Jimmy Fallon reveals which actor was his most awkward late night guest

Jimmy Fallon gets a lot of flack for his interviewing skills. We've criticized him on this very sight when it comes to his penchant for cutting guests off, or stepping on a joke that took minutes to build up. He isn't the smoothest in this regard.

That said, Jimmy Fallon is human, and things can get awkward for him during interviews as well. The veteran Tonight Show host opened up about this exact topic during a 2019 interview on Watch What Happens with Andy Cohen.

Jimmy Fallon initially struggled with Robert De Niro

Fallon was asked to reflect on the most akward late night interview of his career, and he came up with a name right away: Robert De Niro. The host told Andy Cohen that he struggled mightily with De Niro, as the conversation seemingly went nowhere.

Fallon conceded that he was relatively new to late night when the interview occurred, but maintained that Robert De Niro did not give him a lot to work with:

"He came on and he was Robert De Niro... Just one word answers and nodding. Like 'Yep,' 'Yep,' 'Nope.'"

Fallon and De Niro have build up better rapport since

De Niro is notorious for being quiet during interviews, and it's easy to sympathize with Fallon when it comes to feeling stuck. Fortunately, for both men, they have built a better rapport over the years. De Niro has appeared on The Tonight Show numerous times since his initial Fallon encounter.

The Oscar winner even opened up about some of the roles he missed out on during his illustrious career. During a 2021 Zoom interview, De Niro told Fallon that he was up for the lead role in the iconic comedy Big, but ultimately lost it to Tom Hanks. Hanks would go on to earn an Oscar nomination for his performance.

It all worked out, though. De Niro collaborated with Big director Penny Marshall on her next film, Awakenings, and was promptly nominated for an Oscar as well. You can watch the full Tonight Show conversation here. Not much awkwardness to be found.