"Big Pimpin'" is one of Jay-Z's most well-known hits, and was a high-profile moment for UGK, who deliver a scene-stealing performance on the Timbaland-produced smash. But the late Pimp C was famously reluctant to perform on the song initially, and in a recent conversation with The Steven Sulley Study podcast, Bun B revisited the making of the song and shared that C's apprehension had a lot to do with his respect of Tupac Shakur.
“So, 2Pac was not a Jay-Z fan, this is very well-known,” Bun B says. “2Pac was not a Jay-Z fan in his career, and when there was a West Coast, East Coast beef, he felt Jay-Z was part of the collective that were his enemies. Jay-Z was good [friends] with Biggie, good friends with Biggie, who 2Pac felt betrayed him when he got shot."
“Jay-Z had been introduced to UGK by a big DJ in New York named Clark Kent. And he’s like, ‘I like these guys, I wanna work with them,'” Bun continued. “And Pimp C did not want to fuck with people that 2Pac did not fuck with, because he thought 2Pac was the best judge of character.”
2Pac loomed large, and in 1999, a lot of the wounds from the bitter feuding that had defined the mid-1990s were still fresh. For Pimp C, these were all major factors in whether or not he'd collaborate with Jay.
“When that first call came from Jay-Z, we were at the house in Atlanta, and [Pimp C] looked up at the wall. And he just stared at the picture. And I’m like, ‘What are you doing?’ And he said, ‘I’m thinking what would 2Pac do right now? And 2Pac wouldn’t want me to fuck with him. That’s why I said, I’m not coming to New York.”
Jay's mainstream appeal has also been cited as a reason for Pimp C's reluctance to appear on "Big Pimpin'," but thankfully, UGK and Jay-Z did team up for the song. "...Pimpin'" wound up becoming a Top 20 hit for the artists, and it remains the highest charting single in UGK's discography.