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If reports are to be believed, Michael Jackson may have as many as 100 unreleased songs that he left behind. Though it may be quite some time before any songs ever get out, it’s certain that fans will be clamoring for songs they’ve never heard.

But if pop history has taught us anything, it’s that posthumous music releases can be a bit of a nightmare both for the people in control of the estate and the fans craving new music. In fact, sometimes that music actually hurts the legacy of the artist.

When Jimi Hendrix died in 1970, he left behind at least one incomplete album and many more unfinished tracks, demos and outtakes. But for decades, the previously unreleased songs were released haphazardly and were underproduced. It wasn’t until Hendrix’s sister managed to gain control of his catalog that the recordings were considered reasonable enough for commercial release. Hendrix albums have slowed and there are still legal battles over Hendrix’s legacy, but the reconstructed First Rays of the New Rising Sun and the restored Live at Monterey are both keepers. But be warned: A lot of the post-1970 Hendrix releases are horrible.

The same could be said of Tupac, but in reverse. When the rapper was killed in 1996, he left behind dozens of hours of verses, freestyles, outtakes and completed songs. In his case, the albums released closest to his death — The Don Killuminati: The 7 Day Theory (released as Makaveli) and R U Still Down? (Remember Me) — are both excellent, mostly because they were fully realized (or close to it) at the time of his death. After that, things sort of go downhill. There are moments of brilliance on Still I Rise and Better Dayz, but it’s been largely diminishing returns since the end of the century.

Tupac rival the Notorious B.I.G. has had an even rougher time of it. Biggie Smalls was killed in 1997 just before the release of his recently completed Life After Death. Biggie didn’t leave behind very much in the way of unreleased recordings — basically, most everything he recorded he ended up releasing during his life. But there were still a few tapes, most of which got paired with beats and unlikely collaborators on Born Again and Duets: The Final Chapter. Each have decent tracks on them — “Dead Wrong,” a duet with Eminem, is especially impressive — but most of them don’t seem like the types of songs Biggie would actually do.

Like Biggie, Kurt Cobain didn’t record a whole lot of music he didn’t release (and the stuff that was left in the vault was left there for an excellent reason — they weren’t very good). But bootlegs were being widely circulated and the fans were hot for product, so Courtney Love released the live album From the Muddy Banks of the Wishkah in 1996 and With the Lights Out in 2004. The live album is decent if a little ramshackle, but the box set is a bit of a mess. While the DVD footage of Cobain jamming to Led Zeppelin’s “Immigrant Song” at Krist Novoselic’s mother’s house is a fascinating artifact, it doesn’t make up for the three discs worth of sloppy outtakes and poorly-produced demos. The one truly great song — the posthumous single “You Know You’re Right” — isn’t even on the box set (it appeared on the hits compilation Nirvana in 2002), but the pre-Nevermind studio session tunes “Oh, the Guilt” and “Return of the Rat” are both interesting and catchy.

So Jackson probably faces an uphill battle. Depending on who is in control of the legacy, the quality of the work will likely be wildly inconsistent. Plus, it’s still unclear just how finished these “songs” are. But one thing is for sure: They will see the light of day and will, in some ways, dictate Jackson’s musical legacy and perhaps make up for the creative hiccup that was Invincible.