Questlove traces sampling from Wild West years to AI on Billboard's On the Record

Questlove says hip-hop sampling ran as an unpoliced “Wild West” from 1988 to 1991, and new tools could change it again.

The musician, producer and director made the comments on Billboard’s On the Record, in a conversation about the history of sampling and newer trends including microchopping, catalogue sales and generative AI. Billboard

Sampling, the reuse of a slice of an existing recording inside a new track, shaped early hip-hop. Questlove put its freest period at 1988 to 1991. Nothing was policed. Producers lifted drums, voices and breaks without a clearance system to stop them.

That changed after copyright infringement litigation involving rapper Biz Markie. The case brought new rules around clearing samples, which added paperwork and cost. For many producers, that created logistical and financial barriers to a technique that had been wide open.

Clearance often means identifying everyone who owns a piece of the original recording and negotiating a fee or a share of the new song. For independent producers, the cost and delay can decide whether a track gets finished or released. That practical weight explains why the Biz Markie case is still cited more than three decades later.

Microchopping, the practice of cutting a sample into very small fragments and rearranging them, is one of the responses Questlove discussed. He also pointed to catalogue sales, in which artists sell the rights to their older recordings, and generative AI, software that can create new audio from prompts and existing material. Each raises fresh questions about permission, payment and credit.

Those questions reach beyond the studio. Catalogue deals affect who controls older music and for how long. AI tools raise questions about whose work trains a system and how those players are paid. Producers now weigh creative choice against legal risk in a way the late 1980s did not require.

Questlove said sampling works because of the idea of a community creating something together. The Roots, the band he co-leads, know both sides of that exchange. Their own recordings have been sampled by artists including Drake, Kendrick Lamar, Wale and Logic.

The conversation was not only about technique. Questlove also discussed the evolution of hip-hop and Earth, Wind & Fire on Billboard’s On the Record. Billboard

He directed a documentary about the group, released on HBO Max. The film premiered on 7 June on HBO, according to an earlier Billboard interview, and chronicles the band’s development, its highs and lows, its spiritual meaning and its lasting legacy. Billboard

What makes this stand out is the scale of his listening. Questlove has spoken about holding a collection of 200,000 records. Within that archive, he singled out Earth, Wind & Fire’s All ’n All for its immersive experience and said it has earned a permanent spot in his collection.

For newcomers, that detail lands the wider point. Sampling lives in studio craft and in record-collecting, memory and reuse, carried from one generation of listeners to the next.