King Lear vowed that because he was a man he would rather go mad or die than weep. Many adult male patients in psychoanalysis have just such an internal prohibition against crying, learned individually and often culturally encouraged, a prohibition that affects their ability to process loss, maintain intimacy, and accept vulnerability. It is suggested that the appropriate psychoanalytic role with these patients is to recognize and actively address this culturally supported prohibition. In addition, it is proposed that the prohibition against men crying may be a consequence of male envy of maternal traits and other feminine characteristics. Further, it is suggested that the developmental theory that the male child must “disidentify” with the mother memorializes a phallicism that often invokes the prohibition against crying in men and is itself mistaken.