His record company famously paid his prison bail money in exchange for three albums.
But that's not the only artistry Tupac Shakur was working on from his prison cell because a graphic love note that he sent in 1995 is now proving extremely lucrative.
The late wordsmith reportedly penned a letter so sexual 'it makes 50 Shades Of Grey look like a Disney flick' - and it's expected to fetch $25k at auction on Monday.
Twenty years after the rapper was murdered in a drive-by shooting, the handwritten letter, published by TMZ, is being released by Goldin Auctions.
The explicit content features lines like: 'Ever been tied to a bedpost and licked like a lollipop?'
In the letter Lothario Tupak promises to leave the recipient 'shaking and quivering' by the '12 positions of lovemaking'.
The rap artist also teases with blindfolds, bubble baths, oily massages in his reply to her original 'passionate letter'.
Tupac signs off 'Until the end of time, 2pac' which became the name of his seventh studio album and third posthumous album.
The last time a letter written by Tupac was auctioned at Goldin Auctions, it was sold for $172,725, despite an early bid price of $11,000.
A 'household name' was reportedly outbid for the four-page, double sided letter, entitled 'Is Thug Life Dead?' and written during his time at New York’s Clinton Correctional Facility.
During his jailtime, Tupac signed a contract with Death Row Records's Suge Knight for his bail money.
The $3.5 million-plus contract, which is three pages long, bound him to make three more albums.