The Angel Pietà or Pietà with Angels was a common iconographical type in Renaissance Italy. However, much of its tradition and meaning still have not been adequately investigated. This paper serves to describe the history and iconography of the Angel Pietà and present three new interpretations of the enigmatic Angel Pietàs of three artists: Andrea del Sarto, Rosso Fiorentino, and Jacopo da Pontormo. The paper elucidates a Virgin as Priest motif in Andrea's painting, a relationship to the Holy Week rite of the Tenebrae in Rosso's painting, and a connection to relief and an emphasis on the viewer in Pontormo's painting.