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The label's first artist Kilo-G released The Sleepwalker in 1992. Over the next 4 years Cash Money played host to a number of local releases by artists such as Pimp Daddy, U.N.L.V., Ms. Tee, Mr. Ivan, Lil' Slim, B.G., among others, selling hundreds of thousands of albums without ever releasing a music video or having a Billboard hit. Cash Money's big break came in 1997 when the label's most popular artists, the Hot Boys, B.G. and Juvenile in particular, caught the attention of Universal Records executives. Juvenile's Cash Money release Solja Rags sold 200,000 copies independently. In 1998, co-CEOs Ronald "Slim" Williams and Brian "Baby" Williams signed a US$30 million pressing and distribution contract with Universal Records, entitling the label to 85% of its royalties, 50% of its publishing revenues and ownership of all masters.
Between 1998 and 2001, Cash Money churned out 18 Top Five Billboard singles and 11 platinum and multi-platinum albums, almost all of which were supervised by in-house producer Mannie Fresh. Controversy arose when two of the Hot Boys left the label claiming financial mismanagement by co-CEO Bryan "Birdman" Williams. The first artist to leave was B.G., who claimed he had never received a royalty check for any album released before 2003, an amount that would exceed 3 million dollars. The second to leave was Juvenile, who claimed he had only received half of the tour money he had accumulated over 4 years, and did not receive proper payment for his quadruple platinum album, 400 Degreez. The artist filed three simultaneous lawsuits, asking for more than $5 million in damages. The lawsuits were dismissed, however, for lack of evidence.
The departure of Cash Money's two stars did not seem to affect the performance of the Hip-Hop company. Between 2001 and 2003, the label sold 7 million albums, and the song "Still Fly" by the Big Tymers (Williams and Mannie Fresh) was nominated for two Grammy awards. In April 2003, Juvenile returned to the label for a reported $4 million deal, and in return, he signed over the rights to Juve The Great, an album which would go on to sell over a million copies.
Birdman signed deals with Lugz, Sean John, Jacob the Jeweler and Aire Watch Co. USA, among others. Former Hot Boy member Lil Wayne was named president of Cash Money Records and CEO of Young Money Entertainment, giving the rapper full creative control over all releases under the two labels.
Birdman began a conflict with fellow artist B.G. who then left the logo due to money issues. He then released the album titled "Life After Cash Money" and dissed both Birdman and Lil Wayne on other albums. B.G. then ended the feud with the group and plans on joining them for future projects.
Juvenile had a brief feud with rapper Mystikal, but they ended the conflict with a collaboration on Mystikal's Tarantula album.
Rap artist Gillie Da Kid began spreading rumors about Wayne and Birdman, specifically on his track "Frontin' Like You're Daddy," a spin off of their hit single "Stuntin' Like My Daddy." The song commented on the photos of Lil' Wayne kissing Birdman. He has also stated that their stepfather/stepson relationship never existed. The group has not been on speaking terms with Gillie since he made the allegations. Cash Money said they will sign Tukue aka Tha Beast, he also a long time friend of Lil Wayne
- Baller Blockin (2000) - A crime/action film starring Lil Wayne, Tukue ,Juvenile, B.G., Turk and Williams.
- List of Cash Money Records artists
- List of record labels
- Young Money Entertainment
- Cash Money Millionaires
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