As Norman Rockwell's analyst during an especially difficult period of his personal life, Erik H. Erikson encouraged Rockwell, who had been painting life “as I would like it to be,” to allow his work to flow freely out of his unhappiness. This article examines Rockwell's relationships with women—his mother and wives—and his second wife's relationships with their sons as a backdrop for a psychoanalytic interpretation, informed by Freud's theories of disavowal, joke-work, and melancholia, of Rockwell's The Art Critic. Comparison of The Art Critic with Rockwell's earlier painting, Christmas Homecoming, supports the claim for his therapeutic progress in the intervening years.