When audiences think of The Colbert Report or The Late Show with Stephen Colbert, they remember the biting monologues, the celebrity interviews, and the unforgettable sketches. But for two decades, one man was behind every camera angle, every cut, and every perfectly timed zoom: Jim Hoskinson, Colbert’s longtime director.
Earlier this month, Hoskinson announced his retirement after an extraordinary career spanning over 3,000 episodes with Colbert. And while directors often remain invisible to audiences, Colbert refused to let him exit without shining a well-deserved spotlight on the man who helped shape his television journey.
oskinson didn’t begin his career in comedy. In fact, his formative years were spent in the news business. He worked at Inside Edition during the 1990s when Bill O’Reilly anchored the program. That job placed him at the control room helm during one of television’s most infamous moments: O’Reilly’s frustrated “We’ll do it live!” meltdown, now a viral clip that still circulates decades later.
After Inside Edition, Hoskinson moved to Fox News, where he spent six years directing news programming. Those years taught him how to handle the fast pace and high stakes of live television. He became adept at balancing the unpredictable — qualities that would prove essential when he stepped into the world of satire.
A Natural Fit for The Colbert Report
In 2005, Comedy Central launched The Colbert Report, giving Stephen Colbert his own spin-off from The Daily Show. Modeled as a parody of conservative cable punditry, the show required a director who could mimic the look and feel of a news broadcast while still playing into the satire.
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Hoskinson was the perfect fit. His years directing O’Reilly-style programming meant he knew exactly how to stage the pomp and polish of cable news — which allowed Colbert to lampoon it with uncanny precision.
Over nine years and 1,446 episodes, Hoskinson helped create the visual identity of The Colbert Report. Whether it was the dramatic camera sweeps, the “serious” anchor desk framing, or the sudden cutaways to Colbert’s exaggerated expressions, Hoskinson’s direction kept the satire razor-sharp.
Transitioning to The Late Show
When Colbert took over CBS’s The Late Show in 2015, Hoskinson came with him. The move was no small transition: late-night talk shows demand a different rhythm than satirical news. Gone were the single-anchor setups; in their place were interviews, musical performances, sketches, and live audience reactions.
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Hoskinson thrived in this new environment. Over 1,600 episodes, he directed Colbert’s nightly mix of political commentary and entertainment. From orchestrating live coverage of presidential debates to staging elaborate comedy bits with A-list stars, Hoskinson kept the production steady through some of the most tumultuous years in American politics.
Colbert acknowledged that steadiness in his on-air tribute:
Emmy Recognition at Last
Though Hoskinson had been nominated for seven Emmy Awards and one Directors Guild of America Award throughout his career, his first win didn’t come until 2025. At the Creative Arts Emmys, Hoskinson finally took home the trophy for Outstanding Directing for a Variety Series — the first directing Emmy ever awarded to The Late Show.
For Colbert and the staff, it was a poetic moment: the man who had quietly steered the ship for 20 years was finally recognized in front of the industry.
A Team Player
Despite his accolades, Hoskinson insisted that his success was never his alone. On The Late Show, he reminded viewers that directing is a team sport:
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That humility, cast and crew say, defined Hoskinson’s leadership style. In a world where egos often clash, he was known for his steadiness and collaborative spirit.
Passing the Torch
Hoskinson’s retirement doesn’t leave The Late Show rudderless. His longtime associate director Yvonne DeMare, who has worked alongside him for much of the past two decades, will step into the director’s chair.
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Colbert introduced her on air, joking, “I’m so glad you are taking over. I have one question. Are you going to be okay if I occasionally forget and call you Jim?”
DeMare quipped back, “I insist.”
It was a moment that captured the show’s mix of professionalism and humor — and reassured fans that Hoskinson’s influence will linger even in his absence.
What’s Next for Hoskinson
So what does retirement look like for a man who’s spent 20 years in the high-pressure world of live television? Hoskinson told Colbert he plans to buy an RV and travel the country.
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Colbert couldn’t resist a joke: “So you’re going to solve crimes, it sounds like?”
Hoskinson chuckled, “That’s not a bad idea.”
The Legacy
When Stephen Colbert bid farewell to Hoskinson, he did so with words that felt simple yet profound:
Hoskinson’s legacy isn’t just the awards or the episodes he directed. It’s the countless moments of comedy and culture he helped bring to millions of viewers. It’s the trust he built with a host who relied on him every night for two decades. And it’s the example he set for future directors like Yvonne DeMare, proving that behind-the-scenes leadership can shape the very soul of a show.
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For fans of Colbert, Hoskinson may not have been a household name. But his work was woven into every laugh, every applause break, and every memorable moment. As he rides off in his RV, perhaps to “solve crimes” after all, one thing is clear: the man behind the camera has left an indelible mark on the world in front of it.
