A top 20 hit in 2009, “Break Up” was r&b singer Mario’s first hit in five years. It was also the first hit single to feature young up-and-coming rapper Gucci Mane, who would not come close to this level of pop success until his appearance on Rae Sremmurd’s “Black Beatles” in 2016. In it, the two (along with newcomer Sean Garrett) deal with a breakup with either resignation or macho come-ons for the woman to stay.