Okrent shines new light on Sondheim’s complicated emotional life, wavering self-confidence, and alcoholism, drawing on the artist’s intimate correspondence with such notable figures as Hal Prince, Leonard Bernstein, and Arthur Laurents; exclusive interviews with his close friends and collaborators, including James Lapine and John Weidman; and Sondheim’s own oral history, which remained closed until his death. He also reveals a previously unknown (and crucial) aspect of the infamous letter from Sondheim’s mother that made him believe she regretted his birth. As Okrent explores the ways Sondheim’s music and lyrics express the inner man, he shows us a life that was defined by two parallel arcs: the movement from alienation to connection, and from ambivalence to resolution.