Boxing Rings, and Snake Charmer.
[10][13] He constructed a six-puzzle meta suite (a series of related puzzles) for the week of October 17, 2011, at the request of editor Will Shortz.
[14][15] He has regularly written variety puzzles for The Wall Street Journal and formerly edited the Chronicle of Higher Education crossword.