It is difficult to think of a music superstar who enjoyed a music-biz career at once as massive and as tortured as that enjoyed by Prince, who died Thursday at 57.

A virtual one-man industry at the height of his popularity, he became frustrated by the customary ways of the American record business over the course of his nearly 40-year run, and, after his glory years within the major label system, he pursued his art furiously and often quixotically in a succession of one-off deals and sometimes chaotic, frequently pioneering attempts to address his huge fan-base directly on his own terms.

Signed to Warner Bros. at the age of 19 in 1977, Prince issued his first album, “For You,” on the label in April of 1978. He sang and played everything on the LP. This opening salvo was not close to a hit (it peaked at No. 163), but it announced the arrival of an immense talent who said to the world, “See, I can do all this myself.” Though he quickly went on to front a band, flying solo was his natural modus operandi throughout his career.His ambition was obvious from the first, and his profile rose steadily, but relatively slowly, over the next eight years. Then, in 1984, the immediate and enormous success of his “Purple Rain” album (24 weeks at No. 1, with ultimate certification for sales of 13 million) and its accompanying smash film (a gross of $68 million and an Oscar for best original song score) gave Prince what every musician craves: leverage.

Warner Bros. rewarded him with a custom label, Paisley Park Records, and what amounted to total creative control. He released a dozen albums over the next decade (including three No. 1 titles, among them the Warner-released soundtrack companion to Tim Burton’s “Batman”), and developed the careers of auxiliary acts like the Time and Vanity 6 along the way.

The clout Prince enjoyed allowed him to operate virtually without limits, and he embraced his independence, cutting most of his work at his Paisley Park studio compound outside Minnesota’s Twin Cities. But the uncommon license he enjoyed put him on a sure collision course with his major-label partners.

By 1993, his relationship with Warner Bros. was coming to a head. He telegraphed his discontent by expunging his name from his releases, adopting the strange sex-mating symbol that would grace his albums and singles for the immediate future. He was now “the Artist Formerly Known As Prince.” He sometimes took to the stage with the word “SLAVE” scrawled in marker on his face.In a gambit seemingly designed to further ruffle Warner’s feathers, the musician issued a 1995 single, “The Most Beautiful Girl in the World,” independently via Bellmark Records. Though the move was made with the major’s approval, the writing was on the wall. His last release under contract with Warner, the fittingly titled “Chaos and Disorder,” was issued in 1996.

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From that point forward, Prince was, for all intents and purposes, an independent artist – probably the biggest that ever lived.

For the remaining 20 years of his career, he maintained control of his prolific output, employing almost every imaginable method of distribution to take his music to the public.

He never entirely turned his back on the majors. His first release following the conclusion of his Warner deal, the tartly titled “Emancipation,” was issued under his NPG (New Power Generation) imprint via a distribution deal with EMI, then still a free-standing major. His sets “Musicology” and “Planet Earth” (2007) went through Sony Music (though not without controversy); “3121” was handled by Universal Music Group.

Late in his career, he made peace with Warner Bros. – in return for ownership of his master recordings for the label – and put out two titles, “Pectrumelectrum” and “Art Official Age,” via the label in 2014.

But along the way, he employed a plethora of distribution avenues to link up with his sprawling fan base. In 2001, Prince established the NPG Music Club, a web-based, member-supported outlet for his music; more than 400,000 subscribers, paying dues ranging from a $7.70 monthly fee to a $100 premium price, ponied up for the service during its five-year run, which saw the release of several exclusive titles.

In 2007, he raised eyebrows when he issued “Planet Earth” as an exclusive freebie in the British tabloid the Mail on Sunday. Not unexpectedly, Sony declined to distribute the album in the U.K.

Prince took another stab at web-based distribution in 2009 with the establishment of the LotusFlow3r site, and issued the eponymous three-CD set digitally and physically through the platform. He appeared to be eying a similar release with his all-female backup band 3rdeyegirl in 2013 when he established a new site and offered an exclusive download of the single “Breakfast Can Wait,” but a new deal with Warner Bros. was evidently too rich to refuse.

Finally, last year, Prince announced that he would issue a new album, “HitNRun,” exclusively through Jay Z’s all-star streaming service Tidal.

Discussing the pact before reporters from the National Assn. of Black Journalists last summer, he looked back on his own career and said, “Record contracts are just like – I’m gonna say the word – slavery. I would tell any young artist – don’t sign.”

He exited the music business as he entered it: his own man, unchained and unbound.