The song is about LL searching for a girl who is streetwise. The single samples Mary Jane Girls' "All Night Long", Keni Burke's "Risin' To the Top", and The Honey Drippers' "Impeach the President", which is used as the main instrumental element of the song. It is also noted that this song is an early example of the high pitched sample rap. Around the Way Girl later appeared on LL Cool J's 1996 greatest hits album, All World: Greatest Hits.
"Around the Way Girl" peaked at #9 on the Billboard Hot 100, becoming his first top 10 single. It also was a hit on the R&B and dance music charts, where it peaked at #5 and #7 respectively. The RIAA certified "Around the Way Girl" Gold on January 15, 1991 for sales of over 500,000 copies.