This week, Chief Keef — the Chicago drill rapper who ignited the hype around his city’s street rap scene in 2012 — made one of his most widely noted moves since the release of his Interscope debut Finally Rich in 2012, or, perhaps, since his subsequent dropping from the label last October. He released an elegiac ‘80s-pop-flavored single (interpolating the John Waite-penned “Missing You,” which would also be a hit for Tina Turner and Brooks & Dunn, respectively) which finds Keef sporting something of a country twang under a lightly cascading Auto-Tune patch. Gunshots and AKG sounds are built into the backbeat. It’s one of the most crossover-friendly recordings Keef has ever released, though it is, in so many respects, deeply odd in its conception.

Perhaps even odder, though, is the avenue by which the track has come to us: via FilmOn. This is Greek multimillionaire and perpetual entrepreneur Alki David’s chief venture of the moment: a free platform which streams live TV channels, movies, as well as original programming (there is now a “Chief Keef Live” station which plays his music videos 24/7). With its messy live chat feature and congested front page, the site looks like Adware waiting to happen. Keef apparently drew up a deal of some sort with David a few months back, but what a music “deal” would look like between a rapper and a legally suspect video streaming platform is hard to imagine. If there’s any pattern David has shown throughout his chequered career, it’s a propensity for unpredictability (this is, incidentally, a virtue of Keef’s). However, one of the offshoots of this personality trait — at least in David’s case — is a sporadic disregard for sound business practices. This could obviously lead to more career roadblocks for his new signee.

By way of explanation, here are five of the strangest tidbits we know about Alki Davis, who should definitely be more widely recognized as one of the entertainment industry’s strangest anomales.

1. He’s the heir to a Coca-Cola fortune.

Good morning #beverlyhills90210 #doberman

A photo posted by Alki David _ Beverly Hills (@alkidavid) on

David has never had to worry about money. His family (from the ethnically Greek population of Cyprus) owned Coke bottling companies all over the world. He had an upbringing congruous with being from a rich and powerful family, constantly moving across Europe, before ending up at notorious hippie school, Bennington in Vermont.

2. He’s been active as an actor and film director.

Though he’s made his greatest mark (or rather, stirred up the most controversy) as an entrepreneur freeloading off of the TV industry, he spent some time before the streaming boom of the ‘10s working in movies. He shared the screen with Jason Statham in The Bank Job. More importantly, though, he indulged in some Tommy Wiseau-esque/real-life Bowfinger pet film projects (he wrote, produced, starred and directed, of course): 2004’s Freediver and 2007’s Fishtales. Both were inspired by Davis’ own love of deep diving and look like probable lost classics. See additional coverage at Divernet.

3. He engaged in scuzzy business practices at FilmOn, and landed a couple of big lawsuits.

David’s FilmOn company was sued by a cadre of the major TV networks for copyright infringement. David was retransmitting their programming in real time with pretty much no legislation to support his action. When another online TV streaming service, Aereo, found a route toward legality, David, as retribution, kept up his own illegal practices at new website BarryDriller.com, mocking Aereo founder Barry Diller. This went on until Diller, inevitably, served him as well.

@bradleycooperoffical

A photo posted by Alki David _ Beverly Hills (@alkidavid) on

4. In addition to FilmOn, he runs a site called BattleCam.com, which is a cam-to-cam site with some creepy original programming.

As far as we can tell, it’s a misbegotten lovechild of Chatroulette, YouTube and Crackle. As soon as you visit the page, you may find yourself confronted with live footage of people yelling and threatening to kill each other.

5. David also dares people to do crazy things, professionally.

Well, perhaps professionally isn’t the right word, but in 2010 he offered a million dollars to anyone who would streak President Obama. He once got a man to agree to be crucified live on FilmOn. You can catch some snippets of the mayhem, and glimpses of some of David’s motley cast of celebrity friends, in a new documentary about him, Lord of the Freaks, which is now available to watch at iTunes.

Photos via David A. Walega