Freedom of speech is filled in various facets of daily life, which has long been the focus of people’s attention and debate. The concept has multiple layers, including mode, content, and timing of speech. It is worth noting that in different cultural, political and legal contexts, different groups of people interpret and apply freedom of speech in various ways. The purpose of this paper is to compare and analyze Austin’s Speech Act Theory, Ludwig Wittgenstein’s Language Game Theory and Hans-Georg Gadamer’s Hermeneutics. Also it aims to demonstrate and summarize three philosophers’ views on freedom of speech from multiple perspectives. By examining these philosophical frameworks, this paper attempts to guide people to further understand the factors that influence freedom of speech and clarify its inherent complexity. This paper not only provides a detailed analysis of the role of language in different contexts, but also provides a relatively complete model for understanding the dynamic interaction between language and society. In the era of globalization, the contradiction between the basic principle and practice of freedom of expression has become increasingly prominent. The results of the paper are intended to provide a reference for future efforts to strengthen intercultural dialogue to guarantee freedom of speech in pluralistic societies.