As substances often described as 'drugs of abuse', khat and cannabis are perceived negatively by many, including in East Africa where they have garnered much notoriety. However, these substances are not solely viewed through a 20th Century 'war on drugs' prism, and many in East Africa counter negative perceptions of them by arguing that they should be seen instead as bedrocks of rural agriculture and economies, and as items of traditional consumption unfairly tarnished by colonial laws. In such arguments, khat and cannabis are portrayed as 'respectable' substances of great potential value to society. Others - especially young consumers - appear to appreciate the reputation of these substances as not 'respectable' in genteel society, this lack of 'respectability' infusing them with an air of cool defiance and earning them a different sort of 'respect', one linked to global youth culture. This paper explores the different cultural resonances of these substances, how they have changed over time, and how they are changing in a present era where drug law is in a state of flux. In doing so, it shows the intricate ways in which perceptions of drugs are formed, and the complicated relationships between perspectives on these substances and drug law.