Five signed notes to Mary Ann Madden, with a photograph. The earliest is an autograph note signed on Mr. Sondheim's stationery dated 23 March, thanking "MA" for an end table ("It's the end.") and a dinner ("It's the dinner."), signed "Love/Steve", with an envelope hand-addressed and signed in full "Stephen Sondheim" postmarked April 27th, 1964. This is followed by four typed notes on Mr. Sondheim's stationery, each signed "Steve" except one which is signed "Smiley," dated 1966-1984, the short notes with statements such as "Thanks for being around last week... Your frivolous behavior and dress were a consolation and shock to all." The letter signed "Smiley" closes with "XXXOOO (tic-tac-toe to you)." Usual folds, one letter with stain. The lot is accompanied by a copy of a color photograph depicting Mary Ann Madden with Stephen Sondheim.

In the late 1960s, Stephen Sondheim devised a weekly cryptic crossword puzzle for the back pages of New York Magazine, then in its first years of publication; finding it too time-consuming, he backed off to every three weeks and suggested his friend, the talented wordsmith Mary Ann Madden, provide content for the weeks in between. Ms. Madden created the popular wordplay New York Magazine Competition, in which players would at first mail and later email in responses. Ms. Madden created 973 competitions over a 32-year career at the magazine (the largest response was once 9000 postcards).