Conan O’Brien Passed on Hiring Ray Romano as a Monologue Writer 1 Year Before His Breakout Success on Everybody Loves Raymond

Conan O’Brien is opening up about something that just wasn’t meant to be.

On a recent episode of his SiriusXM podcast, Conan O’Brien Needs a Friend, the comedian revealed a funny story from when he first met Ray Romano in the ‘90s. Before Romano had his big break with his show Everybody Loves Raymond, he had asked to work for O’Brien — but got turned down.

“Ray Romano wanted to be a monologue writer for my show,” O’Brien, 61, recalled. “Great comedian, great joke writer. We didn’t have a slot, but he had a good packet and people knew him, so I met with him. He came into my office and, you know, at the time I’m like 32 years old.”

Going on to say that he only “vaguely” remembers the interaction, O’Brien noted that Romano “was real nervous.”

“And I just kind of said that, ‘Your stuff is great but we didn’t have an opening,’” he explained. “He goes from that experience to maybe a year later getting Everybody Loves Raymond and then becoming this monolithic TV star.”

“I remember later on running into him and [him] saying, ‘Ah, so I was really bummed I didn’t get that job,’” O’Brien laughed. “I’m like, ‘What are you talking about? Do you realize what we pay monologue writers? Ray, Ray, hello! Ray, you’re Ray Romano. That doesn’t happen if you’re with me writing!’”

Romano, 67, found massive success during the nine-season run of Everybody Loves Raymond from 1996 to 2005. He is also well known for being the voice of Manny in the Ice Age franchise and, most recently, starring in No Good Deed alongside Lisa Kudrow.

In December, Romano and Kudrow opened up to PEOPLE about bonding over both being ‘90s sitcom stars. “It was definitely something we could talk about. We had a lot of downtime. And we did swap stories and compare,” Romano said.

Kudrow, who played Phoebe Buffay in the iconic series Friends during its 10-season run, shared that she “was curious” to ask Romano questions about his experience during that time, even telling him: “I know what our set was like, what was [yours] like?”

“We were on the same lot,” she noted. “They were on the stage that we had the first season.”

“That was fun,” Romano continued. “It was a cool feeling, all the things you were saying without admitting it. We weren’t admitting to ourselves, ‘I’m a big sitcom star, and you’re a big sitcom star,’ but we understood this is kind of unique and cool.”