A revelatory look at the complex inner world of one of the twentieth century’s most beloved theatrical composers Stephen Sondheim (1930–2021) was a towering figure in American musical theater. Celebrated for such iconic Broadway shows as Company, Sweeney Todd, and Into the Woods, his accolades include eight Tony Awards, multiple Grammy Awards, an Academy Award, and a Pulitzer Prize. In this intimate biography, Daniel Okrent follows Sondheim through the tumult of his upbringing and his parents’ divorce, his life-changing relationship with Oscar Hammerstein II and subsequent immersion in musical theater, and his rise to fame as both a lyricist and composer. 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.