Michelangelo and Vittoria Colonna met sometime in the mid- to late 1530s when he was working on the Last Judgment and she was residing in a convent in Rome.1 Colonna and Michelangelo were friends who visited each other regularly, wrote often, and exchanged poems and drawings for almost a decade.2 The relationship between the two was rich, complex, long lasting, and deeply spiritual. This friendship also occasioned the creation of some remarkable works of art. It was for Colonna that Michelangelo produced drawings depicting the Pietà, the Crucifixion, and the Samaritan Woman, the last of which is now known only through printed copies.

Passing through the unassuming portal of Santa Maria degli Angeli, visitors soon enter a cavernous space. In many ways, the grand scale and ornate decoration of the interior that greets them is difficult to reconcile with the plain brick exterior. Worshippers and tourists alike often stop, gape, and then wander the space aimlessly. In contrast to nearly every other church in Rome, where the altar presents itself immediately opposite the entrance, the altar of Santa Maria degli Angeli is not so obvious.1 Overwhelmed by Luigi Vanvitelli’s encrustations of colored marble and the spectacular baroque chapels visible from the entrance, many people walk back and forth several times before realizing that they have to make a hard turn in order to find the main altar (Figure 50). Capping this enormous, confusing space is an expanse of gray, undulating Roman vaulting.

In 1549, a copy of Michelangelo’s Pietà from St. Peter’s was installed in Santo Spirito in Florence (Figure 1).1 Commissioned by the artist’s great friend and poetic collaborator, Luigi del Riccio, the work was undoubtedly meant as a celebration of Michelangelo’s achievements and the relationship between the two men.2 Public reaction to the installation of the copy, however, reveals the complexities of Michelangelo’s artistic and religious reputation in the last decades of his life.

The story behind the man suffering a particularly gruesome torment in Michelangelo’s Last Judgment fresco comes to us from the artist’s biographer Giorgio Vasari, but every tourist who enters the Sistine Chapel today has heard it.1 While Michelangelo was painting the massive fresco, one of the members of the papal court took exception to the way Michelangelo conceptualized the subject. The artist took his revenge by painting his critic with an ass’s ears, in hell, being enveloped by a massive serpent. That the serpent is also taking a rather intimate bite out of the man only adds to the comedic enjoyment of the anecdote.

Despite the continuing debate about the work, Michelangelo’s Last Judgment, like the Battle of Cascina Cartoon before it, became a site of pilgrimage for younger artists eager to draw and learn from the composition.1 Michelangelo was reported to have remarked, “Oh, how many men this work of mine wishes to destroy,” when noticing the crowd of artists copying his work in the Sistine Chapel.2 In the wake of the ongoing criticism over the fresco, the value of the artist’s influence was certainly cause for personal concern. Michelangelo might well have wondered if he was leading artists who followed his example to artistic glory but religious ruin.

Michelangelo’s poem 267 is an anomaly among his late written works. First, it is a fifty-five-line capitolo instead of a sonnet. Second, it does not explicitly take up religion or the salvation of the soul as its subject.1 Instead, we are treated to a long diatribe on the injustices of aging. Other poems from the 1550s utilize imagery of travel and pilgrimage or cry out to God for guidance and aid. Conversely, poem 267 complains about urination, heaps of shit at the artist’s doorstep, flatulence, and the artist’s various failing faculties, from the cricket that sings in his ear all night to the alarming state of his body – nothing more than “bones and strings inside my leather bag.”