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Lollapuzzoola: A Fun and Fierce Crossword Tournament

By Suryadeepto Sengupta

Modified Dec 06, 2024, 12:44 AM ET

Lollapuzzoola (Source: Instagram)
Lollapuzzoola (Source: Instagram)

What Is Lollapuzzoola? The Origins of the Event

Established in 2008, Lollapuzzoola is a yearly crossword puzzle tournament that is held in New York City and now virtually as well. Founded by Brian Cimmet and Ryan Hecht, it is the second-largest tournament held in America and one of the only major ones to be held in New York City. The name, Lollapuzzoola, was created by Amanda Yesnowitz, who used the Lollapalooza music festival as inspiration.

The tournament struggled to gain popularity for the first few years it was active but by 2011, things changed as Lollapuzzoola started gaining traction with more and more competitors taking part. So much so, that the tournament moved location to fit the growing number of players and they now even have a virtual tournament held alongside the in-person one.  

A Unique Crossword Tournament Experience

While the American Crossword Puzzle Tournament (ACPT) is considered to be the largest crossword tournament in America, Lollapuzzoola is a close second as it is one of the largest events held in the US. Unlike the ACPT, Lollapuzzoola is more known for its relaxed environment where a host of constructors, solvers, and crossword enthusiasts congregate.

The event has six puzzles for competitors to solve that are created by some of the world’s top constructors with the fourth puzzle often considered to be the hardest to solve. Even then despite being a tournament, Lollapuzzoola has a relaxed atmosphere with many treating it as a social gathering rather than a competitive tournament. Not only that, the puzzles are usually very unconventional as the creators created Lollapuzzoola to counter the ACPT’s traditional format.

The tournament is held in-person but ever since the COVID-19 pandemic, a virtual online tournament has been held simultaneously as well.

How to Participate in Lollapuzzoola

Held annually in New York City, Lollapuzzoola tends to attract hundreds of crossword solvers and constructors alongside regular fans every year. That combined with its relaxed vibe and offbeat puzzles created by renowned constructors has seen the tournament’s popularity grow year-on-year. So much so, that it is now one of the largest events of its kind, with only the ACPT attracting a larger audience in the United States.

That being said, here’s how to participate in Lollapuzzoola:

  1. Register online through the event’s website (bemoresmarter.com).

  2. The tournament is usually held in August on a Saturday and registrations are based on a first-come first basis so ensure you’re on time to register.

  3. Choose between in-person attendance in New York City or virtual.

  4. Arrive early on the day to check-in, socialize with other constructors and solvers, and even warm up before the event starts if you participate in person.

Lollapuzzoola’s Impact on the Crossword Community

Founded by Brian Cimmet and Ryan Hecht in 2008, Lollapuzzoola has now turned into one of the largest crossword puzzle tournaments in America and even in the world. While not the largest, the tournament is widely considered to be the second largest in America, behind only the ACPT. But Lollapuzzoola’s influence goes well beyond that as it has proved to be the opposite of what the ACPT traditionally stands for.

Its offbeat but engaging and challenging crossword puzzles, created only for the tournament, combined with the tournament’s relaxed atmosphere, have influenced tournaments worldwide. Not only that, it has become a breeding ground for new solvers, with many of them often going on to thrive in the ACPT, like Dan Feyer and Erik Agard. Lollapuzzoola also serves as a platform for many new constructors and solvers, giving them a chance to enjoy a tournament without the pressure of a major event.

So much so, that even though Lollapuzzoola is only a one-day event, the tournament’s impact goes well beyond that with Brooke Husic’s 4th puzzle of the 14th annual tournament still talked about to date.

What Makes Lollapuzzoola Special

Created to be the quirky opposite of the more traditional ACPT, Lollapuzzoola stands out automatically because of that but over the years it has become a lot more innovative. The tournament pushes players, constructors, and even regular fans outside their comfort zones by combining offbeat puzzles with a relaxed atmosphere. That has been the theme ever since the first Lollapuzzoola was held in 2008 and even now, 17 years later, the trend has continued.

The puzzles play a key role in that as they’re crafted by some of the best constructors in the world and very often include unconventional themes and mechanics. A big example of that is Brooke Husic’s 4th puzzle of the 14th annual tournament, which was held virtually. She took advantage of that and fooled many solvers with a uniquely creative crossword format. Other examples have tasked solvers to pass notes, use colored markers, or even meow aloud to get their answers.

That is on theme with the entire tournament’s vibe as Lollapuzzoola often features things outside the crossword tournament including trivia games, kazoo performances, and more. This has made it a special event on the annual calendar for many especially now that it’s held both virtually and in-person.

Winning Lollapuzzoola: Tips from Past Competitors

Even though Lollapuzzoola embodies a relaxed atmosphere with quirky and offbeat crossword puzzles, at its heart, it is still a crossword puzzle tournament and that shows. The event has six puzzles for competitors to solve that are created by some of the world’s top constructors with the fourth puzzle often considered the hardest and has stumped even some of the best solvers. But there are different divisions for players to compete in and each division has its own challenge level, which allows players to take things at their own pace.

That being said, here are a few tips from past competitors:

  • Practice a lot, especially with a variety of crossword styles from constructors known to be creative and/or ones that use offbeat clues.

  • Ensure your pop culture knowledge is up to the mark as Lollapuzzoola puzzles often incorporate said knowledge into their clues and themes.

  • Stay calm and level-headed as Lollapuzzoola is known for its challenging puzzles and confusing clues.

  • Embrace the atmosphere and enjoy yourself; with many past winners revealing that their success was down to that.

  • Use “Google Tickets” strategically as they can help overcome tough spots.