He obtained a degree in enigmatology, or the study of puzzles, by way of Indiana University's "Individualized Major Program." He then went on to obtain his Juris Doctor from the University of Virginia School of Law in 1977. He also holds an honorary Doctor of Human Letters degree from Wabash College in Indiana, that he received in 2010.
Shortz's career began at Penny Press Magazines, a notable crossword puzzle publisher before a 15 year stint at Games Magazine.
Since 1993, Shortz has been the crossword puzzle editor for The New York Times. He is also a regular guest on NPR's Weekend Edition Sunday, where he hosts the Sunday Puzzle.