Leo Steinberg was one of the most original art historians of the twentieth century, known for taking interpretive risks that challenged the profession by overturning reigning orthodoxies. In essays and lectures that ranged from old masters to contemporary art, he combined scholarly erudition with an eloquent prose that illuminated his subject and a credo that privileged the visual evidence of the image over the literature written about it. His writings, sometimes provocative and controversial, remain vital reading. For half a century, Steinberg delved into Michelangelo’s work, revealing the symbolic structures underlying the artist’s highly charged idiom. This volume of essays and unpublished lectures elucidates many of Michelangelo’s paintings, from frescoes in the Sistine Chapel to the Conversion of St. Paul and the Crucifixion of St. Peter, the artist’s lesser-known works in the Vatican’s Pauline Chapel; also included is a study of the relationship of the Doni Madonna to Leonardo. Steinberg’s perceptions evolved from long, hard looking. Almost everything he wrote included passages of old-fashioned formal analysis, but always put into the service of interpretation. He understood that Michelangelo’s rendering of figures, as well as their gestures and interrelations, conveys an emblematic significance masquerading under the guise of naturalism. Michelangelo pushed Renaissance naturalism into the furthest reaches of metaphor, using the language of the body to express fundamental Christian tenets once expressible only by poets and preachers. Michelangelo’s Paintings is the second volume in a series that presents Steinberg’s writings, selected and edited by his longtime associate Sheila Schwartz.