This funky R&B number was written during a trip to Los Angeles when Bailey Rae contributed some songs including "Take Your Time" and "Stay With Me (By The Sea)" to soul legend Al Green's 2008 album Lay It Down.
Bailey Rae worked with drummer Ahmir "Questlove" Thompson and keyboard player James Poyser of The Roots on this song, which she named after The Black Lily, a night that Thompson used to run on Sundays. She explained: "He'd get a chef to come to his house, and Jill Scott and Erykah Badu and the rest of The Roots would come along. All the Philadelphia scene would jam and hang out and have food. I thought, I'd love to be a part of a community like that. Am I part of a scene like that, or do I feel a bit on my own? And I just liked the image of the blackest lily."
"Crank That (Soulja Boy)" was the most successful digital track of 2007 in the US with 2,909,000 downloads. On January 6, 2008 it became the first song ever to sell 3 million digital copies in the States.
"Sloop John B" is a traditional West Indian folk song, and it was a huge hit for The Beach Boys in 1966. They tweaked the lyric, "This is the worst trip since I've been born" to "...I've ever been on" as a wink to acid culture.