Hip-hop artists continue to break records when it comes to business dealings. Although it’s no longer a rare occurrence to see a rapper land a multi-million dollar endorsement deal, it’s still fascinating to see how well these brandmakers have infiltrated the mainstream and have become the go-to sources to help hawk and sell products.  Not to mention, rappers have become an inspiration for African-American entrepreneurship, having become owners of their music and business offshoots like fashion labels. Here’s a list of some of the biggest deals that have helped to enrich the bank accounts of the biggest names in the rap game.

50 Cent

Curtis “50 Cent” Jackson boldly thanked Vitamin Water during a televised performance a few years ago. That’s probably because his deal with the company turned into one of the biggest in hip hop history. In May 2007, Coca-Cola  bought Vitamin Water for $4.1 billion. Timing is everything, as 50 cent had recently bought into the bottled water company. After the sale,  business experts estimated his take from that sale, after taxes, was about $100 million.

Shawn “Jay Z” Carter

Shawn “Jay Z” Carter once said, “I’m not a businessman, I’m a business, man.” Obviously, he’s got a head for it. In 2007, the originator of  Roc-a-wear sold his clothing label to Iconix for $204 million.  Jay-Z, also started his own label, Roc Nation, in partnership with Live Nation. It was an unprecedented “360” deal reported at $150 million.

Sean “Diddy” Combs

Sean “Diddy” Combs is one of the most astute businessmen in business period.  One of his most recent business deals with Ciroc vodka is reason enough. Diddy signed a multi-year deal to develop the Ciroc vodka brand, which is one of Diageo PLC’s premium lines. The deal gives Diddy 50 percent of the profits which could be worth over $100 million depending on the success of the branding campaign.

Russell Simmons

Rusell Simmons may well be considered the God-father of hip hop businessmen. In 2004. he sold  his clothing line Phat Farm for nearly $140 million to Kellwood Company. That deal came just five years after he handed over the reigns on Def Jam allowing Universal Music Group to buy him out for a cool $100 million.

Aliuane “Akon” Thiam

Hip Hop artist Akon’s global deal with Pepsi surrounding the World Cup, arguably the biggest sporting event on earth, helped him land on Forbes short list of Hip hop Cash kings behind only Diddy and Jay Z. The international superstar raked in $21 million last year alone. His business savvy has propelled his interest in not only other companies but also his own with Konvict Music, and Konvict clothing.