 Shortz was the first guest star the producers of The Simpsons approached . Long later asked Reagle to make puzzles for the episode . Reagle recorded his lines in a studio near his home . Reagle told the Arizona Daily Wildcat that " for me , to be such a total nut for animation since I was a kid , I never even dreamed [ of being in a cartoon ] . It 's like a dream I never had coming true . " He added that " you don 't see [ the crosswords ] in the episode for very long , but when crossword fans watch this show , we want them to think that we got it right . " Reagle designed every puzzle that appears in the episode , including one that appears in a hopscotch court in Lisa 's daydream . There were certain lines in the script that had to be incorporated into Reagle 's puzzles , including one where Gil says " I think I 'll throw some Q 's around , " , and he enters a number of Q 's onto the grid . Reagle therefore had to create a puzzle which used words that included the letter Q more frequently than would be usual . Reagle said he saw the early script of the episode , " but they change it right up to the last minute . In a lot of ways , I 'll be seeing it for the first time right along with everyone else . " Scott Thompson has a cameo in the episode as Grady , a character that he first voiced in the season 14 episode " Three Gays of the Condo " . 
