As the world mourns Prince, the industry also bids farewell to Prince, Inc.

Prince Rogers Nelson’s moves within the music business were often as prophetic and mysterious as his art and public persona. Much the way he could write, sing, produce, and play all of the instruments on his songs, his career was marked by a similar insistence on mastery over how that music was sold and distributed. In the mid-1980s, after the multimedia success of Purple Rain, he convinced Warner Bros. to help launch the Paisley Park Records label from his Minnesota estate. By the '90s, he was appearing in public with the word "slave" on his cheek, changing his name to an unpronounceable glyph, and releasing a triple album via his post-Paisley Park imprint, NPG. As a young music fan at the time, I remember hearing about the industry travails of "the Artist Formerly Known as Prince" as much as I heard his recorded output.

That iconoclasm alone would provide a meaningful legacy. Speaking with the New York Times, producer and longtime Prince associate Jimmy Jam drew a link between Prince's experiments with complete artistic control and such present-day releases as Kanye West's ever-evolving The Life of Pablo.

More than a business-minded person savvy enough to want ownership of his music, though, Prince—like David Bowie—was also a pioneer when it came to the emerging online world. There was a CD-ROM. There was a monthly online subscription service, NPG Music Club; a successor was called Lotusflow3r, which perhaps not coincidentally resembles the song title "Lotus Flower" by Radiohead, who followed Prince's direct-to-fans approach with 2007's "pay what you like" In Rainbows. Prince "was sex," according to the The Guardian. He "was technology," according to the Times. And his later falling out with the online realm, similarly, was business.

The Purple One's fights with bootleggers and streaming services went beyond the norm, but he consistently defended them using the cold logic of the bottom line. And he repeatedly engaged in sly winks—such as titling a song after a popular Prince meme or using Dave Chappelle's impersonation of him as single artwork—that showed he was very aware of the internet meta-realm he was ostensibly rejecting. Prince wanted be free to create his music but he didn't necessarily want it to be free to consume.

"He was an independent voice," Pandora CEO Tim Westergren told me Friday, recalling a discussion he once had with Prince. "He was always just looking out for artists, trying to help them get a fair share of what was going on in digital. He was a musician's musician, trying to figure it out with everyone else."

Here's a timeline of Prince's singular dance with the music business, with a particular emphasis on the digital realm. In his interactions with interactivity, as in so many other aspects of Prince's work, you'll find few black-or-white conclusions, but plenty of purple.

1977: Just after turning 18, Prince signs a six-figure deal with Warner Bros. The contract states Prince will produce his own albums, starting the young musician down a career with an unusual degree of artistic control. He benefits, too, from a music industry in its disco-era heyday: His debut album, 1978's For You, peaks at No. 163 on the U.S. Billboard 200 chart. But the label, flush enough to be patient with its talent, stands by him while 1979's Prince, 1980's Dirty Mind, and 1981's Controversy never crack the Top 20.