This paper examines user-generated metadata as implemented and applied in two web services designed to share and organize digital media to better understand grassroots classification. Metadata - data about data - allows systems to collocate related information, and helps users find relevant information. The creation of metadata has generally been approached in two ways: professional creation and author creation. In libraries and other organizations, creating metadata, primarily in the form of catalog records, has traditionally been the domain of dedicated professionals working with complex, detailed rule sets and vocabularies. The primary problem with this approach is scalability and its impracticality for the vast amounts of content being produced and used, especially on the World Wide Web. The apparatus and tools built around professional cataloging systems are generally too complicated for anyone without specialized training and knowledge. A second approach is for metadata to be created by authors. The movement towards creator described documents was heralded by SGML, the WWW, and the Dublin Core Metadata Initiative. There are problems with this approach as well - often due to inadequate or inaccurate description, or outright deception. This paper examines a third approach: user-created metadata, where users of the documents and media create metadata for their own individual use that is also shared throughout a community.