A Close Look At Diddy and 50 Cent’s Complicated Relationship Throughout The Years

Sean “Diddy” Combs and Curtis “50 Cent” Jackson are two of the biggest names in entertainment. Both these hip-hop moguls leveraged their success in music to become powerhouses in several other spaces. This includes fashion, film, television, tech, and much more. While they’ve collaborated in the past, the men’s relationship has not always been friendly. What has been the cause of their love/hate dynamic?

Diddy was one of the first truly visible hip-hop moguls. Picking up from the blueprints of Russell Simmons, LA Reid, Barry Gordy, and more, Sean Combs helped turn Notorious B.I.G. into the greatest rapper of all time and become a star in the process as well. Following Biggie’s passing, Combs continued to increase his visibility through a successful rap career as well as helping discover and co-sign other music heavyweights like Lil Kim, Mary J Blige, Usher Raymond, Janelle Monae, French Montana, and Rick Ross.

Sean “Diddy” Combs reportedly had a chance to sign 50 Cent during his freshman era. The Queens rapper was bubbling under in New York and was touted by many to be the next great rapper to come out of the city, following Biggie and Jay-Z. 50 Cent has opened up about Diddy passing up on him, revealing he was happy because Bad Boy Records is historically a label where people “go to die.” He told The Breakfast Club, “Puffy might be the destination for anybody going nowhere. Nobody survived him. Look at it.”

Instead, 50 Cent found his co-sign in Dr. Dre and Eminem. With their blessing, he shot into the stratosphere and became a household name. 50 Cent would eventually help launch careers for Lloyd Banks, The Game, and other members of G-Unit records. Hip-hop is a genre based on rivalry, so it is understandable that 50, Diddy, and other moguls of their status have gotten competitive. While most of them stay friendly and professional, Diddy and 50 seem to go the extra mile.

In recent years things have gotten a bit more personal. 50 Cent has a son with model Daphne Joy. The pair dated for two years before separating. Joy has continued to be a hot commodity, and Diddy decided to take her on vacation recently. 50 Cent is not one to let anyone see him sweat. He took to I.G. and posted a picture of him and his son with the caption, “oh s***, that’s your mommy over there with Puffy. L.O.L. 😆😆😆 Remember what I told you the other day, these b! tche’s be crazy SMH @bransoncognac @lecheminduroi.”

Maybe 50 isn’t too upset about Diddy being with his baby momma. According to past rants from the G-Unit C.E.O., he believes Diddy is actually gay. In 2012, he accused Puff of having an affair with his manager James Cruz. “I ask puffy what he did to James Cruz to make him at like one of his girlfriends; he said what happens in Miami stays in Miami,” 50 Cent tweeted.

While visiting The Breakfast Club, 50 Cent revealed Diddy tried to take him shopping and got offended, assuming it was some type of date proposition. The rapper said he was offended by Diddy’s offer and stated, men are suppose to take women on shopping sprees. Diddy said he just thought 50 Cent needed some clothes with a laugh. 50 has also accused Puff of dating rapper Y.K. Osiris. Guess we’ll never see these two on a song ever again.

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