Lollapuzzoola

Anyone can participate. There are two skill divisions, a rookie division, a pairs division, and for those who can't attend in person, an at-home division. Prizes are awarded in all divisions, with trophies and cash/gift certificate prizes for the top winners in the two skill divisions. For the purposes of prizes contestants compete simultaneously in all divisions for which they are eligible, with no more than one cash prize per contestant.

L-R: Patrick Blindauer, Will
Shortz, and Brian Cimmet.

The tournament consists of five rounds, each with a puzzle that all competitors solve. There are three rounds in the morning and two in the early afternoon. Puzzles vary in size and difficulty from round to round. The puzzles are commissioned by the tournament directors from the top constructors in crosswords, with the fourth puzzle the hardest of the set. The puzzles vary in size, shape, and difficulty, although the first one is traditionally a relatively easy 15x15 grid. The puzzles are always themed, and frequently themed in off-center, wacky ways not commonly seen in newspaper-published crosswords. For example, puzzles have included a "Name That Tune" gimmick; a post-solve Twister game; a puzzle that instructs the solver to eat a Chips Ahoy cookie upon completion; and a puzzle that required the entire room of solvers to make noises from their chairs, and thus perform an impromptu rendition of John Cage's 4'33''. Judges score the solved puzzles on accuracy and speed.

After these five rounds, the top three solvers in the two skill divisions progress to the final round, which consists of solving a very difficult crossword on an oversize grid onstage at the front of the room. The competitors in this round wear noise-blocking headphones. The solvers hold a sheet of clues and write their answers on the grid with a dry-erase marker for all to see. The competitors are ranked by fewest mistakes, then time. The winner of this round is declared the champion. The top three competitors in the Express and Local divisions compete on the same puzzle with different sets of clues for their titles.

Four times during Lollapuzzoola's history, New York Times crossword editor Will Shortz purchased puzzles commissioned for the tournament for publication in the newspaper. On September 5, 2009, Mike Nothnagel's final puzzle from Lollapuzzoola 2 was published in the New York Times (see XWordInfo.com page). On August 20, 2011, Byron Walden's final puzzle from Lollapuzzoola 4 was published (see XWordInfo.com page).[12] On September 11, 2014, Patrick Blindauer's puzzle "Change of Heart" from Lollapuzzoola 7 was published (see XWordInfo.com page). On August 9, 2016, Andrea Carla Michaels's puzzle from Lollapuzzoola 4 was published in advance of the upcoming tournament, and (in part) as a promotion of Lollapuzzoola (see XWordInfo.com page). Each time, an additional block of text was added to the puzzle to tell solvers that this puzzle had appeared in a national tournament and to give information about the winner and their solving speed. In the case of Walden's puzzle, the byline was extended to include "edited by Brian Cimmet and Patrick Blindauer", the first and only instance of an editor besides Shortz since he began working for the Times.

As of 2023, there have been two repeat winners: Jeffrey Harris and Will Nediger. Past champions traditionally return in subsequent years as judges and/or constructors.

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