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Allow Conan O’Brien to Introduce You to Chris Fleming

Chris Fleming built his following one hyper-specific, unhinged YouTube video at a time. Starting with his breakout web series Gayle, where he played a middle-aged suburban mom worrying about Christmas cards and a shoes-off house, Fleming spent the better part of a decade building a cult following through sheer, compulsive output, moving from YouTube specials to Peacock and now, finally, to HBO. His comedy, dense with New England pathology, subur…
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Interview Magazine broke the news in on Friday, February 27, 2026.
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