Sean ‘Diddy’ Combs missed out on signing a few of rap music’s biggest acts like 50 Cent and Lil’ Kim. The late DMX was another hip hop heavyweight who made it big after Diddy turned him down. Additionally, the controversial mogul let DMX know why exactly he didn’t fit in with Bad Boy records to his face.

How DMX reacted to Diddy’s rejection

In hindsight, Diddy missed out on a massive goldmine by rejecting DMX. The Yonkers emcee released his debut album It’s Dark and Hell Is Hot to both critical and commercial acclaim back in 1998. But he quickly proved that he wasn’t a one-hit wonder by duplicating his successes …And Then There Was X and The Great Depression.

But Diddy, who helped produce similar success stories in his own right, believed that DMX lacked mainstream appeal. However, DMX didn’t hold any grudges against Diddy for his decision. Instead, Diddy’s approach to the situation actually earned some respect from the “Party Up In Here” singer.

“One thing I respect about Puff is that at least he told me to my face what he felt,” DMX said in a 2016 interview with Drink Champs (via Whos Crazy). “[Ruff Ryders executive] Dee told Puff, ‘If you like the Lox, you’re gonna love X.’  I spit, or whatever, and he was like, ‘His voice too rough and you’re not marketable.’  [I] didn’t like it, but I had to respect it.”

The late Irv Gotti, however, saw the potential in DMX that Diddy overlooked. After being hired at Def Jam records, Gotti made signing DMX to the record label his top priority. However, his associates didn’t have the same faith in the Cradle 2 the Grave star that he did, and laughed at the suggestion.

“Every meeting after that, I’m saying, ‘Yo, when can we sign DMX?’ And they not letting me do it,” Gotti said according to TV One TV. “So, I quit.”

Gotti threatening to leave his Def Jam duties was enough to convince his higher-ups to take his opinion on the New York native seriously. After returning to the label, Gotti’s Def Jam associates decided to sign DMX. Meanwhile, DMX never forgot Gotti’s unwavering support, and it solidified a deep friendship between the two.

It didn’t take long for Diddy to realize his mistake. After he heard that Def Jam was about to sign DMX, he made DMX an offer that most aspiring artists might not have refused.

“He was like, ‘I’ll lace your pockets. I’ll double what they gave you and lace your pockets,” DMX recalled.

But despite DMX’s respect for Diddy, he ultimately decided to commit to Def Jam.

Former Def Jam executives explained how DMX stopped Diddy from driving them out the business

Lyor Cohen and Kevin Liles were ultimately the two executives who Gotti had to convince to sign DMX. Cohen and Liles were running Def Jam at a time when Diddy’s Bad Boy records was at the peak of its powers. The duo admitted that they had a difficult time countering Diddy’s flashy style of music, the popularity of which was jeopardizing their business.

“Puffy was changing the conversation, going from black-and-white and shades of gray to high technicolor,” Cohen once said in an interview with Complex. “One of the critical mistakes I think they made, and I was thinking of quitting the business because I didn’t know how I fit in a technicolor world, especially with the brand Def Jam. So I remember watching The L.O.X.—now this is a real group from uptown, a real important group—the moment they started making them technicolor, I knew that I had to stay in the business and that’s when we bumped into DMX.”

The multi-platinum-selling artist showed the two music executives that their brand of hip hop was still marketable.

“They were purposely letting people know that all that aspirational stuff I’m sure has a place, all the technicolor stuff has a place, but we’re still living in a black-and-white with shades of gray world,” Cohen added. “And that’s what we represent.”