Oberst told MTV News: "I think it has a sort of comedic aspect to it. The juxtaposition of the music and what's being sung about I suppose. I just think of sort of a stubborn old cowboy man that just wants to go lay in the grass and, you know, die out by the tree or something."
Conor Oberst told Mojo magazine September 2008 the story behind this song: "I have a friend who just celebrated his 75th birthday. It's a song for him: he's very strong, for the record I think he'll live forever, but we've talked about stuff like this… He doesn't want to die with his boots on, in the desert, looking up at the stars, and I think he deserves that. It's kind of a jailbreak song, a promise…if I'm ever in hospital you gotta come break me out."
"Lean On" was originally sent by Major Lazer to both Rihanna and Nicki Minaj's camps as a slower reggae track. After both parties rejected the tune, Major Lazer recruited Danish singer MØ to supply vocals and recorded it themselves.
Ariana Grande's collaboration with Zedd, "Break Free" came about after the Russian-German producer overheard Grande performing at a label showcase while he was backstage, and he mentioned to his team that he wanted to work with her.