Duritz has cited in interviews that the angst he felt not being around his grandmother for a long time due to frequent touring, up until her death while he was in Perth, Australia, inspired this song:[1]
In the last five years of her life I barely saw her because I was always working. She didn't recognize me. To her I was this fat, hairy, bearded guy with dreadlocks. I think I scared her some of the time. And then it was too late......It's about losing that girl. It's a snapshot about when I am very much in love but I know I have to leave ... I wasn't good at being caring. It was a lot to handle me. I was 10,000 miles away and I wasn't there for her.
Duritz explained in an April 2008 interview the broader meaning of the song:[2]
‘Hanging Tree’ is about looking in a very banal way. Sitting in a cafeteria with someone and losing your connection with someone in a very angry way in the most banal conversations in a cafeteria.
As with the tracks "Sundays" and "Insignificant", imagery pertaining to the Greek myth of Icarus appears in the song, specifically in the lyric: "I got a pair of wings for my birthday and I'll fall down through the sun this evening."
Duritz reportedly preferred having either this song or "When I Dream of Michelangelo" released as the lead single, as he believed either one of those tracks better represented the album as a whole thematically, in contrast to "You Can't Count on Me".