Jay-Z rose to fame in the late 1990s in the wake of iconic New York rappers such as Nas and The Notorious B.I.G. At the turn of the millennium, Jay-Z released the single “Big Pimpin’” with Pimp C and Bun B of UGK. And though the two hip-hop icons eventually jumped on the track with Jay, Pimp C needed some convincing after deducing that one of Jay-Z’s lyrics in the song was about masturbation.
Jay-Z recorded ‘Big Pimpin” with Pimp C and Bun B of UGK
Texas natives Pimp C and Bun B formed the Underground Kingz — a.k.a. UGK — in the late 1980s. They released albums throughout the 1990s and 2000s and were instrumental in showing that Southern rappers were not to be taken lightly.
In late December 1999, Jay-Z released his fourth studio album Vol. 3… Life and Times of S. Carter. The following spring, Jay-Z released the UGK collab “Big Pimpin’” as a single. The song was the most successful single from the album, peaking at No. 18 on the Billboard Hot 100 chart and driving Vol. 3… Life and Times of S. Carter to triple-platinum status. It would be UGK’s highest-charting single, both as lead and featured artists, and the only song of theirs to crack the top 20 on the Hot 100.
Pimp C thought Jay-Z was rapping about masturbating
In a January 2023 appearance on the R.O.A.D. Podcast, famed Roc-a-Fella A&R Kyambo “Hip-Hop” Joshua reflected on how “Big Pimpin’” first came about in the late 1990s and how Jay-Z and company had to work hard to convince Pimp C to join in on the track. First, Pimp C had to be convinced to do the song with Jay-Z in the aftermath of the death of his friend Tupac Shakur, who had expressed his disdain for the Brooklyn-bred rapper. Pimp C refused to do the song, and after agreeing to do it, he had to be convinced again after he heard one lyric in particular.
“He thought Jay was saying that he was playing with his d*** in the truck,” Joshua recounted. “So he’s like, ‘Man, I’m not getting on no song with another man talkin’ bout playing with hisself in the truck! Young Hop, you my boy, but what you tryna have me doin’, man?’ He said, ‘That’s like career suicide!’”
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The line in question — “Let ’em play with the d*** in the truck” — actually referred to women who would join Jay-Z in the car. “[Pimp C] said, ‘I could see that. That makes sense now.’ Then he kinda got closer to doing it,” Joshua remembered.
“He really was well aware of what he was doing,” Joshua praised the late Pimp C. “He really broke down his whole flow and his whole thing. Like, ‘I rap with the vocal tone of Run[-D.M.C.], with the choppiness of Scarface, and the Southern drawl of Willie D.’ And he did it for me, like in my face.”
Jay-Z looks back on ‘Big Pimpin” with regret
Even though “Big Pimpin’” remains beloved by fans today, Jay-Z doesn’t necessarily look back on the song with pride. In a 2010 interview with The Wall Street Journal, he admitted that “Big Pimpin’” is one of his songs that hasn’t aged well for his liking.
“Some [lyrics] become really profound when you see them in writing. Not ‘Big Pimpin’. That’s the exception,” he said. “It was like, ‘I can’t believe I said that. And kept saying it. What kind of animal would say this sort of thing?’ Reading it is really harsh.”
