the oscars are Sunday. Despite the fact that box office receipts are well below pre-pandemic levels, and despite the fact that this era of Hollywood has arguably been to art what Tropical Skittles are to haute cuisine, Hollywood’s stars will come out for a broadcast whose ratings should – if everything goes well – narrowly edge out “Wicked Tuna” on National Geographic.
I’ve never been to the Oscars. But back when I was a writer for “Last Week Tonight with John Oliver,” I got to go to the Oscars’ less-sophisticated cousin the Emmys five times. That was great, and not just because the tuxedo I bought at Sticky Rick’s Discount Tuxedos and Live Bait paid for itself after the third wear. The Emmys were the most glamorous experience I’ve ever had; for comparison, my second-most glamorous experience is probably the time I found half a hot dog on a bus. The whole thing was ridiculous in a fun way, like putting Jell-O down your And it helped me understand why TV and movies are less ambitious and more boring than they might otherwise be.
I got into comedy the typical way: by accident. When I was 24, I went to a standup open mic simply to interrupt the cycle of video games and internet “content” that’s typical for a guy that age. By my late ’20s, I was playing the top venues in my area, including Sticky Rick’s (Monday was Comedy & Crayfish night!).
From dreaming about making it to living the dream
Standup is not a glamorous life. You spend a lot of time in dive bars trying to convince the owner that your little clown show is a better draw than a Big Buck Hunter machine. You often get paid in chicken wings and/or beer, which is why comics typically live about as long as a great dane.
You dream of “making it,” but you don’t really think you will. For me, dreaming about “making it” was like fantasizing about marrying a mermaid and living under the sea.
But in my mid-30s, I somehow finaged a job on John Oliver’s show. Eighteen months later, I found myself at HBO’s Emmys party, rubbing elbows with Mel Brooks and the cast of “Game of Thrones.” The day before, I had flown first class for the first time in my life and checked into a hotel so fancy that I took a picture of the soap. HBO paid for everything. People shoved free food and drinks into my hands the entire weekend, so I drank like a frat pledge and ate enough free shrimp to shame a humpback whale.
The service at an awards show is so good that it makes the “Downton Abbey” staff look like Frontier Airlines’ B-team. If you even think “I’d like some water,” a fresh-faced 20-something will jump out from behind a shrub and hand you a bottle. The bottle will be square, because apparently only hayseeds drink cylindrical water. Drivers, waiters and bellhops are all absurdly nice, because you might be far more important than you look – after all, anyone in Hollywood could be Daniel Day-Lewis researching a role. Altogether, the Emmys provided a level of being spoiled normally known only to child emperors and the bad kids in “Charlie and the Chocolate Factory.”
My point is: My quality of life after I broke into entertainment was ludicrously higher than it had been before. And that made me desperate to stick in the industry. I became reluctant to take risks, swim upstream or generally rock the boat in any way. The truth of the matter is that a field that can raise a typical person’s standard of living by several orders of magnitude is not conducive to challenging or risk-taking art.
America is in danger of falling apart. We need to act now before it’s too late.
Some people in entertainment take risks. Those bold few should be commended; they’ve shown bravery that I was unable to summon while I was being bribed into complacency by complimentary seafood. When Hollywood makes something original – and they occasionally do – I tip my cap to the swashbuckling daredevils who ran the gauntlet of hyperventilating lawyers and backside-covering studio executives to get the project made.
Staying ‘in’ means playing it safe
But most people in entertainment avoid risk. That’s not because they’re notably craven or cowardly; they’re the same amount of craven and cowardly as most people. But they’ll play it safe because the system doesn’t reward risk-taking. Every entertainment project is a big, fat question mark, so when you have to choose between producing a big, fat question mark that might get you cast out of Eden and a big, fat question mark that won’t, most people will opt for safety and make “Star Wars Episode XXIV: Dude, Where’s My Millennium Falcon?”
It’s not realistic to expect Hollywood to regularly make challenging content. And that’s because not many people can resist the status, money and general fanciness that a career in entertainment provides. I certainly couldn’t; I spent every minute of my six years in TV terrified that I’d get booted back to slinging jokes at Sticky Rick’s. If John Oliver had told me, “Write a piece about how Alan Alda is the ‘Zodiac Killer’,” I would have done it. Because the gap between where I came from and where I found myself was just too large.
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Inevitably, a few Oscars speeches will reference the leading role that movies supposedly play in social progress. That will be true in a few instances, but for the most part it will be BS. Hollywood should stop presenting itself as some sort of cultural vanguard; the TV and movies they make rarely push boundaries and frequently confirm what’s already been deemed acceptable. That’s not because folks in Hollywood are bad people; it’s because they like free booze and shrimp just as much as everyone else. People call Hollywood a “dream factory” because it is: It produces a standard of living that most people can only imagine. But it’s not really possible to be a Dream Factory and an Edgy, Boundary-Pushing Art Factory at the same time.
Jeff Maurer was formerly Senior Writer for Last Week Tonight with John Oliver. He currently writes a Substack newsletter called “I Might Be Wrong.
George is Digismak’s reported cum editor with 13 years of experience in Journalism