Claim: Lil Wayne has made at least six songs.

Dwayne Michael Carter Jr. -LRB- born September 27 , 1982 -RRB- , known professionally as Lil Wayne , is an American hip hop recording artist . In 1991 , at the age of nine , Lil Wayne joined Cash Money Records as the youngest member of the label , and half of the duo The B.G. ` z , alongside fellow New Orleans-based rapper Lil ' Doogie . In 1996 , Lil Wayne joined the southern hip hop group Hot Boys , with his Cash Money label-mates Juvenile , Young Turk and Lil ' Doogie -LRB- who now goes by B.G. -RRB- . Hot Boys debuted with Get It How U Live ! , that same year . Most of the group 's success came with their platinum-selling album Guerrilla Warfare -LRB- 1999 -RRB- and the 1999 single `` Bling Bling '' . Along with being the flagship artist of Cash Money Records , Lil Wayne is also the Chief Executive Officer -LRB- CEO -RRB- of his own label imprint , Young Money Entertainment , which he founded in 2005 .   Lil Wayne 's solo debut album Tha Block Is Hot -LRB- 1999 -RRB- , was certified platinum by the Recording Industry Association of America -LRB- RIAA -RRB- . His subsequent albums , Lights Out -LRB- 2000 -RRB- and 500 Degreez -LRB- 2002 -RRB- , went on to be certified gold . Wayne reached higher popularity with his fourth album Tha Carter -LRB- 2004 -RRB- , which was led by the single `` Go D.J. '' and his appearance on Destiny 's Child 's Top 10 single `` Soldier '' , that same year . The album was followed by Tha Carter II -LRB- 2005 -RRB- , as well as several mixtapes and collaborations throughout 2006 and 2007 . Wayne gained more prominence with his sixth album Tha Carter III -LRB- 2008 -RRB- , which became his most successful album to date , with first-week sales of over one million copies in the United States . The album won the Grammy Award for Best Rap Album and includes the hit singles `` Lollipop '' , `` A Milli '' and `` Got Money '' .   Following the success of Tha Carter III , Wayne decided to record a rock-esque album titled Rebirth . The album , released in 2010 , was certified gold by the RIAA , despite a generally negative critical response . In March 2010 , Lil Wayne began serving an 8-month jail sentence in New York after being convicted of criminal possession of a weapon stemming from an incident in July 2007 . Wayne 's eighth album I Am Not a Human Being -LRB- 2010 -RRB- , was released during his incarceration . His 2011 album and first following his release , Tha Carter IV , sold 964,000 copies in its first week of availability in the United States . It includes the singles `` 6 Foot 7 Foot '' , `` How to Love '' and `` She Will '' . On September 27 , 2012 , Lil Wayne passed Elvis Presley as the male with the most entries on the Billboard Hot 100 chart , with 109 songs . The record has since been passed by other artists . Lil Wayne 's thirteenth studio album , Tha Carter V , has been delayed multiple times and has no scheduled release date . Lil Wayne has sold over 100 million records worldwide , including sold more than 15 million albums and 37 million digital tracks in United States , making him one of the best-selling artists of all time .