The turn of the millennium found Dilla stressed out. Six years into a vibrant career, he had more headaches than money. Industry politics were taking their toll, from sample-clearance issues to shady record label cats proving that Tribe’s “Industry Rule number 4080” was right on the money. The second Slum Village album, Fantastic Vol. 2, was a creative triumph but generated much internal friction. While waiting for the first album to drop, Yancey’s old friends had been seeing less of him than before and Baatin had turned to hustling to pay his bills. Meanwhile Jay Dee was growing frustrated in his struggle to keep them focused on his increasingly experimental creative vision. To top it all off, every time he drove his truck down the street, Detroit police pulled him over, convinced that a young brother with fresh wardrobe had to be up to illegal activity.

He found relief by focusing on underground projects, connecting with old friends like Phat Kat—whose devastating Dedication to the Suckers EP released a whole lot of frustration. Flexing his own rhyme skills, Yancey decided to put himself forward as an artist. He signed an artist deal with MCA Records, with plans to release an album titled Pay Jay. Featuring production by the likes of Pete Rock, Kanye West, and Hi Tek, it was a strong piece of work. But internal staff changes led to the record being shelved. “You know, if I had a choice...skip the major labels and just put it out yourself, man,” Dilla vented in one interview. “Trust me. I tell everybody it's better to do it yourself and let the indies come after you instead of going their way and getting a deal and you have to wait. It ain't fun. Take it from me. Right now, I'm on MCA, but it feels like I'm an unsigned artist still. It's cool. It's a blessing, but damn I'm like, 'When's my shit gonna come out? I'm ready now, what's up?'”

With his MCA project stuck in a rut, a different album would become Dilla’s solo debut. Welcome 2 Detroit was originally slated to be a breakbeat album, but the British indie label BBE—whose name was inspired by the Universal Robot Band's 1982 track “Barely Breaking Even—told him to do whatever he wanted. Dilla responded by turning in a masterpiece, which was released under a new moniker—Jay Dee a.k.a. J Dilla. Because it featured more of his own production than Pay Jay, Welcome 2 Detroit has aged better, emerging as the superior of the two projects (and no doubt completed for a fraction of the cost). Dilla pushed the boundaries even further on his 2003 album, Ruff Draft, which contained experiments in ambient production and tracks with abstract vocals that were more like hypnotic chants than traditional raps.

After touring Europe on the strength of the album, he returned home to find his own strength failing him. What was once thought to be a case of exhaustion didn’t get better no matter how much rest he got. His parents insisted that he check into the hospital, where he was diagnosed with thrombotic thrombocytopenic purpura (TTP), a rare and very serious blood disorder. The illness may have slowed his output, but health concerns could not prevent him from making music. A longtime admirer of Madlib—the brilliant DJ, producer, and MC from Oxnard, Calif.—Dilla got word that Madlib had been recording unauthorized tracks based on Dilla beat CDs. Dilla decided to confront him—not on some cease-and-desist shit, but more to say, “If you’re going to do this, let’s make it official.” Their brilliant collaborative project, Champion Sound, marked an artistic high point in both artists’ catalogs, and further cemented Dilla’s reputation as one of the most innovative creative forces in the rap game.