Lil Wayne first entered the Billboard Hot 100 as a featured artist on the hit Juvenile song, “Back That Azz Up,” in 1999. His first single “The Block Is Hot,” the title track to his debut album, was also on the Billboard Hot 100 that same year. He continued to have hits on the Billboard Hot 100 with songs like “Go DJ” (2004), “Lollipop” (2008) and “She Will” (2011). He hit the charts as a featured artist with songs like Destiny’s Child “Soldier” (2004), Jay-Z and T.I.’s “Swagga Like Us” (2008) and Drake’s “Forever” (2009).
Since breaking the record, Lil Wayne has continued to have singles on the Billboard Hot 100, such as “Love Me,” off his recent album I’m Not a Human Being II, Big Sean’s “Beware” and his newest addition, 2 Chainz’s “I Do It.” -Ariana LaBarrie
