Martini Shot

Those who lived in New York during the ’70s and ’80s knew to carry around “mugger money”: a small wad of bills kept handy on the assumption you’d eventually be mugged. While New York has improved since then, the concept of “mugger money” remains alive and well in Hollywood. The managers with non-writing producer credits, pilot directors with perpetual royalties, agents’ 10 percent and lawyers’ 5 percent — showbiz is built off people smart enough to get some for themselves. But, as Rob Long notes, with budgets shrinking and spending slowing, even the pickpockets are getting squeezed.  Transcript here. Learn more about your ad choices. Visit megaphone.fm/adchoices

In show business, “after the holiday” — Labor Day, that is — are the three magic words that make August a breeze and September feel like back to school. But for Rob Long, it actually does mean back to school, as he starts his second year in the Master of Divinity program at Princeton Theological Seminary, and comes one step closer to his goal of pitching a multi-camera comedy while wearing a priest’s collar. If Rob had his way, though, we’d all be back in the classroom. Why? If Disney, owner of Lucasfilm and Marvel, can’t reach young male audiences, then we all need a core curriculum — one with every installment of the Porky’s franchise, Caddyshack and Taken. Transcript here. Learn more about your ad choices. Visit megaphone.fm/adchoices

Industry jargon once separated the insiders from the posers. Rob Long remembers a network president who tried to talk the talk — pitching a spinoff with a cheery “bip bip bip” and some magician-like hand gestures. Cue hours of mocking behind closed doors. But the bigger joke may be on Hollywood itself: while words like “showrunner” have gone mainstream, the actual craft of making television — running a room, shaping a script, building a show — is slipping away. And that matters a lot more than knowing the lingo. Transcript here. Learn more about your ad choices. Visit megaphone.fm/adchoices

Years ago, a well-known comic actor hosted an ill-fated late-night show that was canceled halfway through its 13-week run. But rather than leave town under a cloud of immense failure, this guy went to lunch. According to Rob Long, it was “the bravest lunch I’ve yet seen eaten,” and the comic was met with several well-wishers for his troubles. That’s because, as Rob says, people in Hollywood find failure exhilarating. “We wallow in misfortune,” he says. “We live to applaud the down-and-out. When people call you brave in the entertainment business, it’s almost always because you’ve done something that really sucked.” Transcript here. Learn more about your ad choices. Visit megaphone.fm/adchoices

Rob Long’s experience with Paramount goes back so far, he was there in the Gulf and Western days. He was there when Barry Diller fought Sumner Redstone for the company in 1994 for the company — and lost. He’s seen Viacom and CBS and everything in between. So as David Ellison takes over the storied company, Rob has a key piece of advice, if the young mogul is willing to listen: think small and watch Brad Pitt’s Moneyball. Because when you succeed at small, the big will take care of itself. Learn more about your ad choices. Visit megaphone.fm/adchoices

Walk up Madison Avenue, and there’s Hermès, Gucci and Tom Ford. Then, down in Soho is The RealReal, a luxury consignment store where you can find largely the same Gucci stripes, pebbled Hermes leather or giant Tom Ford zippers. The stuff is just a little used — and a whole lot cheaper. That’s the challenge Hollywood faces. A-list celebrities and studio-level comedy are just a click away on TikTok, YouTube or Instagram. It’s a little rougher around the edges, sure. But it’s free. So what’s Rob Long’s solution for Hollywood? Let him tell you. Transcript here. For more entertainment news, subscribe to The Ankler. Learn more about your ad choices. Visit megaphone.fm/adchoices

Stephen Colbert’s out, Greg Gutfeld’s in, and late-night TV is a shell of its former self. Rob Long breaks down what went wrong, why Johnny Carson wouldn’t survive 2025, and how Kimmel, Stewart, Meyers, and Oliver turned late-night into political homework at bedtime — while fighting over the same half of the audience. But Rob doesn’t blame a certain president for the Late Show cancelation. He blames the thing that always forces showbiz’s hand: money. Transcript here. For more entertainment news, subscribe to The Ankler. Learn more about your ad choices. Visit megaphone.fm/adchoices

Recording from Botswana, Rob Long figured he was as far as he could get from the chaos of showbiz. But it turns out that the wild African plain is a lot like Hollywood. Directors? They’re the Cape buffalo: loud, bossy and always wearing a headset (he’ll explain). Buzzards are akin to agents (no disrespect to either). And writers are rhinos — kind of prehistoric, not always strategic and endangered. Hey, even the sound of relief when Superman pulled in a $217 million opening weekend has a safari counterpart. But on the savanna, respite doesn’t last. It’s always back to getting stalked and eaten. Kind of like Hollywood. And the old lions better watch out.  Transcript here. For more entertainment news, subscribe to The Ankler. Learn more about your ad choices. Visit megaphone.fm/adchoices

Some debates are nuanced. For Rob Long, this isn’t one of them: Star Wars: Episode I — The Phantom Menace is a disaster, from the pod racing to Jar Jar Binks. No amount of revisionist history can make George Lucas’ Star Wars prequel any less disappointing. Yet Rob once had a meeting with a brilliant, respected man who claimed it was his favorite Star Wars film. Did Rob laugh in his face? No. He smiled and moved on. Because a lesson, in Hollywood and life, is that even if you can’t fathom your audience’s taste, mocking them for what they like rarely helps. Transcript here. For more entertainment news, subscribe to The Ankler or apply to The Ladder, a members-only hub for early career entertainment professionals. Learn more about your ad choices. Visit megaphone.fm/adchoices

As Rob marks a milestone birthday while traversing France, his thoughts drift — as they often do — from real life to showbiz. Gone are his days of being 24 years old, writing for 20 million viewers on Cheers. In their place: streaming “drops” that sound more like bodily functions than cultural events. But amid all that change, one rule still holds: If the laughs are flowing, showbiz is worth betting on. Transcript here. For more entertainment news, subscribe to The Ankler or apply to The Ladder, a members-only hub for early career entertainment professionals. Learn more about your ad choices. Visit megaphone.fm/adchoices

Keith McNally isn’t in showbiz, but he might as well be. Whether you’re dining at Balthazar or, like Rob, a frequenter of Minetta Tavern, it’s all lights, noise and timing. The food matters, but it’s the vibe that keeps people coming back — and the same goes for Hollywood. It’s not just plot and characters; it’s atmosphere, tone and letting the audience feel at home. Transcript here. For more entertainment news, subscribe to The Ankler or apply to The Ladder, a members-only hub for early career entertainment professionals. Learn more about your ad choices. Visit megaphone.fm/adchoices

If a joke falls flat, you’ve got two options: fiddle with the set-up or adjust the punchline. That’s comedy writing 101 — unless you had George Wendt. As Norm on Cheers, George’s timing, presence and even just how he walked into the bar got a laugh. But Norm was a lovable loser, while George was just plain lovable. And for writers like Rob, lucky enough to work with him, George was the secret third trick to make any joke land. Transcript here. For more entertainment news, subscribe to The Ankler or apply to The Ladder, a members-only hub for early career entertainment professionals. Learn more about your ad choices. Visit megaphone.fm/adchoices

The best TV shows are like the best restaurants, says Rob Long: familiar, comforting, and just stylish enough. Not everything needs to be a tasting menu or guilty junk — sometimes you just want a steak, buttered broccoli, baked potato and a laugh. So in this era where prestige and junk reign in both food and TV, Rob asks, where are all the Hillstones and Houston’s? Transcript here. For more entertainment news, subscribe to The Ankler or apply to The Ladder, a members-only hub for early career entertainment professionals. Learn more about your ad choices. Visit megaphone.fm/adchoices

This week, Rob wakes up spinning — literally — and ends up in the ER being evaluated by what appears to be the cast of Grey’s Anatomy: Gen Z. It wasn’t a stroke (spoiler), just vertigo, but that doesn’t stop Rob from noticing these physicians seemed to behave a little too much like TV doctors from ER, House or Chicago Hope — all of which gave Rob his own hope: TV really does still matter. Transcript here. For more entertainment news, subscribe to The Ankler or apply to The Ladder, a members-only hub for early career entertainment professionals. Learn more about your ad choices. Visit megaphone.fm/adchoices

As President Trump involves himself in showbiz finances, Rob Long raises the problem of what happens when government gets involved in Hollywood spreadsheets: Everyone above the line gets a raise because A. money is fungible; and B. greed. And below the line? Taxpayers in whatever state is offering cash-back goodies end up paying for second season salary bumps for the cast and the producers.  Transcript here. For more entertainment news, subscribe to The Ankler or apply to The Ladder, a members-only hub for early career entertainment professionals. Learn more about your ad choices. Visit megaphone.fm/adchoices

Time was when networks would land a major star, with the next step finding a writer with “auspices” — an industry term for somebody proven, with a hit show already on air. The only issue? Those successful writers often couldn’t write. In spite of that, those series sometimes became massive hits. Which is why Rob Long wants to keep optimism alive. After all, as he says, “Hey, could work.” Transcript here. For more entertainment news, subscribe to The Ankler or apply to The Ladder, a members-only hub for early career entertainment professionals. Learn more about your ad choices. Visit megaphone.fm/adchoices

Like Rob Long’s old Subaru, show business is leaky and can emit a toxic cloud — but it works. That is, until Silicon Valley strides in and tries to plug up the holes with things like “ad-free offerings” and an “all-inclusive monthly price”. What the tech overlords don’t get, though: It’s all those wires and oil and grime that keep the engine running. Transcript here. For more entertainment news, subscribe to The Ankler or apply to The Ladder, a members-only hub for early career entertainment professionals. Learn more about your ad choices. Visit megaphone.fm/adchoices

No matter how successful you are, the pitching never ends. Even the most seasoned TV creator has been known to melt down in front of their G-Wagon when they can’t land a greenlight: “Why don’t they just say yes?” Silicon Valley tech giants thought they could disrupt the “terrible business” of entertainment — less buying and selling, more ownership and verticality — which led to the streaming wars, and now a contracting industry where “the yeses just aren’t coming.” Transcript here. For more entertainment news, subscribe to The Ankler or apply to The Ladder, a members-only hub for early career entertainment professionals. Learn more about your ad choices. Visit megaphone.fm/adchoices

There are two keys to making money in showbiz: make a hit, and make it easy to watch and find. In other words, make the experience more like shopping on Amazon. Easy is why kids are on YouTube, Rob Long is watching The Gilded Age in TikTok snippets and why Amazon makes being online a seamless experience — except on Prime Video. Transcript here. For more entertainment news, subscribe to The Ankler or apply to The Ladder, a members-only hub for early career entertainment professionals. Learn more about your ad choices. Visit megaphone.fm/adchoices

Rob Long recently sold all the old junk from his house: airplane bottles of Dutch gin, a Yemeni incense burner, asparagus tongs and two boxes of computer cables, naturally. Refreshed and ready to begin a new chapter, Rob thinks studios need a similar garage sale with each other’s libraries. Offer up titles, make some swap deals — and reset the whole system, from the IP up. Transcript here. For more entertainment news, subscribe to The Ankler or apply to The Ladder, a members-only hub for early career entertainment professionals. Learn more about your ad choices. Visit megaphone.fm/adchoices