The Most Valuable Characters From The Dueling Fyre Fest Documentaries

Senior Editor
01.25.19 9 Comments


There aren’t many subjects about which the world needs two simultaneous documentaries (Fyre Fraud, on Hulu, and Fyre, on Netflix), but the Fyre Fest is one of those things. I watched both and would recommend it to anyone. Hell, I’d probably watch a third. Through it all, we laughed, we got angry, and we met some wonderful characters. Here are some of the characters, both hero and villain, who made it such a compelling watch (and yes, I left out Fyre Fest founder Billy McFarland, who is basically the main character in both).

Ja Rule

Role In The Saga: Billy McFarland’s right-hand man.

As Seen In: Both documentaries

Contribution To The Story: For some reason, every tech evangelist needs a hip-hop guy to give him street cred, which is why is always speaking at tech conferences and Common does commercials about the incredible techno future. It’s so perfectly fitting that when an off-brand Zuckerberg was looking for his he found Ja Rule.

Best Moment: Probably a tie between Ja’s favorite toast (“here’s to living like movie stars, partying like rock stars, and… Billy? {…f*cking like porn stars}”), which would’ve gotten you jeered at a frat party in 2002, and the conference call moment in Fyre when someone asks “Isn’t that fraud?” and Ja answers “Nah, it’s just, like, false advertising.”

Keith The Crazy Pilot/Voice Of Reason

As Seen In: Fyre on Netflix

Contribution: Keith becomes one of Billy McFarland’s fixers in the Bahamas, and we’re first introduced to him as the nutty guy who says he learned to fly with Microsoft flight simulator. He eventually becomes the unlikely voice of reason, who actually camps on the island in a tent to see whether it’s feasible (it isn’t) and comes up with a plan (sleeping on cruise ships) to solve the inherent infrastructure problem. Naturally, he gets fired for not thinking positively enough. (Lots more on the tech world’s cult of “positive thinking” here.)

Notable Moment: “You ruined my sewage calculations,” Keith says when Billy (or was it Ja Rule? Unclear) spills beer on the blueprints he’s using to explain why the festival needs more bathrooms.

Delroy The Bartender

Role: Delroy is the bartender at MacDuff’s on Norman’s Cay, the island once owned by Pablo Escobar that Billy McFarland tries to buy but is kept from doing so when he immediately mentions Escobar in the Fyre ads, in violation of his agreement not to. Delroy becomes another of Billy’s local fixers.

As Seen In: Fyre Fraud on Hulu

Contribution: Delroy is easily my favorite character in either documentary. He takes an amused, detached-but-pleasant, “I don’t think you’re gonna pull this off, dog, but I’m happy to see you try” approach to the whole thing. You get the feeling Delroy has seen more than his fair share of assholes like Billy before, and is happy to keep pouring them drinks and nod at their grandiose bullshit if it will make for an interesting story. Delroy is the ultimate everyman hero.

Notable Moment: “Who the f*ck orders two million dollars worth of booze, dawg?”

The “Social Media Strategist” (Vicky Segar)

Role: Social Media Strategist

As Seen In: Fyre Fraud

Contribution: Vicky is there to explain social media strategies and companies and how the influencer marketing game works. I don’t know if I’d quite call her a “villain,” but she’s definitely there to explain things that everyone hates.

Notable Moment: “I think influencers are actually really brave.”

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