David Bowie’s musical legacy is unquantifiable and profound, but his most daring financial experiment had fewer ripple effects. The “celebrity bond” industry remains a somewhat exotic option nearly two decades after the creation of “Bowie Bonds.”

In 1997, Bowie, born David Robert Jones, securitized revenue from 25 albums (287 songs) released before 1990. At the same time, he swapped distribution rights on his back catalogue for a $30 million advance on future royalties in a deal with EMI. The 10-year “Bowie Bond” he created with banker David Pullman promised a 7.9% return and raised $55 million, along with a media frenzy. A flurry of other artists followed, but the Bowie Bonds skidded toward junk status by 2004, downgraded by Moody’s from A3 to Baa3.

The Bowie Bonds were purchased by Prudential Insurance Company of America in 1997, and Prudential sold off the Bowie Bonds with its 2003 sale of Prudential Securities to Wachovia Securities, which in turn was merged with Wells Fargo on Dec 31, 2008. A company spokesperson for Wells Fargo couldn’t immediately confirm what happened to the asset after that.

“I think these celebrity bonds totally lost favor,” said Barry Bergman, president of the U.S. chapter of the Music Managers Forum, an organization that advocates for artists’ and managers’ business interests. “I haven’t heard much about any of these things in years. I heard from people in the industry that these deals were not what they appeared to be. They seemed to have all kinds of things attached to them, provisions to take care of the recoupment, that ultimately hurt the acts.”

Other novel approaches to monetizing music have also come to be eyed cautiously. Parviz Omidvar of Royalty Advance Funding makes loans based on artists’ catalogues and criticizes bonds are too rigid for the unpredictable revenue streams of music. “Music is an intangible asset, so there’s no good recording system like there is in real estate to know who has what claim to the collateral,” he said. But Omidvar conceded that complexity means “I wouldn’t say our loans are straightforward and traditional, because 99.99% of lenders wouldn’t touch the loans we make."

There are other benefits in terms of flexibility, and Royalty Advance Funding does its due-diligence by talking to the music industry players to look at the income stream and see what they're trying to accomplish before structuring around their needs. Of course, that hasn’t stopped some artists from suing, but he’s dismissed those suits in media as “buyer’s remorse.”

Anyone introducing a new financial service in the music industry will encounter tripwires of distrust. The music industry has long been notorious for profiting financiers far more greatly than artists; African American pioneers of rock and jazz in particular often died in poverty or after litigation over exploitative contracts. But in the Bowie case, celebrity bonds don’t seem to have failed the artist as much as investors. The financial product might have been swiftly overtaken by technology. The ink had barely dried before online music sharing rose to threaten recording revenue.

Pullman told TheStreet that he remains bullish on celebrity bonds. “The Bowie Bonds never missed a payment,” said David Pullman. He declined to comment on the current status of the bonds, comparing it to revealing details about a person’s mortgage. He admits that introduction of this new form of securitization was “a roller coaster.”

“This is the most complex area in the business I’ve ever seen,” Pullman said. He’s been repeatedly in court suing Prudential Insurance, Royal Advance, and former partners over the years with financial and intellectual property claims.

Lessons learned, according to Pullman. “This is not cookie cutter process," he said. "Doing one doesn’t make the next easier. They take six months to a year to do, and then people will attempt to copycat.”

He now views artist catalogues “like redwood trees,” he said, given how long they take to grow and are irreplaceable. But the maturing of online music sales has restored his faith in the mechanism. While Youtube and other platforms for consuming music don’t carry fees, they aren’t free. Artists, representatives, and publishers can factor in payments from subscription radio, advertiser-supported streaming services, and other outlets, and likely losses from piracy, before issuing bonds, he said. “Everything you hear, someone paid for that,” he said “It’s just a matter of tapping into that.” Artists can also narrowly specify a revenue stream, like radio broadcast, to securitize, he said.

“Music interest has never waned; it’s only increased,” Pullman said. “What changed is that people got nervous.”