This chapter seeks to understand why hustling is such a prevalent theme in post-apartheid cultural production. It traces what Raymond Williams calls ‘structures of feeling’ – here, aspiration and frustration – back to the dissonant political economic vision of the ANC. As entry into the middle classes is repeatedly impeded for the poor by lack of structural change, so hustling becomes an ever more enticing mode of self-fashioning. But hustling can also be identified at the other end of the class spectrum, where white and black businessmen alike engage in nefarious practices in the pursuit of riches. Here I examine the stranger-than-fiction examples of Brett Kebble and Joe Modise. I connect the insights of novelists Niq Mhlongo and Carel van der Merwe to the findings of the Zondo Commission of Inquiry into state capture, which exposes the many ways in which corruption and fraud took place during Jacob Zuma’s presidency.