Jay-Z’s $1 Million ‘Big Pimpin’ Request Faces Initial Resistance from Pimp C, Claims Label Executive

In a surprising turn of events, music executive Greg Taylor recently revealed an interesting behind-the-scenes story about Jay-Z and UGK’s collaboration on the hit track “Big Pimpin” in 2000.

Despite the success of the song, Pimp C initially hesitated to join the project, leading to a $1 million deal that took an unexpected turn.

During an interview with The Art Of Dialogue, Taylor shared the details of a phone call with Dame Dash, “I called Pimp on the phone like, ‘Yo Pimp’… I got a million-dollar check for you and all we wanted was a $100,000. He was like, ‘Who’s that with?’ I said, Roc-A-Fella. He was like, ‘Ain’t that over there with JAY-Z.’ I was like, ‘Yeah.’ He was like, ‘Man, tell him to take that check and give it to 2Pac momma. He gonna be stealing all my sh*t.”

However, the situation took an unexpected turn when Jay-Z overheard Pimp C’s comments during the phone call. Taylor admitted to quickly realizing Jay-Z was in the room and had heard the playful diss. Swiftly, Taylor apologized to Jay-Z, highlighting the need to clean up the misunderstanding.

Despite this initial hiccup, “Big Pimpin” moved forward after Jay-Z and Pimp C sat down for a dinner meeting with Pimp C’s mother, clearing up any lingering misunderstandings. However, the journey towards collaboration wasn’t without its challenges.

Roc-A-Fella A&R Kyambo “Hip-Hop” Joshua recalled a moment during the collaboration where Pimp C misinterpreted one of Jay-Z’s bars. Pimp C initially thought Jay was saying that he was playing with his d*ck in the truck,” Joshua recounted in a podcast interview last year. “So he’s like, ‘Man, I’m not getting on no song with another man talkin’ bout playing with his self in the truck!”

Joshua clarified that the misunderstood line was actually meant for female passengers, not male-related content as Pimp C had initially believed. With this clarification, Pimp C grew more comfortable, and the collaboration continued.