Since its inaugural conference in 2003, the Python community has hosted over 1200 talks, in over 30 countries, with more than 20,000 attendees in the U.S. alone. That’s a lot of Python -- and a lot of extractable data. By examining the categories and topics of seminar abstracts over the years, observations about the development of the language and the Python community's interests can be found. These insights are invaluable to understanding how both the community and language have grown, where they are headed, and how people may support the continued growth of Python for years to come. This year for the 15th anniversary of PyCon, we will highlight some of the many diverse presentations of previous conferences, piquing not only your nostalgia, but also your appreciation for the impact this event has on what is shaping to truly be a hundred-year language.