Gotfryd, Bernard, photographer · Public domain

Sondheim wrote lyrics for West Side Story and Gypsy while still in his twenties, mentored by Oscar Hammerstein II, before becoming the composer who pushed the American musical toward darker, more ambivalent material than the genre had attempted. Company, Sweeney Todd, Into the Woods, and Sunday in the Park with George — the last of which won the Pulitzer Prize for Drama, one of the few musicals ever to — reshaped what a Broadway show could be about. He won eight Tony Awards, eight Grammys, and the Presidential Medal of Freedom.