Martini Shot

In 1923, to promote Harold Lloyd’s Safety Last!, the studio didn’t buy ads — it bought a spectacle. They hired Harry F. Young, “The Human Fly,” to scale a Manhattan hotel in honor of the film’s most famous stunt (you know the one). He made it about 10 stories up before falling to his death — and right into the morning papers. It was, in every sense, earned media. A hundred years later, Rob Long finds that not much has changed in Hollywood’s endless climb for attention — except, maybe, the safety net. Learn more about your ad choices. Visit megaphone.fm/adchoices

When Rob Long was 18, a dentist said his wisdom teeth had to go. His father told him to hang up the phone: “The whole wisdom tooth thing is a scam.” Forty years later, Rob's fine — mostly. And now, watching David Ellison try to merge Paramount and Warner Bros. in an industry where economies of scale rarely if ever succeed, he sees the same impulse at work: a painful, costly procedure masquerading as progress.  Transcript here. Learn more about your ad choices. Visit megaphone.fm/adchoices

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

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