In 1990, Will Smith was twenty years old and considered washed up.
He’d had the big hit—“Parents Just Don’t Understand,” the Grammy, the video you can still picture. Then he spent all the money. Then he found out, apparently for the first time, that you have to pay taxes on money you spend. He owed the federal government something like half a million dollars. Jive had dropped him. No record deal, no acting career, and he had never acted in his life.
So when he took a sitcom, it was not a big break. In Andy Borowitz’s words, it was closer to: maybe I can pay my taxes.
Andy created that show. He sat down with me for an hour and a half, and this is the part where I tell you that I have interviewed a lot of people this year and this was one of my favorite conversations of the entire run.
Watch that. Watch it for the sweet potato pie story, which I am not going to spoil, except to say it involves a junior writer named Benny Richburg quietly telling his white boss that the Thanksgiving menu in the script was, let us say, not the menu—and what happened in the studio audience when they fixed it. Andy describes the reaction as “a nuclear weapon exploding.”
And watch it for the part where the network—every executive of whom was white and rich—kept giving notes because they related to the wealthy lawyer parents instead of to Will. They wanted Will to say “just kidding” after his jokes. Andy told the president of the network: you have all been to a black tie dinner, and the audience has not. They are going to relate to the kid making fun of the room.
It was the highest-testing pilot the network had that year.
That is one story. There are ninety minutes of them.
In the full conversation, Andy also explains what Fox News actually wanted when they booked him, which was not a comedian. He says the thing nobody with a network contract will say—“I am a Democrat, I’ve never pretended to be both sidesy”—and makes the case that equal-opportunity satire is a lie when one side is doing all the lying. We get into the life of a comedy writer, what he learned from Carroll O’Connor that he was still using twenty years later, and why a show that made hundreds of millions of dollars was never treated inside the building the way Friends was.
The whole thing is for paid subscribers. That is not me being precious about it. There is no advertiser paying for this show, no network, no corporate parent. There is a camera, a producer, an editor, and you.
Here is the pushy part, and I am going to be honest that it is the pushy part.
If you are already a paid subscriber: the next four paragraphs are not for you. Click the card above, pour something, and enjoy the whole ninety minutes. You are the reason it exists. Everyone else—
Our Democracy 101 back-to-school sale ends tomorrow night at 11:59 Eastern. That is about thirty hours from right now. Forty percent off your first year: $36 instead of $60. Three dollars a month. On Tuesday the price goes back to sixty and stays there until we have another reason to do this, which will not be soon.
You are reading this because you actually read us. You open the thing, you click the links, you have been around a while. You are, statistically, the most likely person on our entire list to enjoy the full ninety minutes of Andy Borowitz—and the one most likely to keep meaning to subscribe until the price goes back up on Tuesday.
Do it now. It is three dollars a month and it takes forty seconds.
Then go watch a man explain how a broke twenty-year-old rapper with a tax problem became the most likable person on television.
—Cliff
