I Was Jack (You Were Diane) reminisces about falling in love to the tune years before." Owen said that he asked Mellencamp personally for permission to incorporate portions of "Jack & Diane" into the song, and recorded it after receiving Mellencamp's permission. Owen said that he wanted to record it because of the feelings of nostalgia that the lyrics evoked in him. The song is Owen's first release on Big Loud Records, following a decade on RCA Records Nashville. The song has sold 110,000 copies in the United States as of August 2018. I Was Jack (You Were Diane) "I Was Jack (You Were Diane)" is
If I Had No Loot John "Jubu" Smith played a Fender Telecaster on the song. "If I Had No Loot" incorporates a New jack swing beat, pronounced guitar licks, and a tempo of 108 beats per minute. It has 1960s Stax southern soul influences. The song also contains vocal samples from hip hop songs, including the "da-da-da-day" chant from Boogie Down Productions' 1987 song "Remix for P Is Free" and the line "and you can "new jack swing" on my nuts!" from Ice Cube's 1991 song "The Wrong Nigga to Fuck Wit". According to Raphael Wiggins, the song is about "fair-weather friends" and "people who