Jimmy Fallon Says This Celebrity Was His "Most Awkward" Interview Ever

This A-lister put the host through his paces.

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."

Fallon handpicked the star to be his first guest.

Jimmy Fallon at the Peoples Choice Awards in 2018
Kathy Hutchins/Shutterstock

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."

"Yeah, in real life he doesn't even talk much," Fallon responded. He went on to explain that booking guests for a new talk show isn't easy because publicists are hesitant to put their clients into a situation where they don't know what's going to happen. So Fallon had to be strategic about asking someone who would agree to do the show.

"So I was like, 'I want to get somebody A-list,' and I want someone in New York," Fallon continued. De Niro was the first name to come to mind.

Fallon said he'd done some charity work with the Taxi Driver star, so he felt comfortable asking him. "And here's the coolness of Robert De Niro," the host went on. "He didn't have a movie coming out, had nothing to promote, he said, 'Absolutely, yes," as soon as I asked him."

For a guest who isn't welcome back to a different late-night set, check out The One Guest Jimmy Kimmel Banned From His Show.

Fallon's first interview with De Niro was awkward for one specific reason.

Jimmy Fallon at the Macy's Thanksgiving Day Parade in 2019
lev radin/Shutterstock

His first interview with De Niro was stressful, Fallon said, because the star would only give "one-word answers." Doing an impression of the actor, Fallon illustrated how he would only say "yup" and "nope" to his questions.

Fallon also told Cohen that throughout this interview with De Niro, he was feeling very nervous, and it showed.

"It's flop sweat coming down my face," Fallon said. "My hair looked like it had a comb-over…At one point I was delirious, I couldn't even see him…I was just getting loopy, but he's the best."

For another talk show interview gone wrong, check out This Was the Worst Guest The View Ever Had, Former Host Says.

De Niro played a prank on Fallon before he came onto the show.

Robert De Niro at the Hollywood Film Gala in 2012
DFree/Shutterstock

There are no hard feelings between De Niro and Fallon, and, since Fallon took over as host of The Tonight Show, De Niro has come onto the show a few times. During an April 2018 appearance, Fallon revealed that the actor played a prank on him when they were planning that infamous 2009 Late Night interview.

The host recalled that De Niro's publicist had asked Fallon to email De Niro his questions ahead of time. "I sent the questions, like 15 questions to you, and you go, 'Pretty good, what else you got?'" Fallon said to his guest. He then explained that he sent another 15 to the same response, and then another, and so on.

"Now my questions are getting bizarre," Fallon laughed. "And as I'm typing, I got an email from you that goes, 'Ha ha, just kidding. See you on the show.'"

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Fallon and De Niro have laughed about the interview a lot over the years.

Robert De Niro visits "The Tonight Show with Jimmy Fallon" iin 2015
Theo Wargo/NBC/Getty Images for "The Tonight Show Starring Jimmy Fallon

During a 2015 Tonight Show appearance, Fallon brought up the "favor" he'd asked of De Niro back in 2009.

"I gotta say, I had no idea what I was doing," he said of that first episode and rough interview. "I ran out of questions to ask you because you don't even like doing talk shows that much."

De Niro clarified that he didn't mind doing talk shows, depending on host, and assured Fallon that he'd done "a great job."

For a TV guest who didn't make a great impression, check out This Was the Worst Behaved SNL Guest, According to Bill Hader.

Amber Raiken
Amber Raiken is an Editorial Assistant at Best Life. Read more
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