<b>Ray Charles</b> was not only a talented music star for more than three decades, but a shrewd businessman as well. In the early '60s, he was one of the first Black music artists to gain ownership of his own master recordings in brokering his deal with ABC-Paramount. Having written nearly 200 songs, Charles also operated his own publishing companies, Tangerine Music and Racer Music. <i>—Janell Hazelwood (Additional reporting by Kahliah Laney)</i>
In August 1991, <b>Prince</b> inked a $100 million deal with Warner Bros., making him the highest-paid artist at the time. The deal included two joint record companies as well as a vice president post for him. In 1993, the pop and rock icon would become "the Artist Formerly Known as Prince" during a <a title="legal battle with the label" href="http://www.billboard.com/news/prince-to-hold-off-on-recording-until-piracy-1005250772.story#/news/prince-to-hold-off-on-recording-until-piracy-1005250772.story" target="_blank"><strong>legal battle with the label</strong></a> over artistic and financial control of his music. After a long, highly publicized battle, in which he began performing in protest using only a symbol as his name, he was able to gain release from the contract, serving as one of the most prolific public examples of an artist's success in standing up for his artistic beliefs and financial due.
<b>Master P</b> was the first rapper to gain 100% ownership of his masters in the '90s, a feat that was not common in the entertainment industry. Many labels retained much of the publishing rights of their artists, so P striking a deal for full ownership was a groundbreaking milestone. The Southern hip-hop pioneer, who was also the <a title="first hip-hop artist to make $100 million" href="http://www.xxlmag.com/features/2007/08/master-p-1998-man-of-the-year/" target="_blank"><strong>first hip-hop artist to make $100 million</strong></a>, founded his own label, No Limit Records, in 1990, with a platinum-selling roster of talent, and was also the first Black rapper to own a cable TV channel, <strong><a title="Better Black TV" href="http://betterblacktv.com/" target="_blank">Better Black TV<strong></strong></a>, 2009.
<b>Berry Gordy</b>, founder of Motown Records, sold 50% of Jobete Music Co., the publishing arm of the label, to EMI Music Publishing for $132 million in July 1997, in what was considered one of the most significant music publishing deals of all time. Motown churned out more than 100 No. 1 hits in more than three decades, and changed the face of soul music with its top-selling roster.
<b>Jay-Z</b> inked a $150 million deal with Live Nation in April 2008, making a groundbreaking move in the music industry with a <a title="360 model that benefits both the artist and the music tour giant" href="http://www.blackenterprise.com/2011/06/13/behind-the-music-jeff-robinson-on-the-360-deal/" target="_blank"><strong>360 model that benefits both the artist and the music tour giant</strong></a>. The hip-hop entrepreneur left his longtime label Def Jam for a deal that includes financing for his own entertainment venture, as well as recordings and tours for the next decade.
Hip-hop powerhouse <b>Curtis "50 Cent" Jackson</b> worked with Glacéau to create his own VitaminWater drink, Formula 50, in 2004, and got a stake in the company. After Coca-Cola's $4.1 billion purchase of Glacéau in 2007, Jackson <a title="earned an estimated $100 million" href="http://www.forbes.com/2011/03/09/billionaires-11-focus-sean-combs-jay-z-dr-dre-be-billionaire_slide_6.html" target="_blank"><strong>earned an estimated $100 million</strong></a>, a major move for a hip-hop artist at the time.