Key West Playbills Celebrates 20 Years of Connecting Local Businesses with the Arts

Key West Playbills, the advertising sales service that has grown from a single theater program into a cornerstone of the Florida Keys arts and business community celebrates its 20th anniversary this year.

Launched in 2006 by Key West resident Roberta DePiero, founder and president of Cocograms Enterprises, the venture began when DePiero was approached to sell ads for the Waterfront Playhouse program for a single season. What started as a one-year arrangement quickly expanded as Island Opera, Red Barn Theatre and Key West Symphony asked her to represent their programs as well.

The idea for a unified, multi-program service came directly from a client. After DePiero presented her with four separate programs to advertise in, the client told her, "This is great... I only have to see one person instead of four different people. Now if you could make all the programs the same size, it would cost me less to produce ads and I could support more."

Taking that feedback to heart, DePiero worked with Liz Young of the Florida Keys Council of the Arts to bring the theaters together and propose standardizing program sizes, a suggestion the organizations adopted.

From there, the business continued to grow. In 2011, Peter Arnow, then the driving force behind the Tennessee Williams Theater program, joined DePiero, and together they expanded the offering to eight programs. The following year, that number grew to 15, adding Nutcracker Key West, Music in Paradise, the Anne McKee Artists Fund Fine Art Auction, the Harry S. Truman Foundation, Summer Stage productions, Key West Fringe and the Key West Film Festival.

In 2023, Diane May joined the team to help promote Key West businesses alongside the theaters and events, bringing her sales and events background to the operation.

Today, as Key West Playbills enters the 2026–27 theater and event season, advertisers can reach audiences across 17 different programs through a single point of contact. 
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"We've seen arts organizations come and go over the years," DePiero said, "but we've always been there to help make each one’s season the best it can be. Peter, Diane and I are so happy to work in partnership with our clients and extend our thanks for two decades of creative collaboration!”