Diddy Thought Lil' Kim Was 'Too Pretty' to Be a Rapper

Sean “Diddy” Combs and Lil’ Kim are two icons of hip-hop with decades of experience to their names. The two rappers have a complicated history together and have been at each other’s sides for much of their careers.

Diddy and Lil’ Kim’s friendship dates back to the ’90s

Diddy and Lil’ Kim’s relationship can be traced back to another legendary rapper: The Notorious B.I.G. Diddy signed Biggie to his new record label Bad Boy Records in 1993 and helped launch the Brooklyn-bred MC to stardom.

Before his big break, Biggie often participated in rap battles on the streets of Brooklyn. One day, as a teenager, Biggie met Lil’ Kim after hearing her rap on the corner of Fulton Street in their home neighborhood of Bedford-Stuyvesant. He asked her to join his group, Junior M.A.F.I.A., and they began recording music together. 

“He became my friend, my lover, my everything. I was his biggest fan.” Kim told Entertainment Weekly in 2016. “He knew I would be the biggest female rapper. I think I inspired him to want to do different things and be different.”

Naturally, it wasn’t long before Biggie introduced the two.

Diddy thought Lil’ Kim was ‘too pretty’ to be a rapper

In a 2011 interview with Sway Calloway on MTV News, Kim looked back on when she first met Diddy — known back then as Puffy or Puff Daddy — and his regard for her talents as a rapper.

“Biggie did bring me to Puffy,” she recalled. “He said, ‘She’s too pretty to be rapping. Female rappers don’t look like her. What am I supposed to do with her?’”

Lil’ Kim and Diddy’s beef

Diddy was so unimpressed with Kim as a rapper that he never signed her to Bad Boy Records, even after her debut album Hard Core went Platinum.

Kim told MTV in 2011 that she and Diddy were no longer on speaking terms. She was hurt after up-and-coming rapper Nicki Minaj took a shot at her on Diddy’s song with Dirty Money, “Hello Good Morning.”

Kim also mentioned that Diddy never visited her when she was incarcerated between 2005 and 2006 on federal perjury charges. “I’m bothered by his actions, because I rolled with Puffy to the bitter end, and still would have rolled with him,” she said. “Puffy never came to see me in prison, not one time. He didn’t write me a letter. He didn’t say, ‘Here’s a number for Kim to call,’ not one time.”

Diddy and Lil’ Kim’s relationship today

Diddy and Lil’ Kim have since buried the hatchet, and continue to work together to preserve Biggie’s legacy. In 2016, the two stars embarked on the Bad Boy Family Reunion Tour across the United States, which brought together some of the Diddy’s biggest collaborators from the past, including DMX, Faith Evans, and The LOX.

“This isn’t just a concert — this is a moment in hip-hop and R&B history,” he said in a statement. “The family and I are so excited to welcome fans into this once-in-a-lifetime experience. This tour is 20 years in the making, and is a celebration of the hits and the Bad Boy lifestyle. The Bad Boy Family has set the standard for concert excellence, and this tour will be a testament to that!”

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