Martini Shot

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

The podcast dives into the clash between Hollywood's luxury and the authenticity of social media content. It highlights the struggle A-list celebrities face against the free, relatable entertainment found on platforms like TikTok. A prominent writer reflects on the vibrant storytelling potential of 1980s New York, urging creators to draw inspiration from their dynamic surroundings. Ultimately, the conversation suggests that Hollywood might benefit from embracing real-life narratives rather than strictly competing with easily accessible online creations.

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