Rob Long’s friend has a near-perfect system for staying in touch: a text every five weeks to the day, the wording on rotation, the calls auto-booked — friendship by tickler file, a little bit human and a lot robot. Naturally, Rob sets out to sabotage it. But AI in Hollywood is a much different, nuanced debate. From screenwriting manuals to the algorithmic clockwork of Law & Order, Rob believes that the one thing the machines can’t do is make a really interesting, unexpected mess. So we should.

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Clint Eastwood just turned 96 — older than the talkies, a man who’s been alive for every talking picture ever made. Which got Rob thinking about Dirty Harry and a 1952 thriller almost nobody remembers called The Sniper: same city, same crime, same rooftops, 19 years apart, and two completely different Americas. You can read the country off them like rings on a tree. Or, you can just write them off and refer to the films as “dated” — a grave mistake, according to Rob.

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Rob Long is watching a Satyajit Ray film on Criterion while eating ice cream and staring at his phone — which means he is, essentially, just eating ice cream. Rob is a pro at keeping his head down. Writers do it at auditions, following along with their own words instead of watching what actors are doing to them. Which turns out to be expensive, because the two actors who read “You’ve heard of me” as completely opposite character choices taught the writers something their script didn’t know yet. Heads down feels productive. Heads up is where the show actually lives.

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Rob Long has a favorite story about network upfronts: a television network, unable to decide which of three pilots to schedule, flew all three casts to New York on the same plane, collected focus group results mid-flight, and met them at the gate — whisking some into Manhattan and stardom, and sending the others home. It contains everything you need to know about Hollywood: extravagant spending, procrastination and cruelty masquerading as efficiency. But here’s the thing — the focus group never actually went away. It just moved to TikTok. And it’s been telling Hollywood exactly what audiences want since approximately 1994. They just won’t look.

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In Amsterdam last month, in front of a Dutch painting of a plump, nearly bald, angelic figure of indistinct gender, an old friend turned to Rob Long and said three words: “Hear me out.” It’s the great phrase that buys a few seconds of grace before you say something insane — along with its writers’ room cousin, not this, but. Oftentimes the ideas that emerge out of hear me out aren’t usable whatsoever. But Rob makes the case that its those risky Hear Me Out projects that the entertainment business runs on.

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Rob Long remembers Radford Studios — the working lot in Studio City where the parking sheet promised “premium” spots that never quite existed, the guard who couldn’t understand why you’d skip the Leave It to Beaver street for the fifth floor of the garage, and a writer friend who stumbled, mid-meltdown, onto the abandoned set of Gilligan’s Island. This week, news broke that Goldman Sachs — having seized the lot after Hackman Capital Partners defaulted on a $1.1 billion mortgage — is selling it to Netflix for a fraction of what Hackman paid in 2021. Turns out the premium parking wasn’t premium after all. It never really was.

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Rob Long is at a bar on a Monday night, pretending to pay attention to a conversation while secretly watching CBS’ The Neighborhood on a TV across the room, sound off. He predicts every beat of the episode anyway. A friend in the business says that’s exactly the problem with those shows. Rob disagrees — politely, and then less politely. Sitcoms are the same as they always are. That’s the point.

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There’s a lesson Rob Long learned early in his television career: When an actor has a problem with the script, the smartest thing you can do is nothing. Don’t talk. Don’t fix. Don’t explain. Just listen — because sometimes that’s all anyone really needs.

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The TV comedy writers’ room has a reputation as a creative paradise — funny people, good lunches, great jokes. That reputation is not wrong. It just leaves out the part where everyone is being systematically destroyed. Rob Long makes the case that the destruction is the point — that the specific cruelty available only to people who have been in rooms together for decades is what produces the trust that produces the comedy. Without it, you’re left with Zoom rooms and unfunny scripts.

Transcript here

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Rob Long has spent 30-plus years in the television business telling other people what’s wrong with their scripts. But the tables can — and often do — turn. Rob’s seminary classmate doing his first open mic informed Rob that his joke suggestions are, and this is a direct quote, “too wordy.” And Rob remembers the time a day player on one of his shows submitted a spec script for the very same show — titled, with magnificent audacity, “Billy Moves In” — and then proceeded to give Rob detailed notes on everything that was wrong with his series and how all of it could be fixed by the addition of his part. The lesson, such as it is: In this business, the note always lands, regardless of who’s delivering it. Even if it’s Billy. Even if it’s a seminary student. Even if they’re completely wrong. Which they were. Probably.

Transcript here.

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