In a fresh wave of literary fun, we are re-launching the competition inspired by the celebrated New York Magazine Competition. This engaging competition, modeled after the legendary series created by Mary Ann Madden, promises to be an intellectual and creative delight for residents, blending humor, linguistic flair, and community spirit.
The competition challenges participants to showcase their cleverness through playful word games, puns, and inventive prompts. Madden’s original contest, which began in 1969 and captivated audiences for over three decades, was born out of a unique collaboration with Stephen Sondheim. Now, New Canaan residents will have the chance to carry on that same tradition of literary excellence.
The first challenge, “Awkward Introductions,” invited participants to craft humorous, inventive ways of introducing characters, real or imagined, in the most uncomfortable social situations. Whether through witty dialogue or clever descriptions, contestants are encouraged to unleash their creativity and compete for a chance to have their entries featured in print.
Throughout the year, the contest will offer a series of rotating themes, ensuring that participants—whether seasoned wordsmiths or casual writers—find opportunities to engage. As Mary Ann Madden’s competition drew literary heavyweights like David Mamet and Herb Sargent, New Canaan’s version aspires to foster a similar sense of community.
While the competition celebrates humor and cleverness, it also serves as a reminder of the power of language to connect, inspire, and entertain. Each round will reflect that spirit, encouraging residents to gather around the printed edition of the paper to enjoy the results.
Winners will see their entries published in the print and digital editions of The New Canaan Sentinel.
Now is the time for New Canaan residents to take up the challenge, whether by pen or keyboard, and make their mark. Prompts will range from playful word games to satirical poetry.
We invite everyone to participate and share their literary talents. Let your imagination run wild and join us in turning this competition into a cherished tradition.
