Over the last 10 years, The Daily Show with Jon Stewart has produced over 10,000 segments. Creating an accessible web site to include an archive of this size presented quite a few challenges for the Comedy Central Information Architecture team. In addition to needing to take full advantage of the Web to carve overlapping trails for people to explore, it was also necessary to provide carefully curated paths within the design to allow users to create new connections on their own. Audrey Chen, the Senior Information Architect at Comedy Central, will explore her experiences with this considerable task. She will discuss how her IA team needed to re-examine every assumption they had about presenting content online, and some of the gems found along the way.