Description:Rapper Lil Wayne surpassed Elis Presley as the male with the most entries on the Billboard Hot 100. Lil Wayne has an impressive 109 songs on the charts but only 42 of the 109 songs are actually led by Weezy, while the other 67 songs features him. Elvis has 108 songs on the Billboard chart, which started in 1958. Any of Elvls' songs prior to 1958, like 'Heartbreak Hotel' aren't included on the list.(1:00)