This paper chronicles the development of Drehort Neubrandenburg Online, an interactive, content-rich audiovisual language learning environment based on documentary film material shot on location in Neubrandenburg, Germany, in 1991 and 2002 and aimed at making language learning more interactive and more real. The paper starts with the description of the first film project and the struggle to make the linguistic material accessible to students learning German. It continues with a description of further development stages using emerging technologies--laserdisc and digitized media files, HyperCard, Libra, and internet applications such as Flash--describing which new tools are effective and for what reasons and what the use of technology may mean for language learning from a theoretical and from an empirical perspective. (Contains 3 figures.)