Prince's career-long quest for control over ownership and distribution of his art led to a conflicted relationship with the internet. Like much of the rest of the world, however, he couldn't escape it completely — and on occasion, its technology and terminology even seeped into his songwriting.

A case in point is "Emale," the fourth track on the second disc from his 1996 album Emancipation. Recorded at a time when email use had yet to reach its saturation point and broadband internet access was still a sci-fi pipe dream for home users, the song includes a number of lyrical references to computers and online life — including a chorus revolving around the URL "www.emale.com," which eventually became one of the multitude of sites affiliated with or owned by Prince over the years.

While "Emale" was never widely considered one of Prince's major works — according to the Prince Vault, it was never even performed live — it offers an early reflection of his ongoing fascination with the dawning digital era. As fans are well aware, he took a number of early opportunities to utilize digital distribution, and was one of the first artists to use the internet as a vehicle for releasing new work, yet he was also keenly aware of its rapidly expanding potential for theft and copyright infringement.

In later years, Prince would often seem outright antagonistic toward the internet, issuing a flurry of cease-and-desists in response to a wide array of online content that sometimes referenced his work only indirectly — including his infamous decision to go after his own fans' sites in 2007.

Hear Prince Perform 'Emale"

Yet the ever-complex Prince was also fully aware of the internet's power as a tool — and he could be a playful email correspondent, as recalled in photographer Afshin Shahidi's 2017 book Prince: A Private View. In fact, according to Shahidi, he learned online acronym etiquette from the Artist, at one point picking up a lesson the hard way through an embarrassing gaffe.

"I didn't know all the different acronyms and stuff. I didn't know that LOL meant 'laugh out loud,'" wrote Shahidi. After being set straight by his wife, he realized he'd inadvertently used "LOL" on a number of inappropriate occasions with Prince, and eventually had to confess his ignorance.

"I started thinking back at all the emails I'd sent him where I had written 'LOL,' like where I told him what it would cost to do something," added Shahidi. "I told him [about the misunderstanding] a couple of years later. He cracked up and started shaking his head."