The work of Solomon Ibn Gabirol (Spain, 11th century), the most “modern” of medieval Hebrew poets is fascinating and multifaceted. He dedicated his short life, which was paved with misery and anguish, to poetry and in search of wisdom. Through his diverse works (poetry and prose), we will try to understand his contradictory personality and follow his philosophical viewpoint and his intellectual journeys. Special attention will be given to his personal poems in which he rose above the literary conventions of his time.