Ray Romano Applied to Write for Conan O’Brien — And Didn’t Get the Job
Everybody loves Raymond except for Conan O’Brien.
Before Ray Romano hit it big with his titular sitcom, he was just another working stand-up comic in search of a steady paycheck. “He wanted to be a monologue writer for my show,” Conan told Adam Scott on the Conan O’Brien Needs a Friend podcast. “Great comedian, great joke writer.”
The problem for Romano: Late Night With Conan O’Brien didn’t have an opening at the time. “But he had a good packet and people knew him,” said Conan, “so I met with him.”
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O’Brien was only 32 years old or so. Romano was about six years older, but in show business experience, O’Brien was the veteran. In his vague recollection of Romano’s interview, the comedian was visibly nervous. “I just said that your stuff is great, but we didn't have an opening.”
It was a sliding-door moment for Romano. Let’s say O’Brien found the money and hired the comedian to write his monologue jokes. Then what goes down next — Romano lands Everybody Loves Raymond a year later — likely never happens at all. As the saying goes, it’s better to be a monolithic sitcom star than an anonymous comedy writer throwing punchlines at the wall.
Or is it? O’Brien remembered running into Romano years later. O’Brien imitated Romano’s nasal delivery as he recounted the story: “So I was really bummed I didn’t get that job.”
O’Brien was incredulous. “What are you talking about?” he admonished Romano. “Do you realize what we pay monologue writers?”
“Was it me?” Romano responded.
O’Brien couldn’t believe the comedian was holding on to that failed audition in the wake of his blinding sitcom success. “Ray! You’re Ray Romano! That doesn’t happen if you’re with me writing!”
Didn’t Romano realize he was profoundly wealthy, laughed Scott.
“Because of your greatness, you can buy and sell me 35 times!” said O’Brien.
“I know,” Romano whined in O’Brien’s retelling, “but I think I could have done it.”
Instead, another late-night host, David Letterman, gave Romano his big break. “I don’t want to make this out to be more than it is, but my life has been affected more by David Letterman than anybody else’s,” Romano told the Hollywood Reporter in 2015.
In addition to giving Romano a deal to develop Everybody Loves Raymond, Letterman “was very supportive in helping to convince CBS to buy the show,” the comic remembered. “I knew that he enjoyed when I went on the show after that because he was a fan. That’s all I needed! It always felt good knowing that he believed in me.”
Without Letterman offering him a job, Romano explained, “I’d be your Uber driver today.”
