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While Jimmy Fallon now has 12 years of experience in the talk show business under his belt, not every interview he’s done has been smooth sailing. In fact, one conversation that he still stresses out about was with one of the most legendary actors there is. To see which A-lister the host says was the most awkward interview of his career so far, read on, and for more awkward moments on late-night television, check out Kenan Thompson Says This SNL Guest Made the Cast “Extremely Uncomfortable.”

During an appearance on Watch What Happens Live in December of 2011, a caller asked Fallon what his most awkward interview ever was. Fallon revealed that it was Oscar-winning actor Robert De Niro, who was a guest for his March 2009 debut as the host of Late Night. Andy Cohen noted that De Niro is known as a “notoriously kind of difficult interview.”

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