The theme of this study is gladness or joy, which, as Pope Benedict XVI stres- sed throughout his pontificate, is the distinctive trait of a Christian. Joy, however, can take on different shades and have various origins. Indeed, not every type of joy is Christian, and even within the history of Christianity, many authors, throu- gh their personal perspectives, have enriched the spiritual patrimony of the Church. This essay aims to systematize the concept of gladness in the work of Fr. Luigi Gius- sani (1922-2005), one of the twentieth century’s most original Catholic thinkers and educators. The word gladness is Giussani’s favorite to describe Christian joy. In the present essay, this term is confronted with similar words such as contentment, happiness, joy, peace, and tranquility, in order to grasp their similarities and pecu- liarities. The text then analyzes the genesis of gladness, particularly its relationship with faith, hope, and poverty, linking it to other experiences, such as freedom and chastity. The author hopes that this contribution will highlight the originality of Giussani’s thought and, at the same time, his profound fidelity to the Magisterium and the Great Tradition of the Church.