New York Public Library (NYPL) has embarked on a program to build an open database of the performing arts called Ensemble. Volunteers are transcribing theater playbills from the NYPL’s collection. As part of the program, 200 theater playbills from 1911-1922 have been transcribed and are available online. Each playbill has its own webpage that contains its metadata: show title, date, theater name and location, production staff, cast members, headliner, and advertisements. This project represents a preliminary investigation of what elements may be of greatest interest to researchers once the Ensemble database is available. Python was used to reveal the top headliners, shows, directors, playwrights, and advertisements contained within this set of playbills.