“Big Pimpin'” was the fifth and final single from Jay-Z’s fourth studio album Vol. 3… Life and Times of S. Carter. The track is an ode to the “pimping” lifestyle, that is, sex with girls without becoming emotionally attached to them.

Produced by Timbaland, it is notable as one of the first songs where Southern rap truly broke into the mainstream with the appearance of Texas natives Bun B and Pimp C, known together as the Underground Kingz (UGK).

The track is one of Jay-Z’s most successful singles, peaking at #18 on the Billboard ‘Hot 100’ and spending twenty weeks on the chart. It ranked at #467 on Rolling Stone’s list of “The 500 Greatest Songs of All Time”. In 2004 the track had a chart resurgence when it featured on Jay and Linkin Park’s Collision Course mash-up album.

Despite the song’s huge commercial success, Hov nowadays seems to be embarrassed by the song. In his memoir, Decoded, he disavowed “Big Pimpin'” and its lyrical content:

Some [lyrics] become really profound when you see them in writing. Not ‘Big Pimpin’.‘ It was like, 'I can’t believe I said that. And kept saying it. What kind of animal would say this sort of thing?’