From '06 on, Will began lending his signature stylings to a completely different blockbuster series.
You may find the following chronology helpful:
2006: Will Shortz lies on his tummy to solve some puzzles.
2007: Will Shortz is a smiley face.
2008: Will Shortz places an apple on top of his puzzles.
2009: Will Shortz dares to put some letters on a checkerboard.
2010: Will Shortz eats some habaneros.
2011: Will Shortz carries a supreme pizza to his solvers.
2012: Will Shortz travels in a hot-air balloon.
2013: Will Shortz gives the OK to another pizza.
2014: Will Shortz dresses up as Uncle Sam.
2015: Will Shortz goes skiing.