"A Long and Sad Goodbye" is an ode to Kravitz's late father, former NBC news producer Sy Kravitz. Their tumultuous relationship was in part due to Sy's cheating on Lenny's beloved mother, Roxie Roker (star of 1970s US TV sitcom The Jeffersons). Though father and son remained at odds for much of their lives, they made their peace shortly before Sy Kravitz's death from leukemia in 2005.
Kravitz told MTV News: "My dad and I made peace with each other a few weeks before he passed, and we spent a lot of time with each other in those last days. We didn't have the greatest relationship because he had cheated on my mom and I was basically a mama's boy. It was hard-core. When your mother sits you and your father in the same room on the day he's leaving, and your mother says to your father, 'Don't you have anything to say to your son?' You'd think he'd say, 'Son, I messed up,' or whatever, some redeeming statement. But he said, 'You'll do it, too.' I didn't know what kind of weight that would carry in my life, and I realized a lot of my demons I had to battle came from moments like those. But we got over it, and that song is about that catharsis."