This chapter investigates the impact of restrictive regulations on artistic expression, focusing on musicians who address political and developmental issues. The study pursues three main objectives: (1) analysing how musicians use satire and parody to articulate their artistic voices within political contexts; (2) examining the chilling effects that fears of legal and privacy harms especially from politically sensitive songs have on musicians’ creative freedom; and (3) assessing how artists communicate the existence and consequences of such chilling effects. To achieve these aims, the research employs content analysis of song lyrics, performances, and related media, complemented by interviews with musicians and other stakeholders to provide in-depth perspectives. The chilling effect theory serves as the analytical framework, illustrating how fears of abduction and imprisonment influence artists’ creative decisions. Findings reveal that more than ten current regulations restrict artists’ and journalists’ ability to access or perform works critical of the government, resulting in widespread self-censorship and, in extreme cases, forcing artists into hiding for safety. Additional chilling effects include government bans on controversial songs, denial of opportunities for artists to participate in commercial advertisements, and the prevention of their songs from being broadcast on radio and television. Furthermore, artists who criticise the government often experience social isolation, as friends and associates distance themselves out of fear. These chilling effects suppress creative freedom and have broader social ramifications, impacting families and even government officials who may become indirect targets. In response, the government and prominent stakeholders in the arts sector are collaborating to reform colonial-era laws, aiming to ease these restrictions and foster an environment where artists can contribute meaningfully to democracy and national development.