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.”

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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.

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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.

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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.

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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. 

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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.

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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.

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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.

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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.

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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?

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