Why Conan O’Brien Rejected Ray Romano Just Before ‘Everybody Loves Raymond’ Took Off

Conan O’Brien recently shared a memorable story about Ray Romano during a podcast. Years ago, Romano wanted to join O’Brien’s team as a monologue writer. O’Brien, who was about 32 at the time and just getting his start on Late Night with Conan O’Brien, remembered meeting Romano, who was understandably nervous for the opportunity.

“He had a strong writing packet and was already known in comedy circles,” O’Brien recalled. “But we didn’t have an opening.” A year later, Romano became a household name starring in Everybody Loves Raymond, which ran from 1996 to 2005 and showcased the comedic ups and downs of a Long Island sports writer.

Years later, the two crossed paths again. Romano admitted he was disappointed about not getting the job. O’Brien responded with a laugh, reminding him, “You’re Ray Romano! You wouldn’t be the superstar you are if you were writing for me.”

O’Brien has had a successful career in late-night television, hosting Late Night with Conan O’Brien from 1993 to 2009, briefly helming The Tonight Show, and later running Conan until 2021. He is set to host the Academy Awards for the first time soon.

Regarding his upcoming gig, O’Brien mentioned the timing is challenging due to recent fires in Los Angeles. “It’s not the easiest assignment,” he said, emphasizing the need for humility in light of the circumstances. “This is a moment for all of us to step back and say, ‘Be humble,’” he added.