Conan O'Brien recalls passing on hiring Ray Romano a year before his breakout sitcom success

Before Ray Romano became a household name with the sitcom Everybody Loves Raymond, he applied to be a monologue writer for none other than Conan O'Brien.

On the latest episode of his Conan O'Brien Needs a Friend podcast, O'Brien recalled the time he passed on hiring the Emmy-winning actor and comedian just one year before he hit it big on network television when the topic turned to missed opportunities.

Related: Ray Romano doesn't want an Everybody Loves Raymond American reboot: 'I'm just a little protective'

“Ray Romano wanted to be a monologue writer for my show,” shared O’Brien. "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.” O'Brien, now 61, was in his early 30s at the time and the host of Late Night With Conan O’Brien when he met with a "real nervous" Romano.

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“I just kind of said that your stuff is great but we didn’t have an opening,” recalled O'Brien. "So he goes from that experience to, maybe a year later, getting Everybody Loves Raymond and becoming this monolithic TV star."

O'Brien recalled running into Romano years later and the Parenthood actor telling him that he was "really bummed" to have lost out on the job opportunity. "I’m like, ‘What are you talking about? Do you realize what we pay monologue writers?'” O’Brien, who does a solid Romano impression, said with a laugh. “Ray, Ray, hello! Ray, you’re Ray Romano. That doesn’t happen if you’re with me writing!’”

Related: Ray Romano trolls Friends fans at Hollywood tour: 'Everybody Loves Raymond filmed on Warner Brothers too!'

Romano found great success as sportswriter Ray Barone in the CBS sitcom, centered on the everyday life of the sports columnist and his dysfunctional family. It ran between 1996 and 2005 for nine seasons and also starred Patricia Heaton, Brad Garrett, and the late Doris Roberts and Peter Boyle. Romano won three Emmys for his work on the show. His recent credits include shows No Good Deed and Bupkis, plus Martin Scorsese's The Irishman.

O’Brien hosted Late Night with Conan O’Brien from 1993 to 2009, which led to a brief stint on The Tonight Show before he hosted Conan from 2010 to 2021. He'll host the Academy Awards for the first time on March 2 in Los Angeles, two months after wildfires devastated the city.

“It’s not the easiest assignment I’ve ever had but I’m embracing it," O'Brien told The Hollywood Reporter at the Sundance Film Festival last month. "And it’s not about me, obviously. This is a moment for all of us to step back and say, ‘Be humble.’ Just be humble and say, ‘This is a massive moment. This is a terrible thing that’s happened in Los Angeles.'"

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