Michael Jackson — Michael
The great Michael Jackson cash-in started long before his untimely death in 2009, of course — his first “Greatest Hits” compilation was released in 1975, and they came thick and fast over the years after, particularly in the 2000s, when it had become clear that Jackson’s best days as an artist (not to mention a functional human being) were long behind him. HIStory, Number Ones, The Ultimate Collection, The Essential Michael Jackson, King of Pop, Gold, The Definitive Collection… they appeared pretty much every other year, often selling well into the seven figures. But it was this posthumous unreleased-tracks record that took the cake, appearing a year after Jackson’s death despite doubts that a) Jackson would ever have wanted this material to see the light of day and b) it was actually him who was singing on half the tracks. It was so bad, in fact, that we find ourselves actually agreeing with will.i.am on something.
Sid Vicious — Sid Sings
Sid “sings” only in the very, very loosest sense of the word — this would have been better titled “Sid Slurs Through an Awful PA at a Random Gig.” But that wouldn’t have sold many copies, would it?
The Notorious BIG — Born Again
As if subjecting the world to the execrable “I’ll Be Missing You” wasn’t bad enough, Diddy has milked Biggie’s legacy for all it’s been worth in the years since. The most egregiously awful example of this is Born Again, an album that picked up the Natalie Cole/Nat King Cole idea and ran with it, shoehorning unreleased Biggie vocal tracks together with verses by artists with whom he’d never collaborated in his lifetime (and, of course, the occasional rhyme from oh-so-altruistic label boss Sean Combs, who just happened to be promoting his debut solo record at about the time this dropped.)
Tupac Shakur, generally
Still, the milking of Biggie’s legacy pales in comparison with what’s been done to that of his erstwhile rival Tupac Shakur. The 2Pac barrel has been scraped pretty comprehensively since his death in 1996, and although his first posthumous release — The Don Killuminati: The 7 Day Theory — was completed during Shakur’s lifetime, everything since has been the usual assortment of unreleased scraps and cobbled-together tracks. It seems the public’s patience with such things has been exhausted — the most recent posthumous 2Pac release (2006 album Pac’s Life) sold exceedingly poorly.
Jimi Hendrix, generally
The king of the posthumous release. Hendrix released four albums during his lifetime, one of which was a live album. Since his death, enough material has been scraped together for ten more records, and that’s not even mentioning the myriad repackagings of his “real” albums.