This essay wades into the controversy surrounding Jon Stewart’s The Daily Show. Although some scholars have pointed up its constructive impact, others find it a harbinger of cynicism, superficiality, and excessive partisanship. This study offers a content analysis of Daily Show transcripts focused on social protest, and of a philosophical interview with Jon Stewart conducted by Rolling Stone magazine. Results show Stewart avoiding traditional forms of ideology, featuring desultory politics, stressing personal over group interactions, and embracing several dialectical choices—ideas vs. behavior, politicians vs. the electorate, and comedians vs. reporters. When the data are viewed as a whole, Stewart’s all-seeing, all-knowing rhetoric is identified as problematic, as is his lonely model of public life. Both make it hard to hold out hope for political solutions and that seems especially true for young people. While none of the foregoing claims can be considered definitive, they present new questions about The Daily Show’s impact on our life and times.