Southwell early showed an intense desire to belong to the Society of Jesus, and, after a period of probation which he found almost intolerably long, succeeded in making his own way to Rome, where he was admitted to the novitiate at the age of seventeen.
1 Southwell, almost certainly, was a student at first hand of the Italian poetry which had been the origin of the conceits then common in English poetry; and the effort to express the eternal through the imagery of the temporal was one which his church, even in her liturgies, has always sanctioned.
Southwells mind is, naturally in his circumstances, much occupied with thoughts of sin, death and judgment; but he writes on these subjects with vividness and originality; and his intellectual force and religious passion make his treatment of them very different from the somewhat commonplace, or jaded, reflections which are to be found in the song-books.
Robert Southwell was brought up a Catholic, and at a very early age was sent to be educated at Douai, where he was the pupil in philosophy of a Jesuit of extraordinary austerity of life, the famous Leonard Lessius.
Father Southwell's prose elegy, "Triumphs over Death", was addressed to the earl to console him for this sister's premature death, and his "Hundred Meditations on the love of God", originally written for her use, were ultimately transcribed by another hand, to present to her daughter Lady Beauchamp.
Father Southwell's writings, both in prose and verse, were extremely popular with his contemporaries, and his religious pieces were sold openly by the booksellers though their authorship was known.