How to Write Emails Like a Hollywood Asshole

Making sure everyone knows you’re evil using text alone.

DISCLAIMER: No identification with actual humans or humanity or kindness or justice or goodness is intended or should be inferred.

I got a job on my first day in Los Angeles. It was a great opportunity, the kind people in small towns dream about while watching TMZ. Executive assistant to a powerful Hollywood agent, consigliere to a handful of the most famous people in the world. He was an endorsements agent, meaning that he handled multi-million dollar contracts between major brands and his stable of A-listers. In reality, he didn’t do much of anything besides say no. Or n[.

His lunch was my responsibility. He only consumed food from one of three or four high-end delivery restaurants on Sunset at the bottom of the hill. The orders were always strange and dispassionate. My favorite was a $27 turkey burger which he ordered with no bun, no sides, and lots of ketchup. He ate this hamster pellet of protein alongside a primordial green soup that he kept in a Tupperware container in the refrigerator, right next to the fresh botox injections.

Other things that were my responsibility to procure were a brown paper bag of anonymous “spices” kept in a mailbox on the Bird Streets, a whole pharmacy of medication for his aging dogs, and the more luxury type of Evian water (yes, there are two types). When his favorite grocery store had run out of this higher-end Evian, he sent me on an urgent mission to find more. I visited four stores in West Hollywood before emailing him a desperate apology, “I’m so sorry, they only have the other kind of Evian!”

His response? “ok.”

Of the many lessons I learned from this man, the most fascinating involved emailing. As someone who had come from the very straightforward emailing environment of the New Orleans legal world, the lackadaisical, almost infantile flavor of the Hollywood power email caught me as a total surprise. When someone was upset with me, or threatened by me, I was used to receiving a well-articulated treatise. Here was the total opposite. The angrier he was at someone, or the more he wanted to dominate them, the fewer words he used.

To his friends, the one or two wealthy women that he dined with at Chateau Marmont several times a week, he would offer one or two lines, usually all in lower case, often with a glib twist.

yesss, bitch

This was one end of the spectrum.

On the other end were business adversaries, powerful men and women in the fashion industry with their own sensitive egos. To them, his emails often consisted of a single word. If he was really threatened, it might even be misspelled.

Can we do a call at 12:30?

That was it. Signaling refusal, as if he was so busy, so incredibly, amazingly busy, that he could not even properly spell “no” before clicking send.

One time, the CEO of a major international clothing chain, a loud and proud Brit, was yearning for my boss’ approval to pay one of our B-list clients tens of thousands of dollars for a photoshoot. For whatever reason, my boss decided to show hhim a little bit of Hollywood hospitality. As the deadline for the release of the line approached, my boss became increasingly distant. The CEO would call the office line, which I would pick up, and my boss would tell me to say he wasn’t there. Then the emails flooded in.

Can we finally get a call on the books this week, this is urgent?

that won work.

What if we do this amount?

no thar wont work.

I’d really like to get this hammered out, how can we make this work?

lets touch base nxt wk.

It ended with the CEO having a meltdown on the phone with me, the king’s lowly assistant, acting as empathetic psychologist. Indeed, in four years in Hollywood, I have become quite familiar with the industry’s biggest fuck you: “lets touch base nxt wk.”

Though brevity, in my opinion, is the cruelest communique, sometimes circumstances did call for longer emails that could pack a more specific punch. These emails tended to seize upon some defining characteristic of the receiver, and would use that characteristic to deliver the dagger close to home. It was usually me on the receiving end of these special emails, as the boss tried his best to whittle me into the whipping boy that he needed.

How the boss learned I was interested in politics, or that I was interested in breathing, I have no idea, as I don’t think he made eye contact with me once for the entire three months I was there before being unceremoniously fired for “wanting the path to success to be too easy.”

I was instructed to buy a playground set. He had created two children via a host mother inseminated with his sperm. He was a Persian Jew (although the Hollywood power elite really constitute an ethnicity of their own, a very strong one that’s easy to detect once you’re aware that it exists), but the gaybies were blond haired and blue eyed, which suggested that he’d found the most Aryan host mother possible. Though they were only two and three years old, he would throw them $30,000 birthday parties at Chateau Marmont. When the male fell and hit his head on a piece of playground equipment at his private pre-school, the boss flew into a rage. “I want an entire new set of playground equipment by tomorrow!” he shouted, “The equipment there is old and disgusting! It’s dangerous!”

When I asked him about the size of the needed playground, he said one of his most common refrains, “Figure it out! You must be the dumbest person with a law degree I’ve ever met!” I called the school to inquire about the size of its playground. When he found out, he flew into a rage again. Wasn’t it obvious that it was supposed to be a surprise?

Forty-eight hours later, when the playground had not arrived, he was even more mad. I was in the preliminary stages of having an original playground set fabricated in China for a bargain $13,000 and shipped immediately by freighter, but my lack of communication was inexcusable. When I told him that it wasn’t ready yet, I was blessed with a surprisingly long email.

Imagine this was the Democratic Convention. You just lost.

by Isaac Simpson