Some folks have to take the long and winding road to the top. We can't all have millionaire producers for fathers. There are definitely tiers of showbiz success, and if you're not born towards the pinnacle, it can be tough to scrape and claw one's way up the ladder. Moreso, without a ringer already in the game, it's tougher still to know where the next rung is. 

Ray Romano wasn't lucky enough to be a nepo baby. What he did have was a strong work ethic and a great sense of humor. More than any of his peers, Romano knew how to find the relatability of life's familial foibles. He gathered pieces of his home life and repackaged them for the stage. But the difference between a workhorse standup and a sitcom superstar is a canyon. 

In a 2019 interview with NPR's Terry Gross, Romano recounted his beginnings, making a living for himself and providing for his family before things really took off.

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And here's where I was. I was—I had been doing stand-up for 11 years. I did Johnny Carson in 1991. I did Leno a couple times. I did every stand-up show they had, Evening At The Improv, MTV— all those shows. I had my own HBO half-hour, and I loved doing it. I loved doing stand-up. I was happy to be doing what I loved, but I kind of reached a plateau, I guess, of where I was going to go. And if that's all I did for the rest of my career, you know, it's— it doesn't suck to be doing what you love to do. 

This in itself is hugely commendable. That kind of standup success is nothing to sneeze at. A comedian who's so adept at their craft that they can raise a family off their earnings is an increasingly rare thing. However, it took an industry insider to recognize that Romano could be more.

And Letterman, after I'd done my Letterman set, I kind of thought, well, that was a really good set. So let's see if it had— you know, maybe somebody? And it was Letterman. It was Letterman who was watching from 20 feet away.

At the time, Letterman wasn't just a talk show host. In addition to all the relevant experience that made him the man for that job, Letterman was also the founder of Worldwide Pants, a production company looking for new projects. It was the same eye for booking talent that helped Letterman and his cohorts recognize that Romano was ready for the next stage in his career.

And they called me. And I remember my wife saying, Rob Burnett's on the phone. I was in the backyard. I don't know what I was doing. I was hosing off the kids. And I picked the phone up. I was kind of surprised. And he said, listen, Dave liked what he saw. And so we just want to— we just want to say, I just want to tell you that we're interested. So let's see what happens. Just know, don't— before you sign anything else with anybody else, we're interested. And then, right away— I told them right there, nobody's— there is nobody else. You know, if you're interested, I'm interested. And sure enough, we signed a deal. And here I am.