"I know you’re a working-class stand-up from Boston. You do stand-up. You make, maybe, eighty-thousand dollars a year on club dates, but you’re on the back-nine of your career. Except for once and a while a special on cable, I think five years ago you probably peaked and now you’re waiting around wondering if something’s going to happen before it gets embarrassing. Am I right?"
Cue emotion-tugging piano, gently cascading in the background.
"You don’t think you could do it. You think it’s over and you’re afraid to try. I mean, I get it, that’s normal, I’ve seen it. And I’ve seen it turn around. Let me offer you a proposal. You go back to New York. You get in shape. You lose about 40 pounds. I get you with Jackie Doll, who’s my main city man. He works with you, and then in about two months we do a test show… Jack’ll get you a small studio. You’ll do a monologue, you’ll do a couple of interviews, and uh, if the test is good, I’ll put you on the air. And then if you’re a hit everybody’ll think I’m a genius and I’ll have saved the network about twelve million dollars. If America hates you no one’s going to blame me. We’ll hire Jerry Seinfeld to do the show, no harm no foul. But you’ll take the heat on all that. You’re gonna crack your head on the ceiling and you’re gonna go down. Probably for good.
Look, Louie. We’re talking about The Big Game here so forgive me if I use big terms. Here’s the reality. In ten years you’re going to be teaching comedy in a community college to support your kids and falling asleep to the ‘Late Show with Jerry Seinfeld’. You’re circling failure in a rapidly decaying orbit. That’s the reality as we talk now. But you can change that. It’s in your power to change that. Yes, you’ll have to work hard, you’ll have to do things you haven’t done before, and still your chances are very slim. But you could change it. I’m gonna ask you one more time: David Letterman is retiring. Do you want his job?"
What happened here goes beyond recognizing when you’re being lucky and being given. This is someone flat out asking if you’re fundamentally, at your core, willing to accept complacency, or are willing to risk becoming a success. Is Louie willing to let his time run out, or will he risk such a banal-yet-comforting future for a chance at greatness? Absolutely, the risk is tremendous, and it could all fail miserably, leaving him worse off than he is now. Or it could work. Everything here relies on “could.” What could your future be if you didn’t shut the door to possibility? What could happen if you worked harder than you’ve ever worked, expanding your aim to areas you previously never even considered? What could happen if you risked becoming a success?