This article draws out the significant similarities between the political insurgencies of Jesse Ventura in 1999 and Donald Trump in 2016, charting their own premillennial political collaborations as members of the Reform Party, before identifying wider lessons for studies of contemporary celebrity politicians through a comparison of their individual campaigns. Its analysis is based upon the concept of the ‘politainer’, introduced by Conley and Schultz, into which it incorporates Mikhail Bakhtin’s conception of the carnival fool. The heterodox nature of both Ventura and Trump’s political campaign styles, it argues, is in part explained by the nature of the cultural spheres within which their public personas were produced; specifically, the fact that these personas, which they carried over from the entertainment to political spheres, were produced within genres of popular culture generally positioned as having ‘low’ cultural value. This, it argues, furnished both with an anti-establishment ethos as ‘no bullshit’ straight-talkers, marking them as outsider candidates able to act as conduits for political protest by an electorate alienated from mainstream political elites. It concludes by emphasising the potential importance that political celebrities’ specific cultural production can play in shaping a subsequent political campaign in general.