The New Yorker
Diffee has a background in art and stand-up comedy which he still performs from time to time. As a struggling artist he took various day jobs, including road work, construction, and as a convenience store cashier. Diffee moved from Boston, Massachusetts to New York and began contributing to the New Yorker in 1999, after winning a cartoon contest the magazine and the Algonquin Hotel sponsored. Diffee's first book, The Rejection Collection, was a compilation of cartoons by various artists that had been Diffee's first book, The Rejection Collection, was a compilation of cartoons by various artists that had been rejected from the magazine along with questionnaires and portraits of each artist. The New Yorker has published more than 100 of Diffee's cartoons.