In the entertainment industry, it’s often the moments of “what could have been” that fuel the most captivating stories. Conan O’Brien, the sharp-witted late-night host, has been the driving force behind numerous iconic TV moments, but there’s one story from his career that still raises eyebrows. Conan O’Brien passed on hiring Ray Romano just before the comedian went on to create the iconic TV show Everybody Loves Raymond. What happened? How did this missed opportunity turn into one of the most iconic career decisions in television history?
In this article, we’ll dive into the circumstances surrounding Conan’s decision, Ray’s rise to stardom, and what could have been if these two comedic giants had crossed paths in the world of late-night television.
The Comedy Scene in the Early 90s: A Snapshot of Opportunities
The early 90s was a volatile time for comedians. Many were trying to carve out their niche, while late-night shows like The Tonight Show with Johnny Carson and Late Night with David Letterman set the stage for future stars. Conan O’Brien was emerging as a comedic writer, and Ray Romano was still an up-and-coming stand-up comedian.
At this point, Conan O’Brien was just starting his late-night career, with his writing experience on Saturday Night Live and The Simpsons. Meanwhile, Ray Romano was honing his stand-up comedy skills, still in the process of finding his voice. Both of them were on the edge of breakthroughs in their respective careers, and yet, fate almost didn’t align.
Conan’s Show: The Beginning of Late-Night Chaos
In 1993, Conan O’Brien took over Late Night after David Letterman left the show to launch The Late Show with David Letterman on CBS. The comedic style of Conan’s show was incredibly different from Letterman’s. His quirky humor, unique skits, and his “weirdness” was setting him apart from the more traditional late-night hosts. Conan was an unconventional choice, but he was beginning to make waves.
However, one thing that was missing from Conan’s show was a strong roster of recurring talent—people who could offer something distinctive to his comedy.
Ray Romano’s Struggle: From Stand-Up to the Small Screen
Ray Romano had been a rising star on the stand-up comedy scene, performing at clubs and getting noticed by comedy insiders. His brand of observational humor, based on his experiences as a middle-class guy trying to make sense of the world, was starting to get a lot of attention.
Romano was someone who appealed to audiences through relatability—his awkward delivery and self-deprecating humor made him a favorite among everyday people. But, in 1993, he was still struggling to break into the television industry in a meaningful way.
The Fateful Meeting: Conan O’Brien and Ray Romano Cross Paths
It all started with a meeting between Conan O’Brien and Ray Romano. At the time, O’Brien was looking for new talent to add to his show. Romano had recently made a name for himself in the comedy world, and there was a glimmer of potential for a possible collaboration. The two met, and, according to some reports, the encounter didn’t go as either of them expected.
Conan O’Brien, always known for his offbeat sense of humor, was skeptical about adding Ray Romano’s traditional comedic style to the mix. Romano, on the other hand, wasn’t sure how he would fit into Conan’s fast-paced, surreal late-night comedy. After the meeting, O’Brien decided that Romano wasn’t the right fit for the show, and so the partnership never materialized.
The Aftermath: Ray Romano’s Big Break
After being turned down by Conan O’Brien, Ray Romano continued performing stand-up and soon landed a deal with CBS for a sitcom—a show that would become Everybody Loves Raymond. The show premiered in 1996 and quickly became one of the most beloved family sitcoms of the decade. Romano’s portrayal of a relatable, neurotic husband trying to balance family life with a demanding career resonated deeply with audiences.
Ray Romano’s success with Everybody Loves Raymond made him a household name, earning him Emmys, Golden Globes, and widespread fame.
What Could Have Been: A “What If” Moment in TV History
While Ray Romano went on to become one of the most successful TV stars of his generation, many still wonder: What if Conan O’Brien had hired him? Could we have seen a different version of Late Night with Conan O’Brien—one that featured Romano’s awkward yet hilarious comedic style? Would the pairing of O’Brien and Romano have created a new dynamic in the world of late-night television?
The question of “what if” remains one of the most intriguing hypothetical scenarios in the entertainment industry. Had O’Brien taken a chance on Romano, the landscape of late-night TV might have been vastly different.
Ray Romano’s Career Evolution: From Stand-Up to Acting
Ray Romano’s journey into acting, especially as the star of Everybody Loves Raymond, marked a dramatic evolution in his career. Romano’s talent was not just limited to stand-up comedy—his ability to portray complex family dynamics and relatable characters set him apart. But it was his commitment to making his humor accessible to everyone that made him stand out.
After Everybody Loves Raymond ended in 2005, Romano’s career continued to flourish with voice roles in animated films like Ice Age and The Simpsons, along with critically acclaimed roles in series like Men of a Certain Age. Romano’s post-sitcom career highlights his versatility and staying power in the entertainment industry.
Conan O’Brien’s Evolution: From Late-Night Host to Comedy Icon
Meanwhile, Conan O’Brien’s own journey took him from late-night television to other successful ventures. O’Brien is known for his unique comedy style, which blends quick wit, surreal humor, and self-awareness. Over the years, O’Brien’s influence in the entertainment world has only grown stronger, transitioning into the digital world with his podcast Conan O’Brien Needs a Friend and expanding into the world of travel shows with Conan Without Borders.
Though O’Brien didn’t hire Ray Romano for his show, his own success as a late-night host and comic trailblazer continues to solidify his place as one of the most influential voices in comedy today.
Why Ray Romano’s Career is a Testament to Perseverance
Ray Romano’s story is one of perseverance. Despite setbacks and rejections, he remained focused on his craft. His eventual success is a reminder that the road to success isn’t always straight—sometimes it’s full of detours and missed opportunities. But those detours can lead to even greater things.
Romano’s rise to stardom didn’t rely on a single moment of serendipity; it was a result of years of hard work, honing his craft, and finding the right platform for his unique comedic style.
Conclusion: The Power of Timing in Hollywood Careers
The entertainment industry is notorious for its unpredictability. Timing, luck, and opportunities often make the difference between success and failure. Ray Romano’s career trajectory serves as a perfect example of how one moment of rejection can lead to greater things in the future. While Conan O’Brien might have passed on hiring Romano, it was the very rejection that propelled him into the role that would shape his career forever.
Both O’Brien and Romano continue to be major figures in the world of comedy, but it’s clear that fate played a hand in guiding their paths. The entertainment industry will always be full of “what if” moments, but it’s those moments that remind us of the serendipity behind great success stories.
5 Unique FAQs About Conan O’Brien and Ray Romano
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Why did Conan O’Brien pass on Ray Romano? Conan O’Brien didn’t feel that Ray Romano’s comedic style aligned with the direction he wanted to take with Late Night. O’Brien was looking for a different type of comic talent at the time.
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What was Ray Romano’s big break? Ray Romano’s big break came when he landed the lead role in Everybody Loves Raymond, a sitcom that became a massive hit and turned him into a household name.
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Did Conan O’Brien regret not hiring Ray Romano? Conan O’Brien has never publicly expressed regret about passing on Ray Romano, but it’s clear that Romano’s success in television was a pivotal moment in both their careers.
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What other successful projects did Ray Romano pursue after Everybody Loves Raymond? After Everybody Loves Raymond, Ray Romano worked on Men of a Certain Age, voiced characters in the Ice Age movies, and continued his stand-up comedy career.
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What is Conan O’Brien’s most famous late-night skit? Conan O’Brien is known for his many memorable skits, including his “In the Year 2000” segment, and his absurd humor, including memorable segments like “Conan Without Borders” and “Clueless Gamer”.
