Awards shows are so glamorous that you play it safe to ensure you're part of the 'in' crowd

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 pants. 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.

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But in my mid-30s, I somehow finagled 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.

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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.