Stephen Colbert and Conan O’Brien are titans of late-night comedy, known for their sharp humor and enduring friendship. While their on-screen chemistry is undeniable, a lesser-known personal connection ties them together: their fathers’ shared history at the College of the Holy Cross. This heartwarming story, revealed during a 2020 joint appearance on Conan and The Late Show with Stephen Colbert, offers a glimpse into the personal bond that underpins their professional camaraderie.
During the virtual crossover event, prompted by the pandemic’s shift to remote broadcasting, the two hosts uncovered a meaningful coincidence. Both of their fathers graduated from the College of the Holy Cross, a small Jesuit institution in Worcester, Massachusetts. Conan O’Brien’s father, Dr. Thomas O’Brien, was a microbiologist specializing in infectious diseases, while Stephen Colbert’s father, Dr. James William Colbert Jr., served as an associate director at the National Institute of Allergy and Infectious Diseases. The discovery of this shared background sparked a conversation that blended their trademark humor with genuine emotion.
The standout moment came when Colbert shared a poignant anecdote from his early career. While filming a segment for The Daily Show in Arizona, he met an elderly man nicknamed “Bones” Hamilton, a Holy Cross alumnus from the class of 1942. Hamilton revealed he had known Colbert’s father, who tragically died in a 1974 plane crash when Stephen was just 10 years old. Hamilton recounted a college prank involving Colbert’s father, whom he affectionately called “the Silver Fox” for his charismatic charm. The story struck a deep chord with Colbert, who rarely heard such vivid personal memories of his father, and it resonated with O’Brien, whose own father’s Holy Cross connection added a layer of shared history.
This exchange was more than a nostalgic detour; it highlighted the authenticity of Colbert and O’Brien’s friendship. Their ability to connect over such a personal story, while still keeping the conversation light and engaging, reflects the warmth that defines their relationship. The Holy Cross connection serves as a quiet but powerful thread linking their pasts, grounding their larger-than-life personas in a shared sense of heritage.
The 2020 moment also underscored their mutual admiration. O’Brien praised Colbert’s transformative journey from The Daily Show to The Colbert Report to The Late Show, while Colbert acknowledged O’Brien’s pioneering work in redefining late-night through projects like Conan O’Brien Needs a Friend. Their laughter over the Holy Cross revelation, paired with the emotional weight of Colbert’s story, created a memorable snapshot of two friends who share more than just a love for comedy.
In an industry often defined by competition, the Holy Cross story is a reminder of the personal ties that can unite even the biggest stars. For Colbert and O’Brien, this shared history is a testament to the enduring power of friendship, making their on-screen banter all the more meaningful.
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