The freedom of speech is expressly guaranteed in Article 14 of the Singapore 'Constitution' for every citizen of Singapore, but the courts have consistently eschewed a living tree approach to constitutional interpretation and have espoused the four walls doctrine that restricts the engagement with foreign and international sources of law that may inform or influence local constitutional interpretation. However, recent decisions of the highest appellate court in Singapore suggest that the sands are shifting. This article discusses the ambit of Article 14, and its vertical and horizontal applications. It concludes that in order for a fundamental constitutional right such as the freedom of speech to flourish, its interpretation needs to take into account changes in moral values, technological development and the evolving civic culture of modern Singapore.