“Gwan Big Up Urself” explores Roy Woods' sexual side. While speaking Jamaican Patois throughout most of the song—something that has become popular in Toronto’s music scene—Roy explains his desire to please his girl.

The title “Gwan Big Up Urself” is derived from Patios and Irish background. “Gwan” is Irish slang (eventually making its way into the Jamaican Patios language) for "go on.” “Big up yourself” is an expression of Jamaican heritage, meaning to give yourself praise and to enjoy what you’ve earned.

The song was released on June 4th alongside “How I Feel.”